A Stimulating Conversation Between Old Friends

Sheila sat down at an outside table sipping a cup of cappuccino.  It was a beautiful spring day, and she had just gotten her long brown hair and nails done at the beauty salon.  It was a day to treat herself, and she wanted to look good.  She wore a blue dress that went down to her knees and three inch heels.

This wasn't a date with her boyfriend.  In fact, she had grown frustrated with her boyfriend of four years.  This was bad news, because the two were headed to the alter in June.  She loved him, but she felt their relationship had grown stale.  It frustrated her, and she didn't know what to do about it.

She was looking forward to meeting her old friend from high school, Amanda.  Amanda had a wild streak back in those days.  She loved to party, and Sheila usually followed her lead.  The two always had a fun time together and somehow managed to stay out of trouble.  It was a sad day when Amanda left the state to go to college.

That was almost ten years ago.  She still pictured her friend with long black hair, a gorgeous figure that she envied, and ample bussoms.  The fact was she had feelings for her old friend, and the two had a bit of a fling together.

She watched as a lady dressed in tight jeans and an equally tight top came walking down the street.  This lady had short black hair, and it took Sheila a moment to realize that this was her dear friend.  She stood up to greet her.  "Amanda, so good to see you."

"Oh my God.  Sheila, look at you.  You look amazing, " she said as she hugged her tightly.

"Me, look at you.  My God, still gorgeous and an amazing figure."

Amanda sat down.  "Oh please.  You're a hottie."

Sheila smiled and blushed just a little.  "So, what are you up to these days?  What's it been, ten years?"

Amanda didn't answer at first.  The fact was she was now a professional and lifestyle dominatrix.  She made good money doing it and also operated an extensive web empire.  This allowed her to travel all over the world.  "Well, I'm sort of a Jill of all trades.  I council businessmen over the stresses of work.  I have an internet business.   You know, this and that."

"Oh, so the psychology degree paid off?  Good for you."  A lady brought a cup of black coffee to the table.  "Oh, I took the liberty of ordering you a cup of coffee, it's black..."

"Like my men, " she interrupted as the two laughed.

It got silent for a moment as Sheila admired her friend's necklace and earrings.  They were gold with diamonds and looked quite expensive.  "Look at you, the successful business woman."

"Oh stop it, " she interrupted.  "I know about you opening that second clothing store.  And you're getting married too?"

Sheila forced a smile.  "Yeah, married.  Oh, I was gonna ask you if you wanted to be my matron of honor."

"Of course I will, " she replied as she took her friend's hand, "but there's something you need to tell me first."

"What's that?"

Amanda shook her head.  "Don't even try that.  You know I can see right through you.  What's the problem?"

Sheila nervously sipped her cappuccino.  "It's nothing.  It's just that things have gotten a little, I don't know, stale with Bill and I."

Amanda grinned devilishly, and Sheila knew that look well.  "What is it?  What are you thinking?"

She decided to come clean about her career.  "I know exactly what would help you get the most attentive little sissy hubby you could ever want."

Sheila laughed.  "What are you talking about?"

"Sweetie, I'm a Pro Domme.  I have a stable of subs, and some of them are cute little feminized sissies, like my husband, " she took a sip.  "Or I should say wife, since she is dressed 24/7 and in chastity."

Sheila's face went red.  "Chastity?  Your husband?  Don't you love him?"

Amanda lit a cigarette.  "You've got it all wrong, dear.  She loves her role as my wife, keeping things in order at home for me, making sure I have what I need to start my day and..."

"Wait, he actually likes it?"

"Well, it was a process, but I broke the little sissy down fast.  She does what I say and doesn't have an orgasm unless I tell her she can.  I plug her sometimes.  She sleeps in another bed in my bedroom unless I give her permission to share my bed.  She serves my boyfriends and me when she's told, and like I said, she's locked 24/7.  In fact, sometime I tie her up or spank her, or both, when she needs it."

