Tuesday, November 21, 2017

Orientation

Sissy going through orientation at her new job at her wife’s law firm.  All of the partners agree she has tremendous potential.

Monday, November 20, 2017

Great Expectations

Sissy’s wife looks back at he and says, “Okay sweetie.  You said you wanted this.  When the first drop of John’s cum leaks out I expect your tongue to get busy.”

Tuesday, November 14, 2017

A Neat Desk Is A, Well...

In less than a week on her new job as a secretary at her wife’s law firm, sissy understands what her boss means when he goes to lunch and tells her he wants his desk cleared when he returns.

Friday, November 10, 2017

Wednesday, November 8, 2017

Monday, November 6, 2017

Walking the Walk

When sissy told her wife she liked wearing women’s lingerie, her wife told her things would be different from then on.  If sissy was going to talk the talk, she’d have to learn to walk the walk.

Saturday, November 4, 2017

Are You Sure?

Your wife looks over at you sitting in the corner wearing your pretty lingerie and asks one more time, “Are you sure you want me to go through with this sweetie?”  Then, before you can even answer, she says, “Never mind,” as she settles down and takes your boss’ entire cock inside of her screaming, “Yesssssssssssss!!!!!!”

Friday, November 3, 2017

Small and Weak

When sissy’s wife brought her boss home for dinner, and then he took her to bed, sissy felt small and weak, especially dressed in her pretty pink sissy maid uniform her wife told her to wear to serve them dinner.  But the next morning, after her wife was sent to work by her boss and he remained for “coffee” and to "discuss things" with sissy, she learned what it meant to be “small and weak.”

Wednesday, November 1, 2017

Sissy Says Goodbye To Mexico - Day Seven

[NOTE - Anyone who is just beginning to read my blog might want to read the following early entries in my blog about my sissy journey before reading this latest entry: A Little More Background - Am I Sure I Should Do This? - I'm Afraid - These - Where It All Started - Then, These - Miss Flo - Caught For The First Time - About My Last Post - Bikini Panties!!! - A Virgin Bride (And Groom) - Exhausted Sissy Needs Stress Relief! - Sissy Marries Cheerleader - Sissy Makes Life With Cheerleader - Cheerleader Discovers Sissy - Cheerleader Accepts Sissy - Cheerleader And Sissy Grow - Cheerleader Asserts Control - Cheerleader Teases Sissy - Cheerleader And Sissy Settle In To New Home - Cheerleader Cucks Sissy - Cheerleader and Sissy Are Mentored - Sissy Offers Context For Cheerleader - Sissy Sees Her Future - Sissy Adapts To Chastity - Sissy And Cheerleader Spend A Weekend Apart – Our Weekend Apart Aftermath  Cheerleader Has A Heart-To-Heart With Sissy - Sissy And Cheerleader's Last Weekend With Andrea - Part One - Sissy And Cheerleader's Last Weekend With Andrea - Part Two - Cheerleader Thanks Sissy - Cheerleader Does A Sleepover - How My Cheerleader Vets Men - Cheerleader Flirts - With Purpose - Cheerleader Is A Happy Girl - Cheerleader Learns  Juggling Isnt Easy - Cheerleader Gets An Itch - My Cheerleader's Summer of Contentment – My Cheerleader and Her Quarterback -  Cheerleader and Sissy Reach Accord (And Satisfaction) - Sissy Catches Up, Cheerleader Goes Sailing - Discovered! - It Was Bound To Happen Sooner Or Later - Quarterback Discovers Leeanne - I Have Good News. And News - Quarterback Is Visiting For Labor Day - Cheerleader Speaks - My New Sissy Life - Kittens Love Cream - Sissy Belongs to Cheerleader - Santa Claus Is Coming To Town - Bath Time - Christmas Shopping Visit Summary - Cheerleader and Sissy's Christmas Surprise - We're Going To Mexico! - Mexico - Day One - First Full Day In Mexico - Day Two - Mexico Heats Up- Day Three - Sissy Confessions- Day Four in Mexico - Surprise Visitors to Mexico - Day Five - Sissy Gets A Reprieve - Day Six - Opening Day And An Explanation - It's Over (At Least For Now) - Sissy's Big Day - Day Six.  These are the previous posts that tell the story about my sissy journey.]
We were up early on our last morning in Mexico, all dressed to go to the airport for our return trip home.  Derek and Samantha were staying an extra week alone, probably as some sort of payback for coming in and taking care of me, as it had dawned on me that Quarterback planned for me to lose my virginity to Derek on the trip.  My Cheerleader was quiet in the morning as we ate breakfast and then said our goodbyes to everyone.  Mercedes gave me a warm hug as we said goodbye and told me she had enjoyed taking care of me during the week.  I was going to miss her.  She was so sweet and never judged me for being a sissy during the entire trip. 
At the airport, my Cheerleader stayed close to her Quarterback, but she remained quiet throughout.  I, more or less, hung around like the third wheel I felt like.  Just as we had on the flight to Mexico, their First Class seats were next to each other and I sat alone across the aisle.  I ended up sleeping most of the way home.  A limo transported us from Dulles back to our house, where I learned for the first time that Quarterback was going to stay for the night before returning home.  Thus, I was relegated to the guest bedroom that first night home.  My Cheerleader declared herself exhausted and so she and her Quarterback went to bed together early and left me to put things away and get settled in the house.  Mostly though, I worried about her, and hoped she and I were going to be okay when we were finally alone together again.
The next morning I woke up early and prepared biscuits and coffee to serve my Cheerleader and her Quarterback in bed.  I had no idea when he’d be leaving, but I fell easily into my role taking care of them whenever he was at our house.  I tapped on the bedroom door before entering and Quarterback called out for me to come in.  When the door swung open I saw my Cheerleader on her hands and knees, much like I’d been two days earlier when Derek took my virginity, and her Quarterback was riding her from behind, pushing her forward and then she’d drive back onto his cock, her heavy breasts swaying back and forth beneath her.  Whatever issues she may have had with her Quarterback the last night in Mexico seemed to be over at this point.  She was moaning and groaning as he fucked her hard.  He smiled at me as he methodically fucked her, leaving me standing by the bed holding their breakfast tray and watching him give my wife what she so clearly needed from him.  I felt uncomfortable, but I also sensed he expected me to stand by and watch him fuck her.  After a few minutes he drove deep inside of her and stopped.  I could see his cock begin to pulse and knew he was filling her pussy with his cum.  She cried out, “Oh fuck yes!  Yes!  I love your cock!  Yes!”  After a few minutes she collapsed beneath him and his spent cock slipped out of her.  He lay down on the bed next to her and held her close and she kissed him deeply with so much passion.  I was struck by the hold he seemed to have over her then, and I actually wondered if I might eventually lose her to him.  After they settled down I served them coffee and biscuits and then left them alone and went back downstairs.  A few hours later Quarterback came downstairs freshly showered and dressed.  He said goodbye to me and told me he hoped I’d enjoyed the trip.  I told him I had and thanked him, although truly I was very worried about how things were going to be between me and my Cheerleader after he left.  A short while later a car came to pick him up and he was gone.
My cheerleader was still upstairs and I wondered if she were going to get out of bed.  A few minutes after I closed the door behind Quarterback, she called out my name.  I went upstairs and found her lying in our bed, naked, partially covered by the sheets.  When I asked what she wanted she smiled at me and said, “You.  I want you.  Come to bed with me.  Hold me.”  I took off the maid’s uniform I was wearing and crawled in beside her in my stockings, panties and bra.  We cuddled and I held her close to me, feeling her breathing on my neck.  Then she kissed me and said, “You know I love you, right?”  My heart melted.  “Thank you,” I whispered to her.  “I love you too.”  She smiled at me then and said, “So?  I guess we each broke a barrier this week, huh?”  I felt embarrassed when I realized what she was referring to.  “I suppose.”  Maintaining her eye contact with me, she asked, “Was it everything you hoped for?”  I didn’t know what to say to her.  I felt uncomfortable talking about it, but I sensed she wasn’t going to let it go.  Instead, I asked her, “Was it everything you hoped for?”  She smiled and said, “And more.  Now you.”  I smiled and said, “And more.”   She laughed and said, “Then I suppose it was worth the trip.  Now, I need something from you baby,” as she nudged my head down and I knew exactly what she wanted.  As soon as my tongue tasted her I knew that she was still full of her Quarterback’s sperm.  I licked and sucked her slowly and softly, feeling her relax to the gentle way that only her sissy husband could please her.  She cooed quietly to me as I licked and cleaned his seed from her, “Oh yes baby!  Yes!  I love the way you do that to me.  I love you so much.”  I said nothing.  I continued licking and kissing her and making love to her pussy in the best way that I knew how, happy to hear her tell me she loved me and feeling less worried about where we were heading as a married couple.  Little did I know what the next few weeks and months would be like for her, and us, as she struggled with her feelings toward her Quarterback and the hold he held over her.





