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."