Jennifer's Big Night Out Ch. 02

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Jennifer's night out with the girls continues.
3.5k words
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Part 2 of the 4 part series

Updated 06/09/2023
Created 02/17/2020
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"Are you ready sexy?" asked Beth, offering the dress to Jennifer. Immediately her cock started to grow at the idea.

"Now do you see why we couldn't go with the red dress" said Tanya. "That thing would be poking out the whole time and spoil the illusion."

"Should we let her...you know..." said Beth shyly.

Tanya went very red in the face. "I'm not sure that would help, to be honest Beth. That's why I picked the dress that flares out a little bit...to avoid... em...tenting."

Jennifer stood silently, head down, as the girls discussed her erection which was simply getting harder.

"Let's get it on and see where we are. We still have to get ready and maybe it'll go down."

"Oh yes" said Beth "cross dressers often lose their hard-ons when pretty girls pop them into wedding dresses. It's a well-known fact." There was silence for a second. Then all three burst out laughing.

"C'mon" said Beth "let's get you into this then we can sort the petticoats and hide it. It would really help Jennifer if you were like most sissies and had just a little dicklet."

"Oooooo there would be so many more options for us then" suggested Tanya, who was silenced by a look from Beth. Jennifer caught it and wasn't sure if that meant they had planned something else, or Beth was just aware that talk of dresses and outfit and being dressed wasn't making the problem go away.

"Step into the dress Jen. Point your toes so the heels don't catch."

Jennifer stepped into the dress, then Beth eased it up over her ass and around her boobs. She could feel Beth's own breasts pushing into her back. Tanya moved to the front and slowly pulled the dress up over the breast plate and took the collar and fastened it, covering where it the join could be seen on the neck. She straightened out the V lace insert which dropped as low as Jennifer's navel. The sleeves were short and puffy. Beth appeared with a big petticoat and had Jennifer step in again before pulling it up under her dress. She then fluffed it out, making the skirts stick out.

"What do you think?" asked Beth.

Jennifer looked in the mirror. She looked amazing. Her make-up was wonderful and the dress hit around mid-thigh. With the petticoats, it was impossible to tell she had a raging erection which she wanted to deal with, but was much too embarrassed to touch herself. Her boobs looked incredible. They looked so real, locked behind a little film of lace. She looked like a bride. A very slutty bride, but a bride nonetheless.

"Christ, I don't think any of us has looked as good in this, not even Rina." It was not a name recognized but Beth nodded at Tanya's reference, so could only assume this was a friend he hadn't met. "My god, that guy followed her around all night. She couldn't get rid of him."

The girls kept walking around Jennifer like she was some work of art. And in Tanya's mind she was. "The petticoats solve the problem. Look...if you don't mind Jen" said Beth. Jennifer shook her head as Beth pulled up Jennifer's skirts to show her erection pushing hard against the French knickers. "That was such a great idea Tans."

'Ok, we need to get ready. Do we trust you not to play with your cock?"

"I don't know if we do Beth. She could stay in here and I could keep an eye on her."

"I don't think so."

Jennifer suddenly felt very excited the girls were squabbling over her.

"She can sit in the lounge. Not even this over-excited tart is going to risk bashing one out with the floor to ceiling windows. And no closing the blinds you sexy girl. Come. And I don't mean that literally. Or metaphorically. Or whatever the hell it is. Just don't touch your cock." Beth took Jennifer's hand, lifted her wine glass and led her into the huge living room. "Watch whatever you want on TV. There's no porn, so don't go there. We won't be long and I need to get you some jewellry and listen for the buzzer for Jayne."

She gave Jennifer a long hug "Oh you are such a sexy girl. I wished we'd gotten your belly button pierced. It would have been so horny in that dress. Still," she said flashing a smile "the night is still young and who knows what'll happen." She kissed Jennifer on the cheek and skipped into her room. Jennifer watched her gorgeous ass disappear and moved towards the mirror on the hall closet.

"Fuck, I know I've put myself in some situations recently, but I do look amazing. And I am going on a girl's night out. With three very sexy girls." Jennifer didn't finish the thought. Instead she drained her wine and went to sit down.

After 20 minutes, there was a call from Beth's room "Jen, can you help me out?" Again, she liked when Beth called her that. It felt familiar and warm. Jennifer walked over to Beth's room and gently rapped on the door. "You decent?"

"No, that's the problem, come in quick." Jennifer walked in and Beth was struggling to zip up a very tight pvc dress. "Can you help me?"