Sunday, October 29, 2017

Sissy's Big Day in Mexico - Day Six

[NOTE - Anyone who is just beginning to read my blog might want to read the following early entries in my blog about my sissy journey before reading this latest entry: A Little More Background - Am I Sure I Should Do This? - I'm Afraid - These - Where It All Started - Then, These - Miss Flo - Caught For The First Time - About My Last Post - Bikini Panties!!! - A Virgin Bride (And Groom) - Exhausted Sissy Needs Stress Relief! - Sissy Marries Cheerleader - Sissy Makes Life With Cheerleader - Cheerleader Discovers Sissy - Cheerleader Accepts Sissy - Cheerleader And Sissy Grow - Cheerleader Asserts Control - Cheerleader Teases Sissy - Cheerleader And Sissy Settle In To New Home - Cheerleader Cucks Sissy - Cheerleader and Sissy Are Mentored - Sissy Offers Context For Cheerleader - Sissy Sees Her Future - Sissy Adapts To Chastity - Sissy And Cheerleader Spend A Weekend Apart – Our Weekend Apart Aftermath  Cheerleader Has A Heart-To-Heart With Sissy - Sissy And Cheerleader's Last Weekend With Andrea - Part One - Sissy And Cheerleader's Last Weekend With Andrea - Part Two - Cheerleader Thanks Sissy - Cheerleader Does A Sleepover - How My Cheerleader Vets Men - Cheerleader Flirts - With Purpose - Cheerleader Is A Happy Girl - Cheerleader Learns  Juggling Isnt Easy - Cheerleader Gets An Itch - My Cheerleader's Summer of Contentment – My Cheerleader and Her Quarterback -  Cheerleader and Sissy Reach Accord (And Satisfaction) - Sissy Catches Up, Cheerleader Goes Sailing - Discovered! - It Was Bound To Happen Sooner Or Later - Quarterback Discovers Leeanne - I Have Good News. And News - Quarterback Is Visiting For Labor Day - Cheerleader Speaks - My New Sissy Life - Kittens Love Cream - Sissy Belongs to Cheerleader - Santa Claus Is Coming To Town - Bath Time - Christmas Shopping Visit Summary - Cheerleader and Sissy's Christmas Surprise - We're Going To Mexico! - Mexico - Day One - First Full Day In Mexico - Day Two - Mexico Heats Up- Day Three - Sissy Confessions- Day Four in Mexico - Surprise Visitors to Mexico - Day Five - Sissy Gets A Reprieve - Day Six - Opening Day And An Explanation - It's Over (At Least For Now)  These are the previous posts that tell the story about my sissy journey.]

***Cheerleader here again.  I felt I should say something about my sissy's post that you are about to read.  The things that she tells about?  That happened to her?  When I first learned of what my ex-husband had done, I was not pleased.  I suppose you could say that it was the beginning of the end.  I am not thrilled that Leeanne is sharing this story.  However, I've done some things, and I've made some changes.  My point is, I understand my obligation to her.  She is, after all, my sissy.  No one else's.  That's part of why I ended things with my ex-husband.  On the other hand, she feels it is important to share the details with the people she shares this blog with.  It means something to her.  And she means something to me.  So I'm letting her share this story.  Try to not judge either of us too harshly.

At long last, with my Cheerleader's blessing, the details about our last full day in Mexico.