Sheilas jaw dropped.  "I don't believe it."

Amanda reached for her purse.  She produced a picture of a man and another of somebody who looked like a woman, almost passable, with long blonde hair, and a pink dress."

"And that's..."

"My sissy wife Emily.  She really is adorable, " she beamed.  "You have to meet her."

"Why are you dong these things to somebody you love?"

She took another sip of her coffee.,  "It's exactly because I love her that I do it, because she needed it.  She didn't realize it at first, but she came to accept it.  She's a devoted little sissy, and she makes my life a lot easier.  She's really quite smart too."

Sheila was just staring at her friend.  "But, your sticking...."

"Plugs, sometimes dildos or my lover's cocks or..."

"Inside her and and using...  Chastity on her, um, him?"

Amanda grinned.  "Yes, I am."

"Why?"

Amanda had studied the BDSM lifestyle and read many books. especially on female domination.  "Well, sweetie, you use chastity to make your sub stop thinking with his little head.  Once he accepts that he's not getting inside you, you find out how much he really loves you.  How much he's willing to please you in other ways, and not just sexually.  In fact, she craves being locked up."

"But why the strap on, " Sheila asked, shocked at what she was hearing from her friend?  She had a wild streak, but this was much more than she remembered.

Amanda put out her cigarette on the ground.  "Because, after I've taken away his manhood, I establish my role as dominant by making him service my strap on orally.  And fucking her lets her know her position in our household.  The little sissy slut starts craving it."

"But bringing other guys into the bedroom."

Amanda grinned.  "Well, you know how much I love big cock, and she was average at best.  I love her for other reasons.  But, I still need a good fucking from time to time, and she loves seeing me pleased that way.  Of course, I could see she was a bit jealous of the cock, so I let her get in on the action when I think she's deserving.  Or, I'll arrange something for her in a more public setting."

Sheila could hardly believe what she was hearing or that she was turned on by it.  "And she likes that?"

Amanda shook her head.  "No, she loves it.  She's a little slut."

"So, she's gay then?"

Amanda finished her coffee.  "Oh no, she's bi.  She would fuck me in an instant if I let her.  I like to tease her and put her caged clitty up against my pussy and ask her why she's not fucking me.  Then she eats me out.  Oh, Sheila, she is a pro.  She can go for as long as I need her to, and she's very thorough."

Sheila's panties were getting wet at the excitement.  She couldn't deny her interest in this.  "How did you manage to do this?"

The Pro Domme couldn't erase the proud grin from her face.  "Why, are you interested in having a sissy of your own?"

Sheila shifted uneasily in her chair, but she couldn't deny her interest.  "I'd just like to hear how.  I don't know if I could make..."

"That's what they all say, " she interrupted, "but I know better.  Most men have an inner sissy waiting to get out.  Your Bill is no different.  You'll have Billie the sissy house wife in no time if you listen to me."

Amanda watched her friend as she shifted in her seat.  She could tell she was aroused.  "Oh my God, did you just get your rocks off?"

Sheila blushed.  "No"

"You little liar, " Amanda replied as her cell phone rang.  "What is it sweetie? Mama's busy."

Sheila looked at her friend in amazement.  Would it be possible to feminize Bill into a sissy husband?  Could she do such a thing?  She would love having an assistant as she grew her own business, and she couldn't deny how turned on she was.

Amanda put down the phone and grabbed a business card and a pen.  "Listen, sweetie, I've got a client I need to deal with.  A real high roller.  Loves to be tied up and spanked, and I'm in just the right mood."

Sheila chuckled.  "They pay you for that?"

"Oh yes, five figures a month with this one, " she wrote down her hotel information.  "Tomorrow, come by my room at say, noon for lunch.  My sissy will be there to wait on us, and we can talk about it.  I'm really sorry. I have to go now.  I hate cutting this short, " she hugged her friend and kissed her on the cheek.  "Please come by.  No pressure.  I just want to show you what is possible."

