Letting Go

Once her virginity was taken from her, sissy quickly learned how to open up and enjoy being taken by her wife’s boyfriends.

Night Life

Sissy had been on the wall for almost two hours behind the night club she and her wife frequented.  She’d lost cunt of the number of men she had serviced, but there was no questioning that she was earning her keep.

Foreplay

Sissy’s new boss liked how her lips felt on his cock, but he enjoyed the foreplay more...

Private Lessons

Sissy receives hands on instruction from her wife...

The Bathroom Choice Dilemma

The girls’ room at The Vera Wang Institute for Male Modification, a/k/a “Sissy School.”  Who uses the boys’ room you ask?  Giggles.  There is no boys’ room!

Submission

If he has his way (and he will), sissy will be taking care of his cock and balls for quite a while.  And sissy won’t be complaining either.

Not Even Close

Sissy never made her wife quiver like this.

Don't Think Sissy. Suck.

Real Man versus Former Man

As if sissy needed any more proof of her weakness in the company of her wife’s boyfriend, when he did this to her the first time, sissy understood that any remaining vestige of her manhood had all but evaporated...

She Likes To Watch

When sissy’s wife allows sissy her one minute of release for the month and then watches as sissy desperately attempts to finish within her allotted time.

It's Different For Men

Sissy learned time and again that there were things her wife would do with the men she brought home that she would never do with sissy.

The Mouth Gag Preferred By Most Sissies

At least it's my fav.

Sissy's Wedding Night

Sissy’s wedding night isn’t turning out exactly as she’d expected.  To begin with, her wife set the ground rules for their marriage right away, inviting her boyfriend along for their honeymoon.  Now, instead of sissy consummating her marriage, she’s fluffing her wife’s boyfriend, who’ll handle the honors of consummating the marriage.

Panty SelectionMatters

Sissy now understood why her wife had discouraged her not wearing the full cut panties with this particular skirt…

Just Sayin'

When a wife introduces her sissy husband to her new boyfriend for the very first time.  All concern of competition are wiped away.

There Is A First Time For Everything

And sissy likes it.

The New School Year

Lee, always a discipline problem at school and at home, had been away visiting his aunt for the past year.  Now Leeanne, her first day at school for her junior year promised to be different, not least of which was the new school uniform she would be wearing instead of khaki pants, shirt and tie.  She might even try out for the Cheer squad.  

First Date

Sissy’s wife went on a date with a new guy at her office.  When he found out that her husband was a sissy and knew about their date, he thought it would be considerate to share a video of their first date.

Orientation

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

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.”

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.

Sissy Loves Opening Presents

Waste Not - Want Not

The "Win-Win-Win" Position

At least, that's what sissy, her wife, and her boyfriend call it.

The Ultimate Fluff

What sissy does to help her wife's boss get ready for her.

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.

I. Love. Cock.

There is nothing that feels better between my sissy lips than a nice, big cock.

Sissy's Safe Place

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!!!!!!”

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.”

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 Isn’t 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.