Monday, July 10, 2017

Party Girl

After an evening spent serving drinks to the guests, suddenly sissy found herself the center of attention….

Saturday, July 8, 2017

Her Secret

Why is she smiling?  Because she has a secret.  Shortly after her wedding, she feminized her husband.  Now, whenever she wants to relax, her sissy husband takes very, very good care of her.  Sometimes, what you can’t see in a photo tells the whole story.

Teaching Strategies That Work

At The Vera Wang Institute for Male Modification, a/k/a "Sissy School", there were often two teachers for each class, a teaching strategy that was by design to encourage the trainees to work extra hard to earn their grades and, in the process develop more quickly into the compliant sissies their wives were paying good money to have them become before returning to to the marital home.

Sunday, July 2, 2017

Party Girl

The first few parties where sissy was put on display to serve the guests, she was less than receptive to her wife’s (and the guests) expectations.  However, she has since come to relish being quite the center of attention at her wife’s business parties.

Saturday, July 1, 2017

Friday, June 30, 2017

Thursday, June 29, 2017

FaceTime

When sissy's wife's boyfriend FaceTime’s her while her wife is worshipping his cock, sissy sometimes can’t tell whether her wife is performing for her man, or her sissy.

Wednesday, June 14, 2017

Just A "Little Kink"

Your wife had agreed that you could satisfy your “little kink” of wearing lingerie and dressing like a woman, playing like her maid when you returned home from work.  She’d also hinted that there would be other changes to your life as well.  But you hadn’t considered that you’d come home to work to find her with your best friend.

Tuesday, June 13, 2017

Control

Not that her sissy husband wouldn’t happily suck her boyfriends cock all on her own, but sissy’s wife enjoyed it so much mire when she controlled the action...

Sunday, June 11, 2017

The Sissy Voyeur

Sissy knew she was being naughty peeking in on her wife and her lover, but she found their lovemaking irresistible...

Leadership

When you’re valedictorian of the graduating class at The Vera Wang Institute of Male Modification, a/k/a “Sissy School,” certain responsibilities toward the headmaster are incumbent upon you.  Sissy Leeanne takes her leadership role toward the other sissies seriously.

Thursday, June 1, 2017

Foreplay

She loved the foreplay they had developed.  Her sissy getting her man ready while she watched.  Knowing that soon sissy would guide her man’s hard cock inside of her and then, obediently, wait until they were sated and then provide her tender and loving cleanup duty to finish her off.

Wednesday, May 31, 2017

A Clean House Conundrum

It’s difficult, sometimes, to get all of the housecleaning tools to stay put in the pantry before you close the door.  At times like that Mistress has to take extreme measures.

Saturday, May 13, 2017

Cheer Team Initiation

Sissy had always wanted to be a member of the cheer team.  Finally, she convinced her older sister to sponsor her onto the team.  Although the other girls were reluctant at first to let a guy join the team, when they saw how pretty sissy filled out their uniform, and how athletically she performed the cheers, they finally relented and agreed to let her join the team, but on one condition.  Sissy had to do what every other new girl did before acceptance as full members of the team.  Sissy had been hoping they wouldn’t waive that requirement.

Purpose

The sweetest intimacy for sissy is pleasing her wife's lover while he fucks her.

Sunday, May 7, 2017

Date Night

Their wives learned early on in their friendship that when they went on dates with their boyfriends, it was best to secure their sissies in a manner that restricted the mischief they were able to get into...

Wednesday, May 3, 2017

Sissy's Days In The Stacks

Sissy loved spending her days in the library, soaking up all of the knowledge surrounding her.

Monday, May 1, 2017

Sissy's First Day As A Secretary

On her very first day on the job as a secretary at her wife’s law firm, sissy learned why her wife had told her that work would be the one place she would not be required to wear panties.  Apparently the other partners had made as a special condition of sissy’s employment - Anywhere.  Anyone. Anytime.

Monday, April 3, 2017

Opening Day and An Explanation

It's Opening Day for baseball everyone!  Yay!