Sheila watched as her friend walked away, admiring her shapely ass in those tight jeans.  She decided right then and there that she was gonna meet her and see what she had to say.  It could be interesting at least.  Whether she could go through with anything or not was another question, but she was open to the possibility.

Old Friends Meet As Sissies

Sissy Nicole sat at one of the tables outside the coffee house, sipping on a latte as she browsed the Internet on her laptop.  It wasn't easy for her to take these steps by herself.  She learned fashion and makeup and gained confidence all on her own.

She recalled the days in the chat room among other would be sissies.  They lived their fantasy in a chat room.  Nicole didn't want that life.  She had spent too many years as it was living this life inside her head.  She wanted to just be.

So, one day she took the plunge and just started teaching herself.  She shopped alone, practiced makeup and was eventually living life as a woman 24/7.  Not exactly passable, but presentable.  She wasn't afraid to go out the way she did.

Today it was a red dress and matching heals and hand bag.  To complete the look, he wore red nails and lipstick.  She was feeling good about herself.  She looked in the mirror before she left, and she loved the sexy woman staring back at her.  "I'm getting there, " she thought, as she finished brushing her long brown hair.

Vanessa came walking by the coffee house and did a double take.  Was that Nick?  Dressed as a woman?  She knew Nick in High School.  That is to say, they were friends.  She didn't go by Vanessa then as she hadn't come to terms with herself then.  She had yet to begin transition.

She walked up to the sissy who was focusing on the screen, oblivious to the world around her.  "Excuse me, do I know you?"

Nicole looked up from the screen.  The face looked familiar, but she couldn't place it.  "Maybe.  Let me think."

Vanessa noticed her friend's voice wasn't quite right yet.  "No, I'm sure of it.  We used to go to high school together.  We used to hang out."

The image of her old friend David came to mind.  "Oh, yeah.  You're Da...  Wait, what is your name now?"

Vanessa smiled and pulled up a chair at the table.  "I'm Vanessa, and what's your name.  Nicky?"

"It's Nicole. but you can call me Nicky if you want."

Vanessa eyed her friend.  "Oh my God, I had no idea you were trans.  You look good girl."

Nicole laughed.  "Me?  Look at you girl.  You look amazing.  Wow."

"Well, I didn't used to.  My Mistress helped me out.  Taught me a lot of things I needed to learn."

"Really?  I've heard a Mistress can be cruel."

Vanessa laughed.  "Oh, well sometimes I needed to be disciplined.  She locked me up in chastity..."

"Chastity!  Oh my god."

Vanessa reached across the table and touched her friend's hand.  "Oh, it's not that bad.  I was scared at first, but she showed me that I needed to lock it up to help me bring out my femininity."

Nicole still looked unsure.  "But, doesn't it hurt?  I mean..."

"No silly.  It's not that bad, and it has kept it from being a nuisance for me.  Well, I'm on hormones now, so it's not an issue, but I keep it locked up.  It makes Her happy.  I love my Mistress, and I do what it takes to make Her happy."

"Well, I've never met a woman who wanted anything to do with me..."

Nicole brushed her brown hair from her eye.  "I was in the same boat, but I met Mistress at a club.  She taught me so much.  I live with her and clean house, tend to her needs.  We're together, but she still has boy friends and..."

"Boyfriends?  I don't know about that..."

Vanessa took out a mirror and freshened up her lipstick.  "It's not that bad.  I mean, I can't expect her to be happy with a limp clittied little sissy, but I get to satisfy her in other ways.  Plus, sometimes she brings guys back for me and...?"

Nicole gasped.  "Guys?  I don't know about that, and I don't know if..."

Vanessa smiled.  "I do it for her.  I'm not really looking for a boyfriend, but I've sucked cock for her and more when she's asked me to.  She doesn't have a boyfriend as such, but she has guys over when she wants them.  She's a Pro Domme, and sometimes she uses me in a session if..."

"A session..."