Jennifer stood behind the gorgeous young girl and eased the zipper up slowly, past Beth's bra and slowly into place.

Beth turned around. "My god that's snug" said Jennifer.

"I need something to take some of the eyes off you. You like?" said Beth as she threw her hands out to the side and cocked her hips. Her breasts were full and round and the black pvc clung to every wonderous curve. Jennifer was grateful for the petticoats because she felt herself stiffen again. She swallowed hard.

"Well?"

Jennifer realised she hadn't said a word. She managed to croak a quick "Yes" and then tried to look somewhere that didn't put Beth's boobs in her eyeline.

"Good! That was the sort of impact I was hoping for, although I'm hoping some guys will react like that too." Beth sensed Jennifer's face falling slightly. "Oh Jennifer, I just mean when I see you all dressed up like this, I don't see you as a guy. I see you as one of us. Although I hope..." Her hand snaked towards the bottom of Jennifer's dress. Jennifer instinctively pulled back.

"Oh my god, I'm so sorry. You're right. I have no right to do that to you. Please forgive me."

"Beth - it was an instinctive reaction on my part, but I appreciate the apology. And I know what you were trying to do. I think we're kinda past that point in our friendship. You can do that sort of thing" Jennifer smiled. "If it's any consolation, to use a phrase from your mother, looking at you - it was as hard as a baseball bat."

Beth laughed. "I am sorry. I promised to protect you and here I am trying to feel you up before we are even out the door. I've got your back girl, I promise."

No sooner were the words out of her mouth than the buzzer went. 'That'll be Jayne, let's go let her in."

Beth buzzed Jayne up and opened the door to the apartment. Jennifer didn't quite know where to stand or how to feel. She knew she looked amazing. She knew she found Jayne incredibly sexy and pretty. And she knew she had been really mean to her when she served as a bunny server, making her lick her out then later grinding herself to an orgasm when Jennifer was tied and helpless on the bed. She was worried that if there were any problems tonight, Jayne would be the source.

"Relax, it's fine. She'll be on her best behavior." Beth grabbed Jennifer's hand and squeezed. It was a reassuring gesture which helped calm her ever so slightly.

Jayne walked in and looked amazing. She wore a high neck red dress which clung to her glorious curves. Jennifer had never noticed before how large and wonderful her boobs were before. Her tiny waist was cinched with a broad black belt, and she was bare legged but wore black four-inch stilettos. She was gorgeous.

She walked straight over to Jennifer. "Oh my god. I thought Tanya was going to be our bride tonight. Jennifer, you look amazing. What's with the boobs? They are magnificent."

"Breastplate" added Tanya who had joined the group. She looked stunning. Her red hair hung loosely over her shoulders. She wore a silver top with a cowl neck which gave a hint of her wonderous cleavage. She wore the tightest leather leggings Jennifer had ever seen and was perched upon four inch patent leather heels.

"From downstairs" added Beth.

Jennifer felt relaxed enough to give a small twirl and the three girls clapped excitedly. "Oh man, we are going to have so much fun" said Tanya grabbing Jennifer tightly. Then the other two jumped in for a group hug and Jennifer was again grateful for the petticoats as she felt her cock rising in her silky panties.

"Nails and a ring" said Beth. "We need to finish the look" as she headed off to her room.

"Can't have a bride to be without a ring" added Tanya walking off too.

Suddenly Jennifer and Jayne were alone together for the first time since after the party. "Don't look so scared bunny bitch" said Jayne. Jennifer's heart sank. "I promised Beth I'd be on my best behavior and I will but that doesn't mean I can't have some fun." Her niceness had been a front. And now Jennifer would have to be on her guard the whole time. And she wasn't sure Beth would be able to help.

"I remember you telling me you wanted to have a guy fuck you." Jennifer hadn't really meant it. She just said it in the hope Jayne would stop tormenting her when she bombarded her with questions at the bunny party. "Well on your last night of freedom before the big wedding, maybe we can make that happen."

Jennifer swallowed hard and suddenly finding some courage looked Jayne right in the eye "I don't want that. I want to have a fun night and if you are going to be a bitch, I can go and change right now. Or would you like me to tell your friends about that things you told me when you dry humped me the night of the party?"