I also owe everyone an explanation.  I know I have been absent on this blog.  The trip to Mexico was, to say the least, a major event in my cheerleader's and my life.  I don't think either of us properly calculated how much it would affect us, especially the last full day and our departure day, which I have not posted about yet.  Duh!  I have written about it though.  However, once my cheerleader read what I'd written, she realized how she might feel if I published it on the Internet and stopped me.  As she explained it to me, it was one thing for me to experience what I did, but it was altogether different for me to share it with the world, even if anonymously.  Whether I ever post it will depend upon her.  She is visiting her quarterback this weekend and I expect they will hash it out then.  He wants me to  post it.  But it is, ultimately, her decision.  Overall, things are still good between us.  We did have a bump or two right after the trip.  And I probably should have posted something explaining the lack of a  finishing post for the Mexico trip before now.  I just haven't been in the right frame of mind though given what was going on.  I hope everyone will understand.  Now, let's enjoy some baseball?

Thursday, February 23, 2017

Sissy Gets A Reprieve – Day Six

This post is going to be short.  Quarterback has not always been pleased with the lack of promptness of my posts during our Mexico vacation.  But this morning, as we moved into our last full day in Mexico, he told me I could wait to post about the details of Day Six.  He wasn’t being altogether altruistic.  He was being more practical.  First, I don’t have the time to write today, and he knows it.  I’ve been, well, otherwise occupied.  Second, he wants a detailed accounting of Day Six and that just can’t be done on the day the events have, and are, occurring.  So, sit tight and I’ll tell all.  Because I have to.  And because I want to.  Patience.