Vanessa reached into her purse. "Look, sweetie, I'd love to fill you in on everything.  I think you'd be interested, but I have errands to run for Mistress.  I need to get going.  Let me give you my number."

Nicole shook her head.  "I don't know if I'm up to all of that..."

"Nonsense, " she said as she handed her a piece of paper with her number and address.  "You just don't know and you're scared.  I understand.  We can just talk and I can give you a tour of the dungeon..."

"Dungeon, " she interrupted as her face went white.  "There's a dungeon?"

"She's a Mistress, silly.  Of course she has a dungeon.  You just have to see it.  Say you'll come visit."

"I guess so."

"Great."  Vanessa got up and gave her friend a hug  "You'll love it.  Don't worry.  It's just a visit.  Maybe you can meet my Mistress too."

"Okay, maybe I will."

"Are you free Friday?"

Nicole thought for a moment.  "Yes, I am."

"Good, I'll see you then."  Vanessa walked away with a smile.  Nicole had potential to be the new sissy her Mistress was looking for.  It might take a little work, but she believed she could get her.  Nicole would be uncomfortable at first, she reasoned, but would learn to love it just as she did. 

A Poem: Lock Me In Chastity

Lock me away in chastity
It is for my own good
I'm such a naughty sissy
If I could submit I would



I know I may sound silly
And perhaps a little dumb
I hate to make a sticky mess
I hate it when I cum



For months now I've denied myself
I won't go all the way
But still I like to edge myself
I figure that's okay



My panties tent from time to time
When naughty thoughts come by
I do get horny I'll admit
I have no cause to lie



I must confess to you right now
And it may be a pity
Though it may give me pleasure
I still wish I had no clitty



I know that it's not good enough
So I must set the stage
And lock my clitty nice and tight
Behind a metal cage



That simply isn't good enough
It can't be up to me
To make sure that it's now controlled
I cannot hold the key



My clitty I can rub no more
And I can truly see
The panties will not hide the fact
That I wear chastity



Though I may beg and I may plea
I must not have a choice
I must obey your harsh response
And know that you'll rejoice



My clitty now belongs to you
And it's as good as locked
Though I may beg and I may plea
I am as good as blocked



You laugh at me and ask me
"Why is it that you're so dumb
There is but one way for you now
If you so need to cum



Just take your toy out of it's box
Don't let desire pass
Lube up your dildo really well
And shove it up your ass



And work it in there like you can
You're such a sissy slut
I know that you can do it well
The pleasure's in your butt"



That is the way it is for me
You tell me here and now
For I must ride my dildo well
You tell me I know how



That is the only way for me
My clitty's owned by you
And If I really want to release
My dildo has to do



Perhaps there is another way
You say with your sweet smile
All that I'll get from you now
Is more tease and denial



But if I really want to cum
You tell me there's a plan
Dress up just like a sissy slut
And find and please a man



Embrace the sissy that I am
And then I'll have more luck
Offer up my sissy hole
For his big cock to fuck



Learn to work it well inside
And try not to play dumb
'Cause if I do it well enough
Then he and I will cum



Desperately I beg you now
Is there some other way
May I serve you with my tongue
I tell you I'm not gay




But you just laugh and say to me
I don't deserve the chance
You do not want to hear my crap
So no more song and dance



A sissy fag is what I am
Or all that you will see
And I now need to understand
It's what I'm meant to be



It was not you who asked me then
To lock away my clit
I was the one who made my bed
Now I must lie in it



You tell me now that I can squirm
And that does bring you pleasure
The key to my release right now
You carry like a treasure



All I can do is beg you now
You love to laugh and tease
And that is now the only way
For you that I can please



I can no longer edge myself
And it will stay that way
The only pleasure I may have
Will come from being gay

Jennifer's First Boyfriend

Jennifer walked into the restaurant in a blue dress and heels.  She let her long brown hair flow, gently brushing some hair from her eyes and revealing her long fingernails that she had painted in a red heart design.