First things first.  I apologize for the lengthy delay in posting this.  A lot has happened since our trip to Mexico, and now that my Cheerleader has explained some of it in her recent post, I am going to post my account about our last day and night in Mexico.  Obviously, I would not be posting this account without my Cheerleader’s permission.  Given the recent change in our lives, I am grateful that she has decided that my blog is important to me and that she is now encouraging me to continue to write about our lives, and even participate in it to some extent – at least much more than she ever did.  When I first wrote about the last day and night in Mexico, my Cheerleader was not happy with the way things had gone and did not want me to post such a graphic description of what happened.  Letting what happened take place, and reading my graphic description of the events, were two different things.  She was concerned about me telling the “world” what she and I had done.  So I have held off until she gave me permission.  I think the reality of what I have become hit her in Mexico and then really soaked in after we returned.  I also know that those concerns led, in part, to her ending things with her Quarterback.  He had taken on a very dominant and controlling role in our lives, but it wasn’t until she decided it was too much that the relationship ended.  This issue has been hanging in the air for quite some time and was an ongoing problem between my Cheerleader and her Quarterback, although the relationship continued for a while.  There has always been something about him where she is concerned, and I think I understood what it was.  He provided her an escape from having to be in charge.  Anyway, she made her decision to end things with her Quarterback and so she and I are getting “back on track,” as she says.  Still, I should have posted something explaining why I hadn’t posted anything.  So, for that, I apologize.  Without further ado, I present the last day and night in Mexico.  
You’ve heard of woman’s intuition?  I don’t know if sissies can pipe in to such power, but when I woke up on Day Six of our Mexico vacation, I just had a feeling that the day was going to be extraordinary.  Was I ever right!  I’ll say at the outset of this post that not every moment was what I’d call, comfortable.  Throughout the day I experienced a wide range of emotions, from embarrassed to humiliated to overwhelmed to exultant and to turned on beyond measure, until the day finally ended as one of the most amazing days I could recall spending as a sissy, and maybe even as a person, which noun I use intentionally.  Because right now?  I don’t think it is exactly accurate to call me a man.  But I’ll let others be the judge of that.
It was around 9 a.m. when Mercedes came to wake me up.  She told me I needed to shower and shave before breakfast.  When I returned to my bedroom after showering she helped me into a pink lace full cup bra and matching panties.  My bra cups were filled with my large breast forms.  She then gave me a sheer white babydoll nightie to put on, which kind of surprised me as I figured I’d be dressing for daytime activities.  I asked why and she said it was just for breakfast and the other “girls” were also wearing their nighties.  Right then I began to wonder what was in the offing.  But ever the compliant sissy, I let her help me into the babydoll, after which she applied makeup, attached my hoop earrings, and then secured my pink wig.  I also slipped on my pink high heels. 
“Dressed” for breakfast, I went to join the others on the veranda.  As Mercedes had told me, my Cheerleader and Samantha were also wearing very sexy nighties, although neither of them was wearing a bra, so their full breasts were on prominent display beneath their sheer gowns.  Quarterback and Derek each had on swim trunks.  The four of them were seated around a large coffee table on which there was a mixture of fruit, bread, muffins and coffee, the two women looking very sexy for their men and cuddled up close to them on cozy couches as they enjoyed a beautiful Mexico morning.  Everyone greeted me as I approached.  I felt very exposed and embarrassed to be so nearly naked in front of all four of them.  My sheer lace panties did not conceal my chastity cage, which was even more visible than it was the previous day when I wore no panties, but at least my maid’s uniform skirt had somewhat obscured my caged clitty. 
As I got nearer, Samantha patted the couch where she and Derek were sitting and said, “Come sit by me Sissy.”  Hearing no one instruct me otherwise, I felt compelled to comply with her invitation.  As I sat quite close to her, she smiled, kissed me on my cheek, and said, “You look quite scrumptious this morning Sissy.  Coffee?”  I thanked her, although it felt funny to be called “scrumptious,” and said I would like some coffee.  Samantha poured me a cup and handed it to me.  My sissy antennae were up and searching for any signal that would give me a clue where this breakfast gathering was going.  Unfortunately, no answers were forthcoming.  Instead, the five of us sat together enjoying coffee, breakfast, and the lovely morning.  While I felt out of place, especially as compared to my Cheerleader and Samantha who, as real women, put me to shame in the feminine beauty department, I understood my place as my Cheerleader’s sissy.
After we had eaten and were, more or less, just hanging out, Samantha shifted gears.  Addressing Quarterback, she said, “So, Tom?  I understand that you have agreed to grant me my wish?  That Sissy is mine today?  Is that true?”  Tom was smiling at me when he spoke.  “Yes Samantha.  Sissy is, for want of a better way to describe it, yours for the day.”  Samantha clapped her hands and cried out, “Oh goodie!  This is going to be fun!  Don’t you think Sissy?”  In that moment I was dumbfounded.  I was going to be Samantha’s plaything?  Really?  What did that even mean?  I had no idea, but my tummy was already churning with anxiety.
“Susan?” Samantha said to my Cheerleader.  “I wonder. Now that you’ve learned about your sissy’s blog, what do you think of it?  I mean, it is awfully revealing, isn’t it?”  There was my first clue.  Samantha had read my blog.  Looking at me as she replied, my Cheerleader said, “Honestly?  When I first found out about it, I wasn’t very happy about it.  I thought I’d had an understanding with her that she wouldn’t publicize our private life.  But now, I’ve accepted it, mostly.  She is actually quite careful about concealing crucial details of our identity, so I suppose it is an acceptable outlet for her.”  Samantha replied, “Oh, I wasn’t talking about it revealing your identities or what you do.  I’m talking about how much it reveals about what is going on inside of her little sissy brain.  I mean, did you know about all of her fantasies that she has described in her blog before you read it?”  My Cheerleader looked thoughtful.  “I guess I had not really thought about it in that way.  I wrote off much of what she posts as innocent erotic entertainment.  What are you suggesting?”
 Samantha gently stroked my cheek.  “Do you know what I’m talking about Sissy?  The things you fantasize about?  They aren’t just fantasies, are they?  You long to experience some of them, don’t you?”  ‘Here we are!’ was the thought running through my brain.  Samantha was well prepared to spend her day with me as her plaything.  She had read my blog and was going to test me on some of the things I have shown a strong interest in, but never experienced.  I was embarrassed to be confronted about my fantasies in front of everyone.  On the other hand, I did not get a sense that Samantha would be easily put off if I tried to deny what she said.  In a quiet voice I answered, “I suppose.”  She laid her hand on my thigh and began softly stroking me near the edge of my panties, then moving closer to my caged clitty, fondling me outside of my panties.  “Is it difficult Sissy?” she asked.  “Or do you like it?  Being caged?  Restricted?  Prevented from being able to experience your desire for release?  Does it help make you feel more feminine?  Tell me.”  My Cheerleader was listening with interest as Samantha quizzed me.  This was an important moment.  I could sense it.  Samantha was unlikely to relent until I confessed my deepest and darkest desires.  Did I want this?  I knew the answer.  And yet, when I answered, “Yes,’ in a whisper, I knew it was not the last question I’d have to answer truthfully.  “Yes,” she repeated.  “It does, doesn’t it?  You long to be dominated and controlled by a woman too, don’t you?  You love your wife and she has given you much freedom, but you long to be dominated, isn’t that true Sissy?”  The entire time she was talking to me she was gently stroking my caged clitty and balls through my panties.  I was pounding out of control within my confinement.  I was hyper-conscious that all eyes were on me as Samantha continued her interrogation.  I nodded, worried how my Cheerleader might react to my admission.  “It’s okay Sissy,” my Cheerleader said, as if reading my mind.  “I want you to be honest baby.”  I looked at her.  “Yes ma’am,” I replied in a quiet voice.