Kisses,

Leeanne


Surprise Visitors To Mexico - Day Five

[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.  These are the previous posts that tell the story about my sissy journey.]
I was up early this morning because I was fretting about being behind on my posts.  Quarterback was being nice about it, but I could tell he wasn't pleased that I let a day get away from me.  I finally fell back to sleep though, until I was awakened by Mercedes with a message.  "Senor Tom wants you in his bedroom Sissy.  Now."  As I awoke, I could hear sounds from cheerleader and quarterback's bedroom, especially from my cheerleader.  I knew what they were doing.  "Are you sure?  Now?" I asked.  Mercedes smiled.  "Yes Sissy.  Now."
Wearing the pink babydoll I wore to bed, I went to their room door and softly knocked, to be sure quarterback really wanted me to enter.  In a gruff grunting voice, quarterback said, "Come in!"  As I swung the door open I was treated to a vision of my cheerleader on her hands and knees, quarterback behind her literally plowing her pussy, her full breasts hanging beneath her and swaying back and forth from the repeated pounding she was receiving.  She was panting and moaning as her quarterback fucked her viciously, but in a way she was clearly enjoying.  Quarterback didn't say anything to me.  He just looked at me with an expression that seemed to say, 'I own your wife Sissy!'  And, in that moment, he did, and I knew it, but also was okay with it.  I loved seeing my cheerleader experiencing such pleasure.  I loved seeing her fulfilled and happy.  It just does something for me.
I stood watching, not knowing what else to do.  My cheerleader must have sensed her quarterback was about to cum and she began encouraging him, all while looking directly at me.  "Yes!  Yes!  Yes!  Fuck me!  Fuck me harder!  Cum in me!  Oh fuck!  Yes!  Yes!  Yes!"  And with her last utterance, she collapsed beneath her quarterback, who remained inside of her as he continued to empty his balls.  Both of them were out of breath.  Me?  My clitty was straining against its chastity cage.  Then quarterback spoke.  "Come here Sissy."  I walked to the bed.  As I did, he withdrew his spent cum-coated cock out of my cheerleader.  As he pulled out a thick load of his sperm began oozing out of her.  He told me to come clean his cock off, and so I crawled onto the bed and took his soft, but still plump, cock in mouth and sucked him clean.  Then quarterback said, "Clean your wife Sissy," as he fell back on the bed, pulling her over to his side and onto her back.  She let her legs fall open to give me access and made eye contact with me as I positioned myself between her thighs to begin sucking quarterback's sperm out of her pussy. 
When I finished, quarterback told me to stand by the bed, still in my babydoll and feeling very naked and exposed in front of him and my cheerleader, but also feeling a bit uncomfortable as my cheerleader lay naked in her quarterback's strong arms.  He said he wanted to talk to us, to see how we were doing.  He wanted to know if we were enjoying the trip and how things had gone so far.  My cheerleader spoke first.  "You know I've enjoyed our time together."  She reached over and stroked his cock.  "You know I can never get enough of this."  Quarterback laughed.  "Yes babe.  I know that."  Then, to me, he asked, "How about you Sissy?  Are you okay?"  I looked at my cheerleader, to gauge her response, and then quietly said, "Yes.  This has been good.  Thank you."  Quarterback looked at us and then said, "Good.  Because something is going to happen today, and for the next few days of our trip that I haven't mentioned before, and I want to give you advanced notice so you can prepare yourselves."  Cheerleader immediately asked, "And what is that?"  Quarterback replied, "Before I tell you, I just want to emphasize how careful I have been to protect both of you.  I only wanted to make this a memorable trip where each of us can see what our limits are."  Cheerleader interrupted him.  "Stop!  Tell me!  You're worrying me now."  He brushed her face and leaned over to kiss her on the forehead.  "There is no need to worry.  I promise everything is going to be fine.  But I need to know the two of you are going to be okay.  Here it is.  We're having company today.  An old friend of ours is coming to stay the last two days of our trip.  And he's bringing his girlfriend."  Hearing this made my stomach flip.  My cheerleader asked, "Who?"  Quarterback hesitated, and then said, "Derek Mitchell."  The name sounded familiar to me.  But my cheerleader knew right away.  "Derek?  Who played linebacker on our high school football team?"  Quarterback said, "Yes.  The same."  Cheerleader looked at him and asked, "But why?  Why bring other people into this?"  Quarterback shrugged, "Because I think it might be fun, and figured this was a better way to involve him and his girlfriend, than back home."  