She was nervous.  She hadn't seen Billy in nearly ten years.  What if he didn't like what he saw?  When she last saw him, her name was John, and she was a freshman in high school.  Billy was nearly two years older and was her next door neighbor.

She saw him at the table, short black hair and a neatly trimmed beard, and his blue eyes.  She could never forget his eyes and how they looked at her.  They were looking at her now as a smile came to his face.

He stood up to greet her.  "Jennifer.  My God, it's so good to see you again.  You look so beautiful."

She smiled at him as he held out her chair for her.  "Thank you, Bill.  You look handsome, by the way.  How are the wife and kids?"

He sat down.  "Oh, Linda is doing fine.  She had to work late, but she sends her regards  She's hoping we can all get together tomorrow.  The twins are growing like weeds.  How about you?  Weren't you dating a motel owner?"

She frowned.  "We broke up."

"I'm so sorry to hear that."

She took a sip of water, leaving a mark of her red lipstick on it.  "Don't be. I wanted more than he did.  It's better this way."

"Well you're a sweetheart, Jennifer.  You always were.  You deserve happiness."

They ordered their meals and enjoyed small talk, but their minds were going back to a time when they shared something very special together.  A time when Jennifer came to be.

Bill's mind was racing through the memories of those days.  Though he hated to admit it, he was aroused thinking about those days. "I was just thinking about the time you walked out in your sister's old red babydoll.  Remember that?"

She blushed.  "What about the time you stole Lisa Miller's cheerleader's outfit and gave it to me?"

He laughed.  "It looked better on you."



Billy and John sat on a couch.  John was home alone, so he invited the older boy over to watch porn with him again.  He had a video of women giving blow jobs that got them both excited.  Usually, they ended up masturbating together when they did this.

Billy was 14 and John was going on 13 and about to graduate junior high.  Billy was looking at the brunette deep throating the man's big cock.  "You see, that's what I'd like right there.  A nice deep blow job.  Fuck, that's hot."

Billy was rubbing his shorts.  As John admired the woman in the pretty pink lingerie.  "God, she looks so hot in that pink nightie.  I bet it's conformable too."

Billy looked a his younger friend.  "What do you mean?"

He blushed.  "Oh, nothing.  Its just that I think she's sexy.  Have you ever had a woman do that to you?"

The older boy shook his head.  "Not yet.  I wish.  The girls at school are so stuck up."

What was going through John's head now was something he'd thought of many times as he would rub himself in the panties he would steal from his mother or sister.  He'd seen his friend's six inch cock and the pubic hair, so manly compared to his.

He fantasized many times about sucking his friend's cock and being like one of the women in the video, dressed pretty.  He had a slender and almost feminine body, but he knew that might change as the effects of puberty really took hold.

He was nervous, but he wanted to try what was on his mind.  "Billy, I want to show you something.  If I do, you have to promise not to laugh."

The teenager laughed.  "Dude, how long have you known me?  Have I ever been mean to you?  You don't have to say that, just show me."

John nervously smiled and stood up and went to his room.  He had a stash of a few bras and panties and other things that had been discarded by his sister because she got new things.  He reached for a white lace bra and satin white panties and put them on.

He looked in the mirror, and his small three inch penis was hard as it tended his panties.  He put on a red babydoll nightie and admired himself in the mirror as he brushed his medium length brown hair to try and make it look more feminine,  "Are you okay back there, " he heard Billy ask?

"Just a minute, " he shouted back as he reached into the bottom drawer of his dresser in the back for a tube of red lipstick his sister thought she lost.  He slowly applied it to his lips, being careful to get it just right.

He smacked his lips together.  "Here goes nothing."

When he entered the living room, Billy stared at him with his mouth open, but he didn't say a word.  John was so nervous, he thought he would pass out,  "Well, what do you think?  I could go back and change if you want me to."

Billy kept looking at him and began to smile., "Don't you dare.  You look great. Sit down with me  How long have you been doing this, John?  Or what do I call you?"