“Tell me something Sissy,” Samantha continued.  “Tell me what your most intense fantasy is, that you haven’t experienced yet.”  I was quiet.  I couldn’t say it.  Not out loud.  Not in front of everyone.  Although I sensed that she knew.  As I sat mute, Samantha stood up.  She turned to face me and said, “Scooch over Sissy.  Sit closer to Derek.”  I did as she asked and she sat next to me again, but now I was between her and Derek.  She resumed rubbing my caged clitty and stroking my smoothly shaved thighs.  “Do you want to touch him Sissy?”  I was quiet.  I knew what she was doing.  And I did.  Want to touch him.  But I was embarrassed.  Could I do this?  Right here?  Right now?  In front of my Cheerleader and her Quarterback?  “It’s okay Sissy.  I know you want to.”  Feeling exposed, I confessed, “Yes.  I do.”  Samantha grinned, pleased that I was still with her.  “Go on then.  Take him out.”  Derek was sitting back on the couch with his legs spread wide in front of him, watching me.  I reached over and lifted the waistband of his swim trunks.  Hesitantly, I slipped my manicured fingers inside and felt, for the first time, a black man’s cock.  He wasn’t fully hard yet, but my first touch revealed to me that Derek was thick and big.  I held him, his powerful cock pulsing in my grasp, my breathing quickening as I let down my inhibitions and felt the power exuding from this strong man’s cock.  Time seemed to stand still.  “Take him out Sissy,” Samantha directed me.  I tugged at his waistband and pulled his trunks down, freeing his massive cock for everyone to see.  My bulging eyes must have been a sight for the others to observe as I took in, for the first time, just how big he was.  Derek’s cock was thick and black.  Very black.  And his balls?  Oh my God!  They were huge!  And full!  And tight!  I couldn’t wrap my fingers all of the way around him.  And he was still soft!  “Stroke him Sissy.  Make him hard,” Samantha instructed me.  Under Samantha’s encouragement, I began stroking Derek’s thick member.  Gently.  Softly.  Sensuously.  Coaxing him to grow harder in my hands.  I softly massaged his balls with my other hand.  As I let myself go, I became less concerned that four pairs of eyes were watching me with who knew what sorts of thoughts about me running through their heads.  After I had been stroking Derek for a few minutes, Samantha asked me, “Do you want to taste him Sissy?”  Fuck!  I wanted to.  So much.  But I couldn’t say it.  Not out loud.  Samantha leaned in close to me and whispered so no one could hear.  “We all know you want to Sissy.  But, you have to ask him.  Ask him if you can suck his dick.  Ask him.  Now,” she whispered to me with finality.  I glanced at my Cheerleader.  She knew.  She knew.  She gave an almost imperceptible nod of her head, giving me her unspoken permission.  I wanted this.  I really, really wanted it.  But I couldn’t choke out the words.  Still stroking him, feeling and watching him grow harder and harder, his massive pole standing up straight under my sissy touch, I uttered the words, “May I?”  Derek didn’t respond.  “Ask him Sissy,” Samantha said.  “May I…suck your dick?”  I’d said it.  In front of my wife and her ex-husband.  All of them.  I’d asked this powerful black man for permission to suck his dick.  In front of all of them!  If I ever had any shame about being a sissy, I’d lost it all now.  Silence.  “May I please suck your dick sir?”  Derek cracked the slightest of grins.  “Yeah Sissy.  Suck my dick.”
The moment was here.  I was going to suck a black man’s cock.  I had been fantasizing about this for so long that it was almost as if I had done it many times.  But this was real.  I was going to put this massive black cock inside of my mouth and suck him.  And he was probably going to cum in my mouth.  And my Cheerleader and her Quarterback were going to watch me.  But that didn’t bother me.  Much.  Not then.  Not in that moment.  All I could think of in the moment was that I was really going to suck a big black cock.  Leaning down, my head moving toward his lap, I licked the tip of his thick, purplish black cockhead.  I kissed it.  I opened my mouth, took his plump head between my painted lips and swirled my tongue around the tip.  I was never going to get all of him in my mouth.  He was too big.  Too long.  Too thick.  But I was going to give Derek the best blowjob I possibly could.  In that moment I was craving his cum more than anything.  “Get on your knees Sissy,” Samantha told me.  “Go on.”  Obeying her command to assume a more submissive position, I slipped off of the couch and onto my knees between Derek’s thick, muscular thighs.  He was a big man in every way, while I was a submissive and feminine sissy on my knees preparing to worship him.  I pulled his trunks all of the way off and moved in close to his crotch, grasping his cock in my hands, bringing him to my lips and taking him inside of my hungry mouth.  Now was the time.  I was going to suck this big black man’s cock and make him cum.  His fat cock spread my mouth open wide.  It felt amazing just to have him between my lips.  An involuntary sigh and moan escaped my mouth, revealing to all just how much I wanted him.  Wanted his cock.  Wanted his cum.  I began bobbing up and down on him, making him wet with my saliva, gulping as I took him as deep as I could, all while stroking him softly and massaging his balls.  I licked up and down his shaft, and then dipped down and began licking his balls.  They were so big!  I had to do it.  I opened my mouth as wide as I could and sucked his ballsack into my mouth.  Derek uttered, “Oh fuck!”  As I sucked his balls I masturbated his huge cock, now soaking wet and slick with my saliva.  He was responding to me.  I was getting Derek off!  As if sensing he was getting closer, Derek growled at me, “Suck my dick Sissy!”  I let his balls plop out of my mouth and wrapped my lips around his cock head.  As I began sucking him again, he cupped the back of my head with his large hand and begin pushing me down on him.  Every time I would plunge down on his dick, he pushed me a little bit further.  I gagged a few times as his cock pounded the back of my throat.  The feeling of his massive cockhead hitting me there was unlike any cock I’d ever sucked before.  Suddenly, without warning, he exploded.  And by exploded, I mean he erupted!  Derek unleashed a powerful blast of sperm into my mouth.  There was so much that it immediately oozed out of my mouth even though my lips were locked around his big black cock.  I jacked him off as I sucked him, coaxing every last drop of his thick cream into my mouth.  My Cheerleader gasped as she watched me.  Quarterback exclaimed, “Fuck!”  And as I finished him off Samantha said, “Good girl.  That was very good Sissy.  Now thank Derek.”  Removing my mouth from his cock, I looked up at Derek.  “Thank you sir.”  Derek smiled.  “You doing that again Sissy!”  Embarrassed, I smiled, and replied, “Yes sir.”
Samantha told me to sit back on the couch between her and Derek.  She softly kissed me on the mouth.  “Mmmmm.  Tastes good Sissy.  Did you like Derek’s cum?”  I couldn’t deny it.  “Yes.  I did.”  She pulled me close and whispered in my ear.  “I want you to suck his cum out of my pussy.”  I nearly choked when she said that.  Fuck!  But to be honest?  The moment her words entered my brain I wanted it more than anything and immediately began wishing it would happen.
The five of us sat together for a little while longer, me cuddled between Derek and Samantha.  Samantha was softly stroking my thighs, teasing me near my caged clitty, as if intentionally keeping me in a highly charged sexual state.  I think I would have done anything she asked.  After a while my Cheerleader stood up and declared that she was going to go put on her swimsuit.  She smiled sexily at her Quarterback and held out her hand.  “Wanna come help me pick one out?”  Taking her hint, he said, “Sure.”  They walked off together, leaving me alone with Derek and Samantha.
The next thing that happened will probably define me, as a sissy and a person, more than anything ever will again.  Samantha removed my panties, exposing my shaved, caged clitty, and then stroked me gently near the top of my soft, smooth thighs, just touching my hairless balls with her finger.  After a few minutes of the three of us sitting on the couch alone, her on one side of me fondling me, me close to Derek, sensing his power and strength, Samantha stood up.  She held her hand out to me.  "Come with me Sissy," she said quietly, but in a tone that demanded obedience.  I stood.  She turned to lead me away with her.  To Derek she said, "We won't be too long honey." 
Samantha led me to their bedroom.  Her clothes were spread haphazardly on the chair next to their bed.  Panties, bras, bathing suits, dresses, heels.  As we entered the room she closed the door behind us.  Although she was, effectively nude, since all she wore was a short sheer robe that hung open and concealed nothing, she let her robe fall to the floor.  Standing before me was one of the most gorgeous women I'd ever been near with no clothes on.  Her thick blonde hair fell in waves over her shoulders.  Her full, large breasts, nipples firm and erect, lay heavily upon her chest. 