My cheerleader was quiet.  "So, what are you expecting?"  Then quarterback said, "Actually?  Nothing.  I expect nothing.  We could just have a good time with another couple.  Or, whatever.  Either way, they will never reveal what happens.  I am 100% sure of that.  But it is up to you and Sissy what else may happen.  It's completely up to you."  My cheerleader was quiet, still stroking quarterback's cock.  She asked me, "What do you think baby?  Will you be okay?"  Still not placing Derek, even though his name was familiar, I said, "I'll do whatever you want me to do.  You decide.  Please."  Cheerleader thought a minute or two and then said, "Well, they're coming no matter what, right?"  Quarterback nodded, "Yes.  They are.  They'll be here by lunchtime."  Cheerleader said, "Then I suppose we'll just have to see how things go.  Won't we?"  Quarterback smiled and then said, "I think it will be great.  You'll see."  Then to me, he said, "Mercedes is waiting for you Sissy.  She'll help you get ready for our company."  Dismissed, I went to my room to find Mercedes waiting for me as quarterback had said.
"So, are you ready?" She asked, as if she already knew what was going to happen.  "I suppose so," I told her.  "What shall I do?"  "First thing, go shower and shave all over.  You need to be nice and smooth and pretty.  I'll have your outfit waiting for you."  When I returned from my shower and shaving, I received my first clue about how Day Five would be spent by me.  Lying on the bed was a short, pink satin maid's uniform, complete with full white petticoats.  I stopped as I entered the room and asked, "Mercedes?  Do you know what is going on?"  She smiled her sweet smile.  "Yes Sissy.  Today you will serve Senor Tom, Senora Susan, and their guests, as their sissy maid.  I know you are familiar with this.  Yes?"   Mercedes had obviously been thoroughly briefed about me in advance.  What didn't she know about me?  "Yes.  I am familiar."  "Good then.  Let me help you."  She picked up a black lace garter belt from the bed and fastened it around my waist.  She then had me sit while she pulled a pair of black fishnet stockings up my legs and fastened them.  The stockings only came to mid-thigh, which made the straps extend far down my legs.  She then held up the petticoats and had me step in.  They were very short and flared out quite wide, leaving my chastity-caged clitty easily visible beneath the hemline.  She then helped me into a pink full cup bullet bra, and stuffed my large breast forms inside, resulting in a very prominent display of my breasts, as bullet bras are designed to do.  She helped me into the short pink maid's dress, the top of which was snug and form fitting around my bullet bra.  The result was a very sexy and, under the circumstances, embarrassing presentation of me to our guests as a first impression.  She kneeled and helped me step into my pink high heels, and then fastened my collar that said, "Sissy," around my neck.  She took me to the makeup table and began painting up my face in a very pretty way, before putting my wig on me.  Finally, as a sort of coup de grace, she fixed a headband with a lace bow on top, onto my head.  I was, to put it mildly, dressed as sissy as possible to meet quarterback and cheerleader's high school friend and his girlfriend.
I went out to the main room and found cheerleader and quarterback on the veranda.  They were each wearing bathing suits, and my cheerleader's was especially flattering to her figure, and did nothing to diminish her full breasts.  Understanding my role, I approached and did a full curtsy for them.  "May I do anything for you?" I asked in a soft voice.  Quarterback smiled.  "That's perfect Sissy.  Perfect!"  "Thank you sir?" I replied.  He told me to go help Mercedes and Maria in the kitchen.  We were going to serve lunch to our guests on the veranda when they arrived.  He told me that I was to greet them at the door.  I did as I was told and as I walked away I heard him say to my cheerleader, "Derek is going to love her!"
It wasn't long before I heard the Landcruiser pull into the driveway and then the doorbell rang.  I was beyond nervous.  I was about to meet a man who was a classmate of my cheerleader in high school.  I had no doubt that, if he didn't already know about me, and I suspected he did, that I would be introduced properly before long.  The moment I opened the door it hit me.  Derek Mitchell!  He wasn't just the linebacker on our high school team.  He was one of the best players on the team.  He played in college too.  And he was still built.  He was a big, muscular, black man.  And with him was a drop dead gorgeous blonde with very large breasts.  Standing behind them was the driver, who had their luggage.  I was, admittedly, struck dumb when I saw who our guests were.  They stood at the doorway taking me in as well.  Gathering my wits, I curtsied and said, "Welcome.  Won't you please come in?  I'll show you to Senor Tom and Senora Susan."  They greeted me and I could sense that Derek's girlfriend was enjoying the moment.  Like I said, I couldn't have looked sissier, and most of my movements caused my petticoats to reveal my chastity-caged clitty, over which, I believe I forgot to mention, I wore no panties.