"About two years now, " he explained.  "It started when I found a pair of my sister's panties in the bathroom and tried them on.  I wear panties most of the time now.  And, I like the name Jennifer."

The teenager nodded.  "Jennifer it is.  Do you mind if I pull my pants down, Jennifer?  I feel like I'm gonna explode."

John  smiled.  "Not at all.  You were gonna do it anyway."

Billy's cock stood straight up and he looked at his younger friend.  "So, do you think about sucking a cock like the ladies in the video?"

"All the time, " he admitted.  "I know I shouldn't, but I feel like I should be a woman, and..."

"It's okay Jeniffer.  It's natural for a woman to want to suck the cock of a man.  In fact, if you want to...   No, forget I said that."

John licked his red lips.  "No, I want to, if you want me to.  I don't want you to be creeped out."

Billy shook his head.  "Jenn, I like you a lot.  You know that.  If you want to do this for me, you can.  I won't tell anybody.  It'll be our, "John went down on his friend before he completed the sentence.  "Secret.  Oh, God.  This is really happening.  Wow.'

John tried to emulate what he'd seen in the videos with the women, humming as he sucked his friend's cock.  He could taste something he had never tasted before, kind of bitter, but not unpleasant.  He kept sucking and suddenly Billy tensed up and erupted his seed inside his friend's mouth.  John swallowed it all and kept sucking until he began to go limp.

Billy looked over at John and smiled.  "That was amazing, " he kissed him.  "Thank you, Jennifer."



The scene kept being repeated whenever they could do it, and sometimes Jennifer was in full makeup as she was learning how to do it.  They would do it in her dad's car, at Billy's house or under the high school bleachers wherever they could.  They had pretty much become boyfriend and girlfriend and spent a lot of time together.

It was under the bleachers on a Saturday afternoon where Jennifer was waiting for Billy.  She wore a pair of shorts that used to belong to her sister and a pink top she actually bought at the store.  She pulled out a mirror and did her makeup as she waited.  Billy had something in mind, but he didn't say what.

No sooner had she finished her makeup than Billy approached with a bag.  He kissed his younger feminine friend.  "Hi babe.  Did you miss me?"

Jennifer hugged him and pulled him in for a deeper kiss.  "Does that answer your question?"

Billy handed her the bag.  "I brought something for you."

She grabbed it.  "What is it?"

He smiled.  "Just look.  I know you're gonna love it."

She opened the bag to reveal a black, pink and white skirt and top with the school logo and team's name on it.  She gasped.  "A cheerleader's outfit?  How?  Where did you get this, Billy?"

"I, um, I sort of borrowed it from Lisa..."

"Lisa Miller, " she exclaimed?  "The head cheerleader?"

"Well, I know you want to be a cheerleader.  I don't know if it will happen, but I thought maybe I could give you the next best thing.  Put it on for me."

"Billy, we've got to take this back to her.  It's not right."

He grinned.  "We'll talk about that later.  Just put it on.  I want to see you in it.  I bet you are ten times sexier than her."

Jennifer was feeling aroused as she removed her shorts and top.  She wore a pink bra and matching panties and her friend noticed.  "That's sexy.  I don't believe I've seen you in those before."

She blushed.  "I borrowed them from my sister."

"Does she know?"

She grinned.  "What do you think?"

Jennifer slipped into the outfit.  "Well?  How do I look?"

He gave her a deep kiss as his arousal pushed against his shorts and brushed against her body.  He had grown almost an inch down there since the day they first began having fun together.  "Does that answer your question?"

They walked together, holding hands and kissing as they made their way to the corner of the field and a secluded bench.  "Jenn, I have something I need to tell you."

She looked at him nervously.  "That doesn't sound good."

"Well..."

They sat down on the bench.  "Tell me, Billy."

He sighed.  "My dad got a job out of state, and we're moving in two weeks."