I wasn't certain how to respond as she stood before me, saying nothing - just looking into my eyes as if deciphering the thoughts and emotions spinning out of control inside my sissy brain.  And believe me, I was spinning out of control.  Imagine, if you can, my sissy state of mind.  As a male, I’d only ever had intercourse with one woman – my Cheerleader.  I’d remained a virgin through the entirety of my first marriage.  Where women were concerned, I’d spent my entire life feeling unconfident.  Now, I was alone with this beautiful naked woman who was way out of my league.  Only a short time before she’d made a reality of one of my deepest and darkest sissy fantasies.  She made me suck a black man's cock.  And to make sure it would always be something I'd never even be able to pretend didn't happen, I did it in front of my wife and her ex-husband.  "So, Sissy," Samantha began.  "Was it everything you imagined?"  I knew what she was asking.  It was as though she could read my mind.  "It was," I paused, "amazing!"  She grinned as she reached between my legs and held my soft balls in her hand.  "Yes.  It was obvious you loved it.  Loved sucking Derek's cock.  Did you love that we all watched you?  Did that turn you on too?"  I was at a loss for words.  Sensing it, Samantha spoke.  "Listen to me Sissy.  I have read your blog, and scoured your Tumblr too.  I know sweetie.  I know what is going on inside of your sissy head.  I know you want to be used.  Controlled.  You want this.  You need this.  And your wife has given her permission to me to help you.  She wants this for you too.  Do you understand what I'm telling you?"  Fuck!  What was she telling me?  Was it what I feared?  What I secretly wanted more than I was ready to admit out loud?  "Let go Sissy.  Give in to me.  I'll take you there.  Today.  Will you let yourself go?  I want you to.  Your wife wants you to.  You want to.  Jump off the cliff and hold my hand Sissy.  I promise I'll look out for you.  Okay?"  I whispered in a barely audible voice.  "Okay."  She smiled and pulled me closer.  She kissed me softly on my mouth, stroking my clitty in its cage.  “Do you like the way I play with your clitty Sissy?”  I was quiet.  “You like when I call it a clitty, don’t you?  Makes you feel like a girl, doesn’t it?”  I stood before Samantha, completely revealed as the sissy I have become.  I nodded and whispered, “Yes.”  With a deft touch of her hand on my shoulder, she directed me to my knees in front of her.  Directly in front of my mouth was Samantha's smoothly shaved, puffy, glistening wet pussy.  Her hand settled on the back of my head and she guided me closer, her thighs open enough to permit me full access.  Needing no further instruction, I licked her.  She tasted good.  I kissed her soft, wet pussy.  I began licking her more, at first gently, making her wetter and wetter, my sissy tongue slipping inside of her slit, enjoying the soft folds of her vagina as my tongue caressed them.  Samantha had a full, large opening, no doubt from being fucked by men such as Derek, who had very large cocks.  As I continued pleasuring her she encouraged me.  "Oh yes Sissy!  So good!  You are so good with your tongue.  Make me cum sweetie.  Make me cum.  Yes!  Oh fuck yes!"  She moaned and sighed as I worked harder and harder to make her cum.  Finally, she pulled my head firmly against her pussy and fucked against my mouth as she came over and over.
She released her pressure on my head and sighed.  I remained on the floor, on my knees, my face wet from her juices, out of breath and resting gently against her pussy.  Samantha caught her breath and then held her hand down to help me stand.  She turned to her dresser and picked up a tube of red lipstick.  Then, in an erotic moment that I know I will replay over and over in my head, she painted my lips a deep bright red.  "I want your lips fresh for Derek when he joins us.  Are you ready Sissy?"  I asked, "Am I going to suck him again?"  Samantha smiled.  "Oh yes.  You are.  And more Sissy.  You are going to be our little sissy today.  I want you to do whatever he or I say.  Just let go Sissy.  Let go."  My internal thoughts were in turmoil.  Did I have a choice?  Of course I did.  No one was making me do anything.  I was completely in charge of moving forward.  All I had to say was 'Uncle!' and it would end.  I was sure of it.  But did I want it to end?  Or did I have to see this through to the end?  This was our last full day in Mexico.  Tomorrow we would be returning to our lives.  Maybe lives that would be forever different, but our day-to-day lives would have to resume in some manner.  "Is he coming in here?" I asked.  She nodded her head.  "Yes.  Any moment.  And I want you to be prepared.  This will be real, but there is also an element of fantasy too, because I know it is what you want.  So?  Are you ready?"  Was I ready?  I was trembling.  I was nervous.  Was it fear?  Excitement?  All of the above?  I wanted this.  I knew I wanted it.  I just didn't know precisely what 'this' was?  What was going to happen?  I'd already sucked Derek's cock.  Was it going to be more of that?  But in private?  Not under my Cheerleader's watchful eyes?  So I could really let go?  
There was a knock on the door.  “Come in baby,” Samantha called out.  The door swung open and Derek walked inside.  He was wearing only his swim trunks.  Derek was a big, strong, powerfully built man.  He’d played linebacker in college.  He strode toward us and pulled Samantha to him and possessed her, his big hand grabbing her naked ass, kissing her full and wet on her mouth.  When they broke he looked at me.  “What are you waiting on bitch?  Suck my dick!  Get me hard so I can fuck my lady.”  The unexpected harshness of his reference to me caught me off guard and stung.  But my reaction?  I said, “Yes sir,” and immediately sank to my knees in front of the two of them.  My fingers were trembling as I pulled his shorts down, releasing his already growing cock.  Did I mention his balls were huge?  Fuck!  I was in a mental fog as I kneeled face-to-face with the most powerful cock I’d ever sucked.  Their eyes were on me as I wrapped my manicured fingers around his thick dick.  I licked him.  The taste of his sperm from earlier lingered.  Slowly, I pulled him inside of my mouth, looking up at him as I did, conscious of the two of them watching me submit to him.  Reveal to him how much I wanted his cock.  He was so thick and my mouth was stretched opened wide as I slid my freshly painted red lips over him, swirling my tongue around him.  I wanted him to love having his cock inside of my mouth.  I wanted to please him.  And I was.  Pleasing him.  He groaned.  He pushed into me.  He said, “Oh yeah!  That’s good.  Suck my black dick sissy bitch.  That’s goooood.”  I’d never been called “bitch” before.  But I found myself loving the sound of it from Derek.  I wanted to be his bitch.  His sissy bitch.  His cocksucking sissy bitch.
After only a few minutes, Derek's cock was rock hard.  Samantha was kissing Derek as I sucked his cock.  She was fondling his cock, pumping him as I tried my best to take as much of him into my mouth as possible - an overwhelming and impossible task.  But just having his thick cock spreading my jaws wider than they had ever been opened was an amazing turn on.  I don’t know how to describe the power he exuded.  Samantha said to me, “Suck his balls Sissy.  He likes that.”  Obediently, I let his cock slip from my lips and ducked lower between his thick, athletic thighs to take his balls into my mouth.  They were huge!  I sucked them both into my mouth, my cheeks bulging with his enormous rocks.  I sucked and swirled my tongue around his sack, saliva leaking out of my mouth and dripping down my chin.  I could tell he liked it though because he said, “Oh yeah!  That’s good sissy bitch.  Don’t stop.”  As I kneeled beneath Derek sucking his massive balls, Samantha moved next to me, her pussy right in my face, and began rubbing her slick cunt with Derek’s hard cock.  “Oh baby,” she moaned to Derek.  “Fuck me.  Fuck me now!” and as she said it she swung one of her legs over me and wrapped her legs around Derek’s waist.  She pushed his cock inside of her as she did so and he impaled himself completely inside of her, all with me on my knees underneath them, sucking his balls.  Samantha’s ass, positioned as she was, was touching my face.  As she began to grind her pussy on Derek’s cock, her ass rubbed all over my face.  It was an incredibly humiliating position to be in, but I loved every second of my submission to the two of them.  Derek was pumping hard inside of Samantha, grunting and moaning as he did.  Samantha whimpered and cried out, “Fuck me Derek!  Your dick is so fucking big!”  I held onto his balls for dear life as he pumped his cock in and out of Samantha.  