I was hyper-conscious of the swishing sound my petticoats made as I led them out to the veranda.  I heard Derek's girlfriend whisper, "Oh fuck!  She's adorable!"  As I approached them quarterback and cheerleader came to greet Derek and his girlfriend.  Derek introduced her as Samantha, and quarterback introduced my cheerleader as her real name, although I'm going to use Susan in this post.  Derek knew her already, so there was no point in pretending.  They hugged and had some small talk about their trip.  Quarterback asked if they were hungry or wanted to freshen up after their flight.  Samantha said she'd love to freshen up and she wanted to change into a swimsuit too.  I wasn't sure which room they were going to stay in, so I looked to Mercedes for direction.  She walked with me and showed me that they were going to be in the bedroom on the other side of me.  As I left them I asked, "May I get either of you a drink?"  Derek said, "Yeah.  How about some champagne?  Y'all got any of that?"  I curtsied and said, "Yes sir.  We have pretty much anything you want."  Samantha giggled.  "I like the sound of that!"
I left them to change and went to the kitchen to help with lunch and to get them champagne.  I was setting up an ice bucket with their champagne when they rejoined quarterback and my cheerleader on the veranda.  Derek was wearing light colored swim trunks that he filled out nicely, and a tight fitting black tank top.  Samantha had put on a very sexy and revealing bikini that left virtually nothing to the imagination.  She was gorgeous and flat out built.  I filled four flutes with champagne and served each of them.  Quarterback toasted them with his trip slogan, "What happens in Mexico, stays in Mexico."  Everyone agreed and they clinked glasses before downing them quickly, which I promptly refilled.  Then quarterback said, "So, I don' know if you've been formally introduced yet, but," referring to me, "this is Leeanne, our sissy maid.  Actually, she's Susan's husband.  But I think you get what I mean.  She'll take care of any of your needs."  Derek and Samantha looked me up and down.  "Man!" Derek exclaimed.  "She's something else man!  Nice to meet you Leeanne.  Or can I call you Sissy?"  I blushed in embarrassment.  "However you wish to address me sir."  He actually kind of leered at me.  "Good then.  Sissy.  Nice to meet you."  Quarterback interjected, "Are you guys hungry?"  Samantha said, "Fucking famished!" And laughed.  I got the distinct impression that Samantha might be a party girl.  "Sissy," quarterback said, "Please attend to lunch.  We'll eat right over there," he said pointing to a table by the pool that looked over the ocean.  As I walked away I heard Samantha ask, "Do I get to play with her?"  Derek replied, "Be nice now.  We just got here."  But quarterback said, "Sissy will do as she is told."  Samantha repeated her earlier exclamation.  "I like the sound of that!"
I returned with lunch and served them.  They seemed to be enjoying each other's company and were definitely treating me as the servant, which actually made me feel more comfortable and useful.  After all, everything was out in the open at this point.  There was nothing for me to hide.  I decided the best thing to do was to tackle my role as their sissy maid with fervor.  Whenever I came around the table though, I couldn't hep but notice that Samantha was looking at my chastity-caged clitty.  As I was refilling their water glasses Samantha asked my cheerleader, "So, Susan?  If I may ask, how long have you locked your sissy in chastity?  She is so adorable in her little cage."  I know I turned beet red in that moment as she talked about me almost as if I wasn't there.  Cheerleader, not seeming put off by the question, replied, "Oh my!  It's been so long now I almost can't remember when she wasn't in chastity.  It isn't as if I need her to be released, if you know what I mean."  I was stunned to hear my cheerleader talk like that about me, even if true.  "I've heard it makes them more compliant," Samantha went on.  "Is that true?"  My cheerleader looked at me as I stood by the table awaiting requests for assistance.  "You know Samantha, I suppose.  But really, she has always been sweet and attentive to my needs, even before I knew she was a sissy and I accepted her as she is."  Then, Samantha leaned across the table, and whispered in a conspiratorial tone, although I could hear her, "Do you mind?  May I touch it?  You know, her thingy?"  