Jayne's face fell. She looked genuinely shocked. And in that moment, Jennifer realised she was so drunk she couldn't remember exactly what she said. It hadn't been too awful or revealing, but Jayne didn't know that. For a second she almost felt sorry for her. But the feeling quickly passed. She needed to press home her advantage.

"So we understand each other?" Jayne mumbled something.

"Sorry. I couldn't quite hear."

'Yes we do."

"We do what?" asked Beth suddenly reappearing.

"We agree to look out for one another tonight - don't we Jayne?"

"Yes".

The girls produced some fake French manicure nails which they glued on to Jennifer's hand, then placed a large fake engagement ring on her ring finger on her left hand.

"What's the story?' asked Tanya

"Marrying a boy called Daniel in two weeks at the family pile in Hampshire. This is the pre-Hen before the big outing next weekend in Dublin before Jennifer here signs up to a life of golf club dinners and crushing society balls with her multi millionaire older husband."

"Beth, where did you come up with such a back story?" asked Jennifer.

"My mum isn't the only one in the family with a creative bent" she replied beaming slightly.

"Right girls. Pub on the corner then into town" said Tanya leading the way out the front door. They certainly made a glamorous and incredibly sexy group as they made their way down the stairs giggling and chatting excitedly. Just as they passed Apartment 4 a quite sleazylooking guy opened the door.

"Hi girls. Need some company?"

"Were you looking through the peephole again Derek. Playing with your little willy waiting for us to pass by? You are such a douchebag."

"Jayne. Sweetie. You really need to get better at your flirting. That's not going to convince me to jump in the sack with you. I hope your pillowtalk is better. I do love it when girl's talk dirty."

"Ewww..." Said the girls in unison.

Jennifer thought Derek was probably in his late twenties but dressed like a guy in his forties, He had dark hair and was obviously fit and well off. But Jayne was right. He was sleazy. Especially as he was staring right at Jennifer's boobs.

"And who is the gorgeous addition to your group? We haven't been introduced. I'm Derek. I work at Goldman Sachs and the Porsche you see outside is mine. You should ditch this lot. We could have a great time." He put out his hand to take Jennifer's but accidentally on-purpose brushed it against Jennifer's boob.

"You know, acting like a dick won't actually make yours any bigger" replied Jennifer, turning and sashaying past. The other girls hooted with laughter. Derek could only stand with a dumb look on his face, crushed.

"Bye Derek. Better get that burn seen to" shouted Beth.

As they hit the street, Tanya grabbed Jennifer by the arm. "That was fucking brilliant. What a line. Oh, I am so stealing that. You are a sassy little minx aren't you? I think you are definitely going to fit right in." The girls linked arms and giggled all the way to the pub. Jennifer felt part of the gang.

As they stood in the pub drinking, Jennifer quietly looked around. This was the first time she had been out in public as a girl. It was easy to forget that when she was caught up in the fun being transformed. It made her nervous and excited. Essentially, she was a very well made up boy, standing in the middle of a bar with a very short dress, lacy stockings, gorgeous fake boobs and high heels. A few people were looking right at her and it made her uncomfortable. Had she been read? Did they know she was not really a girl?

"What's up sexy?" asked Beth sensing something wrong.

"People are looking. Do you think they know?"

"You are dressed in a tarty bride's dress with an L plate on the back." Jennifer hadn't noticed that addition and tried to turn to see it. "Thank Jayne for that, but if they are looking it's because there are four hot girls standing at the bar and you're one of them. Get used to it sexy - this is what happens to the hot girls Guys stare all the time. Girls get jealous."

Tanya overheard the conversation. "Let's give them something else to look at" and she suddenly took Jennifer's face in her hands and planted a long kiss on her lips. Jennifer was quite taken aback but loved it. She felt herself stirring down below and when Tanya pulled herself off, Jennifer checked there was no give away down below.

"You're kidding right?" asked Tanya. "That would be enough?"

"Tans, she's horny all the time" laughed Beth.

"Look" said Jayne. "All those boys are staring. Those are the hard dicks you need to worry about", which made the girls laugh again.

There was a group of boys standing to the side. It was clear they were interested but struggling to muster the courage to approach the four. Jennifer recognized the types from her own friends. There was the tall, good looking one who didn't say much. The plain, average guy who seemed to be the joker in the bunch, the better than average confident loud mouth and the smaller, quieter reserved boy whose insecurities had him clinging to the edge of the group. Jennifer felt an empathy for him. That was Dan. Or her. Or her when she was Dan. She was no longer sure.