I could feel it as he was about to explode inside of her.  When he began cumming the sense of his sperm pumping out of his ballsack was palpable to me.  Almost immediately, sperm began leaking out of Samantha’s pussy and onto my face.  When Samantha slipped off of him Derek’s cream flooded out of her pussy and onto my face, his cum soaked dick slapping me on my face as he fell free of her.  Never had I ever felt so completely used and degraded during a sex act.  As Samantha dropped to the floor she pulled me off of Derek’s balls and pushed her soaking wet, cum-filled pussy onto my face and cried out, “Suck his cum out of me Sissy!  Show me what a cum slut you are!”  I slid my tongue inside of her and began sucking and licking Derek’s cream out of her.  Derek stood close to us as I did so, his heavy dick brushing against my face, the two of them kissing while I cleaned his seed out of her pussy.  I sucked her pussy until she began to have an orgasm on my face.  When she was done, she told me to clean Derek’s dick, and so I licked and sucked him until his cock was clean again.  Me?  I was a mess.  My face was covered with their combined cum.  Samantha exclaimed how incredible it had been for her and Derek agreed that it was hot.  Then Samantha told me to go to my room and shower and change into something sexy and then return to them in the bedroom.
In a state of near shock, I went to my room and removed my clothes.  I looked in the mirror and it wasn’t a pretty sight.  Lipstick and makeup was smeared everywhere from the cum bath I had taken.  I turned on the hot water and stepped under the shower, letting the water refresh me and cleanse me of their sex.  Mercedes was waiting for me in my room when I finished.  She smiled at me, almost as if she had some inkling what my morning had been like.  I wondered if she had seen me sucking Derek’s cock on the veranda that morning.  In any event, she had already selected my outfit.  The outfit was my pink lace bra, breast forms, and a pink babydoll that hid nothing.  No panties.  I wore a pink garter and white stockings and my pink high heels.  After fresh makeup was applied, she placed my pink wig on my head and told me that I should report back to Samantha and Derek.  I knocked softly on their door and Samantha yelled out, “Come in!”  When I swung the door open I found the two of them lying close together, naked, on the bed.  Samantha whistled at me and told me to come join them.  I walked closer, very self-conscious of Derek watching me walk in my high heels, my caged clitty on full display.  I felt so so sissy in front of them.  Samantha was stroking Derek’s cock as it lay heavily on his lap, so big even in its softened condition.  She told me to come onto the bed with them.  I crawled on, unsure where I should position myself.  “Kneel there,” Samantha said as she pointed between Derek’s thighs.  I squatted on my knees, my clitty right there in front of them.  Derek looked at it and chuckled.  Samantha said, “Touch him Sissy.  Feel how powerful a real man’s cock is.”  My hands trembling from nervousness, I touched him.  His black skin was soft, yet tough.  I slowly rubbed his long shaft, feeling him respond to my touch.  I was enthralled at the contrast of my white fingers with red painted nails against his black cock.  As I grew more comfortable I took him in both hands and softly massaged him, slowly moving my hands up and down his shaft, stroking his balls gently with my fingernails, loving how he was responding to me, growing harder and harder as I masturbated him.  The two of them were watching me reveal my utter fascination with Derek’s cock.  Without being prompted, I leaned closer and licked him.  When no one told me to stop, I licked him some more.  Soon I had his cock wet all over from licking up and down his shaft.  I wanted his cum again.  I wanted him to go inside my mouth while I sucked him. 
But Samantha had a different idea.  As I worshipped Derek’s cock, now thick and hard from my attention, Samantha said, “You’ve never been fucked, have you Sissy?”  I hesitated at her bluntness.  “No,” I admitted, fearing what she was about to suggest.  “But you wear a plug don’t you?  So you know how good it feels when your Sissy cunt is filled with something, don’t you?”  ‘Oh fuck!’ I thought to myself.  She was going to do this.  She was going to let Derek fuck me!  He was so big!  How would I do this?  I nodded and whispered, “Yes.”  Then she said, “A real cock feels so much better.”  I said nothing.  I continued to massage Derek’s cock.  “Turn around Sissy,” Samantha said.  “On your knees, face down and ass up.  It’s time for you to lose your virginity,” she declared simply. 
Scared and worried about what was about to happen, I nonetheless complied.  I never thought of saying I didn’t want it.  I wanted it.  So much.  I’d fantasized about this so many times in the past.  It was time to ‘man up’ and let it happen now.  As I kneeled on the bed, my sissy pussy up in the air, exposed for Derek to take my virginity, I tried not to think about how much it was going to hurt.  Samantha spoke soothingly to me, as if to help me through it.  I felt her hands on my ass cheeks, softly rubbing me.  “I’m going to rub some lube on you Sissy.  It will help you accept him.”  I felt her fingers, covered in thick, cold, wet lubricant, rubbing around my entry, covering me with a large amount of the slick gel.  She rubbed it inside of me, inserting her fingers inside and opening me with them, greasing me thoroughly.  I was so scared.  I was about to be fucked for the very first time.  By a big and powerful black man with a very big cock.  I wondered if my Cheerleader even knew this was happening.  What would she think?  But honestly?  None of what I thought mattered in that moment.  I was so ready for this.  I wanted it.  Samantha leaned in front of my face and whispered, “Are you ready Sissy?”  Fear and anxiety was all over my face I as whispered back, “Yes.  I’m ready.” 
She smiled at me and said, “Okay baby, do her.”  Derek’s powerful hands grabbed my ass cheeks as he positioned himself behind me.  Then, I felt it!  His thick helmet pressed up against my opening.  He rubbed it all around me, covering his dick with the gel before penetrating me.  I don’t know if it was instinctive or what, but I swished my ass back and forth on him.  His hard cock head was teasing my sissy pussy.  And then it happened!  He pushed forward and, for the first time, I realized the pain I’d feared was more than real.  I cried out involuntarily as he pushed his cock head just inside of me, opening my pussy wide.  Samantha soothed me.  “It’s okay Sissy.  It’s okay.  He’s going to go slowly.  The first part hurts the most.  Just relax.”  I looked into her reassuring eyes, my own filled with tears from the jolt of pain I’d felt when Derek entered me.  He stopped pushing with his cockhead just inside of me.  I adjusted to the sensation of him in me, thicker than any butt plug I’d ever worn, but also different because he was real flesh.  The sensation of having something alive inside of me was new and amazing.  As if signaling to him that I was ready, I swished my ass again.  He slowly pushed forward, deeper and deeper, filling me, stretching my pussy wider and wider.  I cried out again.  It hurt.  And yet, I wanted him in me.  He stopped after I cried out and Samantha asked if I was okay.  I was fighting to keep my breath, but nodded and whispered, “I don’t know.  It really hurts.”  I don’t know exactly how far inside of me he was, but the sense of accomplishment I felt to have taken him as far as I had was incredible.  My eyes were locked on Samantha as she watched me being taken for the first time.  Just then I felt Derek begin to withdraw and I cried out, “No!  Don’t!  Stay!”  They both laughed.  Samantha smiled at me and said, “He’s not stopping Sissy.  He’s just getting started.”  As she said that he pushed slowly back into me again, still not all of the way.  I cried out again.  It hurt being stretched open by his thick cock, but I didn’t want him to pull out either.  He remained still, holding at the depth he had reached.  His cock was pulsing inside of me.  He slowly withdrew and slowly pushed back again, coaxing a grunt from me as he took a little more territory.  Then, he slowly withdrew again, and this time I prepared myself for the next assault.  Derek, true to Samantha’s word, was taking his time and trying to be gentle, although he could only be so gentle with such a thick and hard cock.  A cock like Derek’s takes what it wants, and I was becoming more and more willing to give.  He moved slowly in and out of me, never reaching more than a few inches, but ‘Oh my God!’ did those few inches feel amazing.  I could feel the wetness as he fucked me, in and out, in and out, so slowly and carefully as he penetrated me, in and out and then, suddenly, I felt it.  I could feel him about to cum inside of me.  His cock was pulsing harder.  Without thinking of what I was saying, I begged, “Cum in me Derek!  Please!  Cum in my pussy!”  He growled, “Oh yeah Sissy.  