I was about to freak out.  This was more than I'd primed myself for.  I looked at my cheerleader, who smiled up at me as she spoke.  "I don't call it a 'thingy.'  I call it a clitty.  And yes, you may touch it.  Sissy?  Would you come over here?" She directed me.  Oh fuck!  My cheerleader seemed to be all in.  Obediently, I walked over to Samantha and stood by her.  She grinned up at me as she only slightly lifted my petticoats, exposing my caged clitty for everyone to inspect.  And believe me, all eyes were on me, even Mercedes and Maria from across the room.  Then she reached under my skirt and touched me, softly, delicately, and tenderly.  "Oh my!  She's so soft and smooth.  I love that you shave her too!  So cute!  Isn't she adorable Derek?"  Derek laughed.  "Yeah.  She's adorable alright.  Man!  This is a trip!"  I felt so humiliated and embarrassed as I stood there being fondled and inspected by this beautiful and luscious blonde, but the truth?  I was loving every second of it.  I felt safe.  And I knew that I may never have another opportunity like this again.  I decided then that I was going to do whatever anyone wanted for the rest of the trip.  When Samantha seemed to have satisfied her curiosity, she removed her hand and I did what any self-respecting sissy maid would do.  I did a deep curtsy for her and said, "Thank you ma'am."  Samantha about went ballistic at that.  "Oh fuck!  So fucking cute!  I love her Susan!  Love her!"  Cheerleader smiled, almost proudly?  "Yes.  She is quite the adorable one."  Quarterback then jumped in, "Sissy.  Please clear the dishes and go clean up.  Leave us for a while to relax.  We'll let you know if we need anything."
I left them and went to the kitchen to help clean up.  Mercedes and Maria already had things under control.  Mercedes told me to relax while they finished up.  I could feel she'd seen what had just happened and felt sorry for me.  Little did she know how much what Samantha had done turned me on.  Little did she know how much I was fantasizing about tasting her pussy.  Suddenly I heard a loud splash.  I looked toward the pool and sure enough, as I had immediately suspected, Samantha was in the pool.  She shouted to my cheerleader, "Come on in Susan!  It feels great."  They were all having fun with each other.  I saw quarterback nudge my cheerleader, encouraging her to jump in too.  She seemed reluctant, but she stood up and then ran and jumped in, causing a big splash as Samantha and she both began laughing together in the pool.  My cheerleader began trying to coax her quarterback to jump in and within seconds, he and Derek were in the pool with their women, the women draping themselves all over the men.  Quarterback looked over toward me in the villa and called out, "Hey Sissy!  Bring us some beer!"  Mercedes helped me load up a tray with four cold beers and I carried them out to the side of the pool.  When I arrived, the four of them were horse playing together in the pool, the screeching sounds of the women loudest of all.  For the moment, I was ignored as I stood by with their beers, and wasn't sure what to do, so I just stood there watching them.  Samantha was all over Derek, and was suddenly kissing him as she wrapped her white legs around his dark body.  She was definitely a party girl.  Then, in a quick motion, she had untied her bikini top and let it go and suddenly it was floating on top of the water and her full breasts were exposed for everyone to see as she pressed them against Derek and kissed him in a full and long kiss.  When she stopped kissing him, she yelled at my cheerleader, "Come on Susan!  What are you waiting for?  Lose the fucking top!"  In a blink my cheerleader made her decision.  What happens in Mexico, stays in Mexico.  She untied her top and tossed it over to the side of the pool by my feet.  I was, in short order, a spectator to my cheerleader and Samantha throwing themselves,, half naked, at their men.  She then dove at her quarterback and grabbed him around his neck, taking him into a full embrace and began kissing him too.  Samantha was definitely leading the charge in creating the play time in the pool, but my cheerleader very quickly got into the swing of things as well.  Samantha climbed up onto Derek's shoulders and challenged my cheerleader and her quarterback to a game of chicken.  Before I knew it, my cheerleader was on her quarterback's shoulders and the four of them began sparring with each other in the shallow end of the pool, both women's bare breasts swinging freely and and on full display.  It was, without a doubt, a very erotic display.  As the two women grabbed at each other, both naked, I sensed that Samantha was up to something.  After a few minutes of grabbing and touching each other as each tried to knock the other off of their respective man's shoulders, Samantha grabbed my cheerleader around her neck and pulled her and quarterback right up to her and Derek.  The next thing I knew, Samantha was kissing my cheerleader and my cheerleader wasn't resisting.  No, to the contrary, she was kissing back, all while quarterback and Derek watched and seemed to be in no mood to stop them. 