Confident loud mouth strolled over. "Can I buy you girls a drink?"

Jennifer wanted to say no but Jayne quickly answered "Great, Four gin and tonics."

Jennifer looked at Beth, who whispered in her ear "Don't worry, a drink doesn't commit us to anything." Confident signaled back to his mates who then wandered over, not quite believing their luck.

Introductions were made. Jennifer only said her name once, worried saying anything more would give the game away even though she could affect a pretty feminine tone. She discovered the boys were Mike, Pete, Ren and Ashley. Ashley was the quiet one.

The boys asked Jennifer about her Hen night and upcoming marriage but Tanya and Beth ran interference answering most of the questions. Jennifer was smart enough to sip from her drink just before they asked something. It avoided conversation but meant she was getting a little bit tipsy. They asked where the girls were going. They just looked nervously at each other. Clearly something was planned they didn't want to share with Jennifer at this point. "Just a club" said Jayne.

"Maybe we'll join you there?" said Ren hopefully. Jayne laughed but didn't give an answer.

Ashley turned to Jennifer and said "I like your dress. And your shoes." It was an odd thing for a guy to say and suddenly she found herself wondering if he was quiet and reserved like Jennifer because he was just like Jennifer.

"Thanks. When you say my dress, it normally means my boobs."

"No. I did mean your dress" said Ashley clearly flustered by the whole exchange.

"Thanks. You don't speak to many girls do you?"

"No" he said stammering "But you are so pretty I had to say something."

It was Jennifer's turn to feel flustered. "Thanks."

The girls were finished with their drinks and decided it was time to move on. Jennifer drained her glass and as she turned Ashley leant in "I think you are gorgeous and something tells me you are kind of special. I know you're getting married but I hope we can meet up later. Here's my number. Text me. Please."

Not knowing how to react, Jennifer took the card and walked out. The girls were waiting. "Fuck me, four of us there and the tranny is the only one that gets hit on."

"JAYNE. You're out of order. Jennifer is one of us this evening and you need to respect that." Beth was keeping her friend in line.

"I'm sorry, but Ren was really fit, and even when I rubbed my tits against his arm I got nothing back. Meanwhile the wimpiest one there hits on the bride to be? I mean, what the actual fuck."

Tanya laughed. "Actually, when you put it like that, it is pretty funny." The girls laughed. Even Jennifer saw the funny side.

The evening took them through a few more bars. The girls hardly bought a drink. There were plenty of guys around who wanted to impress them. And Jayne eventually got her phone number, although she crumpled it it and threw it away as soon as she left the bar. "Loser and I bet he's got a needle dick."

Jennifer almost forgot she was a boy. Some girls complemented her on how pretty she looked, how sexy she was and how whoever she was marrying was a lucky guy. She loved the adoration and found her hidden cock bouncing up and down on a regular basis with excitement, giving her an extra thrill. She had no idea what the red dress looked like, but she was glad she wasn't wearing it. One girl approached her, very drunk, and told her she should be ashamed of herself, flaunting her boobs, dressing like a tart with her wedding just a few weeks away. She should act with more modestly. "Like a real lady" she was told. That made Jennifer giggle. Which just infuriated the drunk girl even more. It looked as if she might hit Jennifer when surprisingly Jayne stepped between them.

"You, fuck off. And when you get there, fuck off some more."

Jennifer felt relief washing through her. And she also felt a real bond with these girls. Was she friends? She wasn't sure. But she had been accepted as one of them. This was a real insight into a life she never thought she could experience or enjoy. And now here she was living it. "Are your nights always like this?" she asked no-one in particular.

"Believe it not this is quite quiet" replied Beth with Janye and Tanya nodding in agreement.

As they left another bar, Jennifer felt quite tipsy. They were close to a number of nightclubs. It was getting late and even though she was feeling a bit tired, she wasn't ready to go home yet. She saw Tanya and Jayne talking and inserted herself into the middle of the conversation.

"So where are we going for the big finale? I want to dance."

"Well, we have something special planned. And you'll definitely get the chance to dance" said Jayne.

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3 Comments
AnonymousAnonymousover 3 years ago
so hot

dam I want to be jenifer so bad

darthnader19darthnader19about 4 years ago
5 stars

Amazing as always cant wait to see how the night continues

AnonymousAnonymousabout 4 years ago

why couldn't they tell people she was marring a woman????

after all he has been forced blackmail into gay sex and got raped by it at the hands of beths mother

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