You have a tight little cunt.  I’m going to cum all inside your little bitch ass!” A rhythm began as he pulled out and then pushed back inside of me.  He was fucking me now.  He was fucking me.  I was being fucked.  By a big and powerful black man.  I’d read how women changed when they were fucked by a big black cock.  I had believed it was a real phenomenon.  But feeling was truly believing.  I was being fucked and, in that moment, all I wanted was to feel his sperm filling me. Then, as if my wishing for it made it happen, his cock seemed to grow inside of me as the first eruption exploded, filling me with hot sperm.  Oh fuck!  It was so incredible to experience the sensation of taking a real man’s seed.  He pulled back about halfway and kept pumping out his load.  So much!  So much cum filling me!  Then, too quickly, it was over.  I was panting from the exertion of being fucked.  Samantha was grinning victoriously at me, so obvious was it that I loved it.  He stayed inside of me for a few minutes, softening, while I gathered myself.  Then he began to ease out and when he came out of me he made a loud plopping sound, releasing a flood of his jizz down my crack that covered my clitty.  Emotionally exhausted, I collapsed on the bed.  Samantha soothed me and told me I had been great.  I suppose I heard her, but truthfully, all I felt was spent.  I must have fallen asleep right away.  
When I awoke several hours later, I was alone in their bed.  My ass was sore.  I mean, it hurt, and yet, didn’t hurt.  It is difficult to explain, but despite the soreness, I felt, well, fulfilled.  Happy.  I crawled off of the bed and gingerly walked to the door.  When I opened it I saw the four of them sitting together on the veranda by the pool, everyone in casual clothes.  It was evening.  Our last night together.  I wondered if my Cheerleader knew yet.  Or had she always known?  I went to my room and took off my clothes and got in the shower again, my third of the day.  The warm water felt great.  I just stood there alone and then began to laugh.  I had been fucked!  I couldn’t really believe it, but I had been fucked!   In that moment all I could think of was that I wanted it again.  And again.
Mercedes was waiting in my bedroom when I got out of the shower.  She smiled at me, almost as if she knew?  I don’t know.  Maybe it was me.  But I just thought she could see by looking at me that something had changed.  She had an outfit lying on my bed, ready to dress me to join the others.  It was my short pink maid’s dress and black petticoat.  Of course, garters and stockings, but no panties.  My caged clitty was going to remain on display.  She helped me dress and then applied fresh makeup and my pink wig.  Then she told me there was one more thing Senor Tom had told her to have me wear.  She went to the dresser and when she turned toward me she was holding my fluffy kitten tail and the butt plug to attach it to.  I asked, “Really?”  Mercedes said that his instructions were clear.  On my last night I was going to serve the others.  And this was how he wanted me dressed.  Mercedes sized me up and said, “You look beautiful Sissy.  Time to go.  Have fun.”  I smiled and nodded.  Yes.  It was time to go and perform.  After all, I was the sissy and the odd, ah, girl, out for the night.  Our last night in Mexico.  I wondered how it would all end.
I closed my bedroom door and slowly walked toward my Cheerleader, her Quarterback, Samantha, and Derek.  They watched me approaching them, my sissy petticoats swishing as I walked sexily in my pink high heels.  I was conscious that my clitty was swinging freely and openly as I approached, and wondered if they could see my kitten tail fluttering behind me.  Not certain what was expected of me, but assuming Quarterback intended me to serve as their maid for the evening, I paused when I neared them and dipped into a full curtsy.  When I did, Samantha exclaimed, “Oh my!  Isn’t that the cutest thing!  Sissy!  You look adorable!”  I said nothing.  I am sure I turned bright red.  I felt exposed and humiliated as I stood before them.  My Cheerleader was silent, but watching me closely.  Did she know?  Had they been talking about how I’d earlier begged Derek to fuck me?  To cum inside of me?  Worse, had they heard me?  No one said anything, but I felt they all knew I was no longer a virgin.  “May I refresh your drinks?” I asked.  Everyone said they would like another drink.  I took their order and returned to the kitchen where Mercedes helped me prepare their drinks.  I then returned and served them.  Afterward, Quarterback pointed to the floor next to him and my Cheerleader and said, “Wait here Sissy.”  I went to them and settled on my knees and haunches beside them, waiting for further instructions. 
They all chatted as though I were not even there.  Mostly, they talked about high school days.  I was familiar with the people they talked about, but being younger than them I was not intimately familiar with what they were talking about.  After a while Samantha stood up and announced that she was going for a swim.  The sun was setting.  She removed her white top and shimmied out of her shorts.  This beautiful and well-built blonde stood before all of us wearing a sheer white bra and matching thong panties, completely unashamed for all of us to be watching her.  She then deftly unhooked her bra and let it fall to the ground and slipped her thong off too.  “Who’s coming in with me?” she asked.  Then, pointing to my Cheerleader, she said, “Come on Susan, let’s go!”  My Cheerleader hesitated, but then her Quarterback said, “Go on.  I’ll join you in a minute.”  So my Cheerleader stood and then, she slipped off her blouse and stepped out of her shorts.  Beneath her clothes she was wearing a red satin bra and matching French cut panties.  As she stepped toward the pool, Samantha said, “Uh uh!  Off!  No messing up that pretty lingerie sweetie!”  My Cheerleader glanced to her Quarterback, as if asking for permission, and he slightly nodded his head.  So my Cheerleader somewhat shyly slipped off her bra and panties too.  She was not as bold as Samantha.  The two beautiful women were naked in front of their men, who were enjoying the show.  Meanwhile, I was kneeling meekly right next to Quarterback as he exercised his dominance over my wife.  Samantha grabbed my Cheerleader’s hand and tugged her toward the pool.  Together they dove headlong in, their beautiful bodies piercing the water and creating a huge splash.  They came up laughing and splashing each other, their full, naked breasts bobbing sexily on the surface of the pool.  Derek said to Quarterback, “Man!  Your woman is hotter now than she was in high school!  And she was pretty fucking hot then.  I’d love to tap that shit brother.”  Quarterback laughed and said, “You’re right.  She is hotter than ever.  But you stay away from her.  I let you have her Sissy.  Be satisfied with that.”  Derek said, “That’s alright.  I’m just saying, your woman is looking mighty fine.  Sissy does have a tight ass.  And she knows how to suck dick.  I’ll give her that.”  I was soooo embarrassed and humiliated listening to Quarterback and his high school buddy talk about me in that way.  But truth?  I also loved it!  What I really wanted was for Derek to fuck me again.  So much!
After a few minutes Samantha yelled out, “Come on you two!  In the pool!”  Quarterback and Derek stood up and walked toward the pool, but before they could dive in Samantha shouted, “Lose the shorts boys!”  They laughed, then looked at each other and dropped their trunks right there before jumping in.  The two of them were already nearly hard and their big cocks hung heavily between their thighs.  They each dove in and went right for their women, grabbing them and pulling them close.  The women responded, wrapping their arms around their necks and their legs around their waists and kissed them full on their mouths.  Meanwhile, I was kneeling submissively in my spot on the pool deck watching them cavort in the pool.  I felt very small and subservient, almost as if I didn’t matter.  I wondered if that was intended.  The four of them carried on for quite a while as I watched them from my lonely spot.  Samantha was a major instigator in their frivolity.  I felt like a voyeur watching my Cheerleader playing so freely and openly.  Her nakedness in front of them seemed natural.  She and I had never done anything like that, but now she was so free sexually.  As I watched, I noticed Samantha make a move toward my Cheerleader.  Suddenly, she was kissing her.  Hard.  On her mouth.  And my Cheerleader was responding in kind.  They kissed in earnest as their men watched with rapt attention.  Two beautiful women kissing is as erotic a sight as two men could hope for.  As for me?  I was stunned to see my Cheerleader letting go like that.  From where they were in the pool, I couldn’t make out their conversation, but I could tell that Samantha was talking animatedly to my Cheerleader, who kept shaking her head “No.”  Then, Quarterback said something to her, and she looked at him and I could read her lips say, “Really?”  He nodded his head and she said, “Okay then.”  She turned toward Samantha and held out her hand.  Then, unbelievably, Samantha led my Cheerleader to the pool steps and up out of the pool.  “Sissy!” Samantha called to me.  “Bring us towels.”  I quickly stood, grabbed two towels and gave one to each of them.  She said to me, “Look after the boys while we’re gone Sissy,” and then she led my Cheerleader to her and Derek’s room.