Without warning, but as if choreographed, Derek and quarterback tilted into the pool, dislodging their women from their shoulders.  Instead of letting go of my cheerleader, though, Samantha went at her even more ferociously, kissing her deeply, wrapping her legs around my cheerleader, their plump breasts pressing against each other.  I was confident that my cheerleader had never been with a woman before, although I was equally certain that Samantha had been.  She knew what she was doing.  They broke their kiss long enough for Samantha to laugh out loud and then she broke away and swam over by the steps.  My cheerleader, now into the game, gave chase.  Samantha wasn't really trying to get away though.  I think she was only trying to lure my cheerleader to a shallower part of the pool.  Just as my cheerleader caught her, Samantha quickly turned and grabbed around my cheerleader's neck again, pulling her closer and locking onto her mouth again.  In a deft move that must have been done many times before, Samantha had removed her bikini bottoms and reached down to untie my cheerleader's, who offered no resistance.  Now both of them were naked in the pool.  Samantha began edging my cheerleader toward the top step of the pool and soon had her sitting there, with Samantha between her thighs, and the next thing I knew my cheerleader's legs were draped over Samantha's shoulders and Samantha had her mouth locked onto my cheerleader's pussy, who was screeching her obvious pleasure to have a woman eating her pussy.  Now that she had my cheerleader in the position she was in, Samantha did not show any signs of letting her escape, not that my cheerleader showed any designs to attempt to do so.  Soon my cheerleader was letting loose with an uncontrolled orgasm as Samantha was devouring her pussy.  When she was finished, my cheerleader was looking at Samantha like, 'What have you done?'  She pulled Samantha up to her and began kissing her deeply as a show of appreciation.  By then, quarterback and Derek had come over to where I was standing by watching to retrieve their beers.  When the women were through, they came over too and took their beers from me.  My cheerleader looked at me like, 'Did you like that?'  I just curtsied and asked if they needed anything else.  Samantha looked at my cheerleader and asked, "What about her?  Can she lick a pussy?"  My cheerleader laughed.  "Can she?!  It's what she's best at."  "Oh really!" Samantha cried.  "Then yes Sissy, there is something I need."  She pulled herself up from the pool and walked over to one of the chaise lounges and laid back on it.  "Come Sissy.  Show me what you got!"  I looked at my cheerleader, who nodded.  "Go on Sissy.  Take good care of her."  And so, as everyone watched me, I got onto my knees and had my earlier wish fulfilled.  I did her as good as I've ever done anyone and when I finished, she exclaimed.  "Oh fuck me!  I need a Sissy!"  Everyone laughed as I smiled that she was so satisfied. 
The rest of the afternoon was relatively quiet, with the four of them hanging by the pool.  I had to bring beers to the guys a few more times, and the naked women were all over their men.  Then, they went to their rooms to shower to dress for dinner.  The first person to come out for dinner was quarterback.  He came into the kitchen and walked up to me.  “How are you Sissy?”  I curtsied and replied, “I’m fine sir.  May I get you a drink?”  He smiled.  “You are doing so well Sissy.  Yes.  You may.  And Sissy?”  I paused and answered, “Yes sir?”  “Thank you.”  I wasn’t certain why he was thanking me, but replied, “You’re welcome sir.”  I curtsied and then went to make his drink.  Soon after my cheerleader came out.  She looked hot!  She was wearing a very short and tight fitting lycra red dress, cut very low in front, with black heels.  She looked stunning.  She walked into the kitchen, came up behind me and kissed me on my neck.  “Hi baby,” she whispered.  “How do I look?”  I smiled.  “Totally hot!”  She sighed.  “That’s the idea.  I want my man’s cock hard all night.”  I poured her a glass of white wine and she went out on the veranda to join her quarterback.  When she reached him she snuggled up behind him and he pulled her to him and gave her a long passionate kiss as his hands fondled her tight ass possessively.  A few minutes later Samantha and Derek came out together.  Samantha was wearing an ultra short white skirt and a sheer black blouse through which a white lace bra was visible.  Her boobs were virtually exploding out of the top of her bra.  I approached them, curtsied, and then asked if they would like a drink.  