The color went out of her face.  Billy was the only one who knew her as the woman she really was.  "Billy, no, you can't go."

He kissed her.  "I don't want you to cry.  We'll stay in touch, and I'll get back to you somehow.  I promise."

She was crying,  "It's not fair."

He hugged her tightly.  "I know.  I know, Jenn.  I'm gonna miss you so much.  You know I love you, right?"

This was the first time he said those words to her.  She knew how he felt, but to hear the words meant more to her.  She kissed him.  "I love you too."

He stumbled for the words he wanted to say.  "Jenn, I was wondering if maybe you...  If you wanted to try what we've been talking about?"

He wanted to make love to her, and they had talked about it for a while.  She was afraid it would hurt but had started using a vibrator to get used to having something inside of her.  She wanted this as much as Billy did.

Jennifer smiled and gave him a look that said yes, but she confirmed it with her words  "Billy, yes, I do.  I want you to be my first.  You've been so sweet to me and..."

Billy kissed his younger friend passionately and the two kissed for several minutes as he removed his his shorts and underwear.  Jennifer got on her knees and sucked her friend for a few minutes before stopping and removing her panties.  "I want you inside me."

Billy grinned.  "Aren't you gonna remove the skirt?"

She giggled.  "Why should Lisa be the only one who gets laid in this outfit?"

Billy laughed.  "Oh, you are a naughty little slut, aren't you?"

She kissed him.  "No, I'm your naughty little slut."

Jennifer bent over the table as Billy lifted up his skirt and lubed up his sissy girlfriend's ass.  He stuck a finger in and then two.  "I'll try to be gentle."

She looked back at him.  "As long as you fuck me."

"Here goes nothing, " he said as he poked her sphincter.

"Sweetie, you forget I've been sucking your cock for how long now?  That is far from nothing."

He shoved it in and Jennifer  moaned.  He stopped to check on her. "Keep pushing in.  I'm okay."

Billy managed to get most of his cock inside and gently began thrusting in and out.  "Oh, fuck, you are so tight, baby.  This feels so good."

"Tell me about it, " she said as she looked back.  "You have no idea how long I have wanted this."

He increased his pace.  "Yes I do. I wanted you to be my first too, Jenn.  You've always been a woman to me."

The pleasure they felt in that moment allowed them to erase the whole world from their thoughts.  All that mattered now was pleasing each other.  Jennifer rolled over and lay on her back and Billy reentered her.  "Fuck, Jenn, I don't know how long I can last."

She smiled at him as she felt him stroke her cock. Words gave way to sounds and passionate grunts.  Anybody could have been watching them on that bench, and they wouldn't have cared a bit.  The only thing that mattered was the impending orgasm they both wanted.

Jennifer came first as Billy stroked her cock.  A few moments later, he shot his seed into his sissy girlfriend's ass.  It seemed like it was a big load, and She felt the warmth within her   He stood there looking down at Jennifer for a moment with his cock still inside her.

The two held hands and lay down on the grass together, kissing and making idle chit chat before they drifted off to a short nap together.  It was a moment they never wanted to end.  Unfortunately, it did end, and Billy moved away two weeks later.


Bill took a bite of the chocolate cake he ordered for dessert.  "So, what ever happened to that cheerleader outfit I gave you?"

Jennifer grinned.  "I kept it, of course.  I wanted to remember that special time in my life.  Lisa's daddy had money.  He could afford to buy her a new one."

Bill laughed.  "I love it.  You go girl."

They enjoyed their dessert and one more drink for the road before Bill got up to catch his cab back to the motel.  He hugged her and gave her a kiss on the cheek.  "You know, Linda knows all about you and I, and she's quite open to you joining us if..."

Jennifer gasped and her face turned red.  "Billy!"

He broke the hug and turned to leave.  "Just putting it out there."

Jennifer watched him take a few steps towards the door.  "Bill!"

He turned around.  "Yes."

She smiled.  "Tell her, I said maybe."