I was, to be frank, stunned.  Was my Cheerleader about to do what it appeared obvious she was about to do?  Make love with another woman?  I mean, she and I had been together with me as her sissy, making feminine love.  But this was new.  At least as far as I knew.  It then dawned on me that I was now alone with Quarterback and Derek, who were just exiting the pool.  They were laughing as they approached me.  Quarterback told me to go get them a beer.  I replied, “Yes sir,” and went to retrieve their beer.  When I returned to give them their beers, they were sitting down.  Neither had put swim trunks back on.  Quarterback told me to kneel in front of them, so I squatted down and waited for my next instruction.  I felt so uncomfortable kneeling in front of them.  They were just shooting the breeze.  But me?  I was right in front of them so that the only thing it seemed I could do was stare at their cocks.  They are both quite large.  I would be looking at Derek, then feel weird because it seemed I could only stare at his cock lying heavily between his thighs, and turn my eyes toward Quarterback and find myself doing the same thing with him, then back to Derek.  Meanwhile, I’m kneeling I front of them wearing a pretty pink maid’s uniform, wearing a kitten tail, and showing off my caged clitty to them.  I know they could tell how uneasy I felt, but I think they were enjoying my torment. 
Then Derek spoke to me.  “Come here Sissy,” he said in a commanding tone of voice.  I crawled to him.  He lifted his hefty meat and waved in my face.  “You want to suck it?” he asked.  I said nothing.  I felt humiliated in front of Quarterback.  Why?  After everything I’d done?  I don’t know.  I just did.  Then Derek said, “I wasn’t really askin’ Sissy.  Suck my dick!” he ordered me. 
I don’t know that I can describe the odd mix of shame and yearning I felt in that moment.  Knowing that I was about to suck a big black cock in front of my Cheerleader’s ex-husband and that he had basically arranged for this to happen, I felt embarrassed beyond measure.  And yet, I wanted Derek’s cock so much!  I leaned in and grasped him gently in my fingers and began a long, wet, sensuous blowjob that I know he loved.  At a certain point in giving Derek his blowjob it hit me that I was even enjoying the fact that Quarterback was watching me.  I will admit that I put on quite a show for him, licking Derek up and down, sucking and licking his balls, and letting him know how much I loved sucking his dick by moaning and slurping him loudly.  When he came, it was a flood that I only partially successfully contained within my mouth.  Much of it oozed down my chin, but I licked it off of my fingers, and did not waste any.  When I was finished Derek looked down at me and said, “I give you this Sissy.  You damn sure can suck dick.”  I sat back on my haunches and smiled at him.  Then Quarterback spoke.  “I’m next.”  I jerked my head quickly toward him.  He was stroking his cock and crooked his finger to me.  “Come here Sissy.  Do me too.”  While the cats were away, it seemed the mice were going to play.  Don’t think it was lost on me that while my Cheerleader was experiencing her first time with a woman, I had been left to take care of their men.
Obediently, I crawled to Quarterback and took his hefty cock into my grasp.  I could feel his eyes burning into me as I crawled to him.  He was hard already, apparently turned on from watching me suck Derek.  I looked up at him and smiled.  He grinned back at me.  In that fleeting moment I considered what we had been through.  He had, more or less, taken over being my Cheerleader’s main man, even though she still saw her other men.  He had also taken significant control over me.  And, more or less, I liked it.  Maintaining eye contact with him, I licked the length of his cock, ending by taking his thick head into my mouth and swirling my tongue around it, moaning my appreciation for him as I did so.  I gave a few quick head bobs up and down on him, taking him as deep as I could, even causing a self-imposed gag.  When I did he exclaimed, “Fuck!” My mouth was watering from the gagging and I used that wetness to slobber up the full length of his dick.  Then, in a quick motion, I dipped low and sucked his balls into my mouth, stroking his cock hard as I did so.  Quarterback groaned as I sucked his balls into my mouth, coating them with saliva.  “Oh fuck Sissy!” he growled.  “Fuck!”  Encouraged, I ramped things up.  I let his balls plop free and began sucking his dick hard, jacking him off into my mouth, letting him know I wanted his cum.  He began fucking my mouth and then he let it rip, spraying cum down my throat.  It was a huge load.  I was so turned on by then I lost control and he slipped out of my mouth.  When he did, a huge blast of his semen sprayed my face, coating me with his sperm.  Instead of taking him back inside of my mouth though, I kept jacking him off, making him spray more cum onto my face, greedily rubbing his cummy dick all over my face. 
When it was over, I looked up to gauge his approval.  But he wasn’t looking at me.  When I turned to see what he was looking at, I saw my Cheerleader and Samantha standing there.  They had walked up while I was sucking off Quarterback.  I didn’t know how much they saw, but if they saw the end, they saw enough.  The look my Cheerleader gave me told me she wasn’t exactly happy about what she saw.  But all she said to me was, “You should probably go get cleaned up.”  I stood and said, “Yes ma’am,” and left them to go to my room, humiliated to have been caught behaving like such a hungry cock slut for my wife’s man.  As I walked away she said, “You may as well pack too.  We’ll be leaving for the airport in the morning.”  And so, just like that, I’d done something to cast a pall upon our vacation.  I didn’t know precisely why in that moment, but I knew my Cheerleader wasn’t happy with me.
I showered and changed into a nightie, then began to organize my clothing to pack for the trip home.  After a while I decided to check on the others.  My Cheerleader and Quarterback were not by the pool – only Derek and Samantha.  They were cuddled on the couch, Derek still naked, Samantha stroking him as her head lay on his shoulder.  They greeted me as I approached.  Samantha told me my Cheerleader and her Quarterback had gone to pack and go to bed.  I asked if she was mad at me.  Samantha said she didn’t think so, but that I had maybe caught her off guard with what she’d seen me doing with Quarterback.  In fact, she said, if anything she thought my Cheerleader might have been mad at him instead.  I hadn’t considered that possibility.  Samantha then told me to sit down with them, on the other side of Derek.  There wasn’t much room on the other side of him, so when I sat I was close to him, feeling his warm skin touching mine.  I could feel Samantha watching me.  She reached across Derek and took my hand in hers, then moved it to Derek’s cock.  Together we stroked him and got him hard again.  Then, she mounted him and took his cock inside of her and began slowly fucking him while I watched.  She seemed to take all of him without effort and I knew that I had a long way to go before I’d be able to accept all of his cock inside of me.  I wondered if I’d ever have another opportunity to have him inside of me, since this was our last night.  After several minutes Derek tensed up and Samantha held him tightly to her breasts.  He was cumming inside of her and she was relishing the sensation of being filled with his sperm.  She sat straddled over his lap for a few minutes and then told me to get on my knees on the pool deck.  She swung off of Derek and stood over me with her legs spread wide and I watched as the first glob of his semen oozed out of her pussy and then I did what I knew she wanted.  I opened my mouth and covered her engorged pussy lips and began sucking his cum out of her.  I loved the way their combined fluids tasted and I loved making Samantha feel good.  When I finished cleaning her I also licked Derek’s cock clean.  We sat together a while longer and then they went to bed.  Samantha told me she had enjoyed her day with me and hoped I liked it too.  I assured her I loved it and that it had been a day I’d never forget.  She laughed and agreed, “A girl never forgets the day she lost her virginity.”
I went to bed alone that night, worried about the next day.  I was certain that my Cheerleader was angry with me.  As it turns out, she was more angry with her Quarterback for the way he used me, although she was also irritated with me because she felt I had been too slutty.