After taking their orders they joined my cheerleader and quarterback on the veranda.  When I delivered their drinks to them, quarterback and Derek had moved to the edge of the veranda and were talking as they looked out at the ocean.  Cheerleader and Samantha were chatting together.  I took Derek’s drink to him and then approached the two women.  When I walked up to give Samantha her wine, she put her hand up, signaling for me to wait.  She reached up to brush a stray strand of hair out of my cheerleader’s eye, a very intimate act as it unfolded.  Then, in that same instant, she leaned in and kissed my cheerleader on her mouth.  While I stood by holding her wine, Samantha said to my cheerleader, “Do you know that you have the sweetest cunt I’ve ever tasted?”  My cheerleader actually blushed.  “No,” she answered with a nervous laugh.  “I didn’t know that.”  As she gazed into my cheerleader’s eyes, Samantha reached under my cheerleader’s dress and I could tell she was fingering my cheerleader’s pussy.  “Oh my!” she exclaimed.  “What have we here?  Are you wet Susan?”  My cheerleader sighed and said, “Maybe.”  Samantha withdrew her fingers and tasted them.  “Mmmm.  Such a sweet cunt.”  She stuck her fingers in my cheerleader’s mouth and asked, “Don’t you think?”  My cheerleader was enthralled at her new friend.  Samantha placed her hand back under my cheerleader’s dress and this time I could tell that she was fingering my cheerleader intently, interspersed with soft wet kisses on her mouth.  “Have you ever tasted another woman’s cunt Susan?” she asked.  “I don’t think you have.”  My cheerleader shook her head and, in a barely audible voice, said, “No.  I haven’t.”  Samantha gave her a sly grin.  “Want to?”  Still responding to being fingered by Samantha, my cheerleader answered, “I think so.”  Samantha removed her hand from under my cheerleader’s dress, put it in my cheerleader’s mouth and let her suck it.  When she removed her fingers from my cheerleader’s mouth, she placed her hands on my cheerleader’s shoulders and gently, but firmly, pushed downward as she said, “There’s no time like the present.”  The recognition in my cheerleader’s eyes at what Samantha was suggesting only lasted a moment as she allowed herself to be pushed down to her knees in front of Samantha.  Samantha pulled her skirt up revealing a matching pair of white lace panties, which she pulled to the side and then pulled my cheerleader’s mouth toward her.  As for me, I was mesmerized at what I was witnessing.  “Do you smell how aroused you have made me Susan?  That’s all because of you.  Go on.  Taste me.  Take your time.  It’s yours.”  With one hand behind my cheerleader’s head, Samantha gently guided her mouth closer to her pussy and sighed as my cheerleader began to lick and then kiss her wet, smoothly shaved pussy.  She slowly searched her way around Samantha’s pussy as she seemed to enjoy the response to her oral pleasuring.  Samantha moaned, “Oh yes!  Susan!  Yes!  Suck my cunt baby!  Go on!  Suck it hard!  I’m going to cum in your mouth.  It’s coming!  It’s coming!”  She grabbed my cheerleader by the back of her head and pulled her firmly against her pussy and began bucking into my cheerleader’s face.  As for my cheerleader, she was groaning and moaning as she sucked Samantha harder and harder.  “Oh fuck!” Samantha cried out.  “That was so fucking good Susan!  So good!”  She then helped my cheerleader stand up and kissed her hard on her mouth.  Then, in an understated casual manner, she reached over and took her glass from me.  “Thank you Sissy.”  I was left standing there, in an awkward moment, as the two women continued to kiss each other after my cheerleader’s first time ever eating out another woman.  Finally, my cheerleader said to me, “You can go now Sissy.  Leave us alone for a few.”  I curtsied and said, “Yes ma’am,” and turned to walk back to the kitchen.  As I walked away I heard Samantha say, “I need to take you to bed and fuck you Susan.  Soon.”  My cheerleader didn’t hesitate.  “I think I’d like that.”
After a while I served them dinner and stood by to bring wine and anything else they wanted.  By this time my feet were sore from walking in my high heels all day.  It really had been a long day of work for me.  I continued to serve them until it was late and they all retired to their rooms on either side of mine.  The last thing I will recount about Day Five is what I heard from my new neighbors.  After they went to bed, the never sexually satisfied Samantha went after Derek.  And he must have been something.  She was crying out his name, encouraging him to fuck her harder and telling him how much she loved his big cock.  I wondered whether my cheerleader and her quarterback could hear them in their room separated by mine.  In any event, the day had been pretty amazing, all in all, and I wondered what quarterback had in store for me and my cheerleader the next day.