Pretty in Pink Ch. 04

Nis 15, 2024 // By:analsex // No Comment

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Ass

Having a lifelong fetish for sexy lingerie was exciting, but my concern was having someone catch me wearing. After my wife, Jessica found out about my stash of women’s clothing, I thought my marriage might be over. Her eventual understanding, learning and acceptance of my little kink was a life changer for our marriage and my peace of mind. When in fact she began participating in my fetish, I was overwhelmed. She began taking the lead in our role playing games. This worked wonderfully well for my wearing women’s clothing signified a streak of submissiveness in sex. This was linked back to my inferiority complex because I had a small cock.

In the last chapter, I related how she acted out a scenario of being the teenage virgin. Then she reversed the role and clothing, eventually taking my anal cherry. I was blown away with that event, but fell right in line as soon as she began fucking me with her new cock. If there was ever any question about who was in charge, my getting fucked in the ass by my beautiful wife cleared it up. When it came to sex, she became the controller of the level.

Jessica loved being the demure wife in public. I loved the respect she gave me as a man. I also loved her taking the lead in our “Dress Up Games”, as she began referring to my crossdressing. I no longer had to go through the façade of wearing manly underwear. This was very private between the two of us.

I had already debuted as her “girlfriend”. I was astounded that I was not seen as a freak drag queen initially. In order to feel my most sexy, we dressed up on our “Dress Up Dates”. We sometimes felt out of place because we were overdressed compared to the women around us. That seemed to be the focal point of some second looks we got from women. From the men, we got plenty of second looks for our appearance in general. I am sure most of it was according to Jessica’s extreme beauty. Men were so drawn to her, that I think I got passed over as the “second best” woman in the picture. This opened up completely the range of events and places we could go. My confidence grew with each positive experience.

That would have been good enough, but Jessica upped the ante when she started buying more risqué clothing for both of us. The first time she did this, we dressed in short shorts, chorus line sheer to the waist panty hose and stilettos. She picked out a form fitting crop top for herself and a more conservative collared top for me. My bra and breast forms were not showing, but she had pushed up my own man boobs and applied the subtle makeup that gave me some really nice cleavage. She had already insisted and I had my belly button pierced. Now I added a dangling ring there to match hers.

We drove down to the beach one Friday evening, arriving around ten o’clock at the club we found. We were dressed to kill and my makeup was perfect. I had on a dark brunette wig just below my shoulders. I wore long dangling earrings. We quite noticeably strutted into this place like we owned the night.

Inevitably, guys began flocking to us and asking to dance. This was the ultimate test and Jessica had instructed me how to cope with this. I was to be in character, but not too obvious. She explained that we were two single girls out for a good time. We were not looking to get picked up. I was of course nervous as hell. Going out with Jess as her “girlfriend” had gone very well, but dancing with a guy would be the ultimate test. I did not think I could pull it off.

Jessica had worked with me on our eating and shopping trips to help me develop a female voice without being too high pitched and obvious. For some reason, I had blended well. My masculine voice was not bass in tone, more neutral and relaxed. I just added some casual pitch and Jessica was amazed at how easily I had transposed to the voice. We even sang songs together when we were driving.

Two guys approached together. (Thankfully) They each chimed in together, “Wanna dance?” Jessica had demonstrated how you extend your hand to accept. I did not have to speak. We made it to the crowed dance floor where couples of every color and style were flowing to the snappy music. My guy shouted and extended his hand, “I’M DANNY.”

I shook his hand and shouted, “BRIANNA”.

I danced as rhythmically as I could and still be feminine. As I watched other girls dancing I got a good idea of what was normal. I saw Jess out of the corned or my eye. She was watching me carefully. It was comforting to know that she had my back. The music was so loud, that any attempt and real conversation was futile. So we shouted and smiled some. It was just the right contact for my first time out.

My heart was pounding and I was trying not to sweat. I was afraid my makeup would start running. Just for safety sake, Jessica and I had worn necklaces with lots of beads that dipped down toward our cleavage. Danny and I danced two fast numbers and I smiled and breathed heavily signifying that I had had enough. Danny escorted me back to niğde escort the bar where he bought us a drink. This worried me because I did not want to go one on one with conversation just yet. Luckily Jessica and her dance partner showed up just then and joined us for a drink. Jess took the lead in the conversation about who we were and where we lived. She was great and I don’t remember much of the content except that she kept passing easy questions to me. I was able to get by with minimal words. I just answered in short gasps as I placed my hand to my ears to show that much conversation was not possible.

I am sure the guys had every intention to hit on us, but we settled for more dancing with them. Again the floor was crowded and the music was booming. Danny and I smiled, touched each other casually and continued dancing. I signaled that I was done after the music paused and we went back to the bar. I hugged him casually and kissed his cheek. I thought that was a nice touch. Jessica and her partner returned and we began talking again. Just as the guys started their lines, Jess cut them both off, “Great meeting you guys. Brianna, have you seen Cal and Lisa, yet?”

To the guys, she explained, “We are meeting some friends here. How about we dance some more later?”

We gave each guy a quick cheek kiss and wandered off appearing to look for our imaginary friends. I casually touched Jessica’s hand and whispered, “Thanks.”

“Oh, my god, Brianna, you were great. I watched you dancing and you looked so relaxed.”

I replied, “Yeah, looks are deceiving. I was scared to death.”

Thank goodness the crowd was so large, for we blended into the writhing mass on the dance floor. As we worked our way through toward the opposite side, Jessica touched me and started dancing solo. I followed and we looked like two hot girls on the dance floor. We laughed and moved along, not wanting to give the impression that we were together in “that” way. It was so much fun not wanting to appear as two lesbians while we were dressed so hot. The irony was wonderful.

We decided not to push our luck. The goal was for me to get closer to people and work on my feminine skills. Jess and I both felt that the evening was an unqualified success. When we made it back to the parking lot we did kiss and feel each other up. Now we knew that anyone looking into our car would indeed mistake us for two hot lesbians.

My cock was bulging a little under my gaff, but it just felt a little tighter. We wished we had worn skirts because the short shorts made it harder to feel each other. She unbuttoned my shorts and pulled them down exposing my satin thong. The chorus line pantyhose were so sheer and they looked great on our smooth legs. In return, I unbuttoned Jessica’s shorts and helped her slither out of them. She cranked up the car and we headed back home. We felt each other all the way back home and had great sex once we arrived.

The following week, Jessica texted me on Friday morning. She asked,

ARE YOU UP FOR DRESSUP TONITE??

I texted back,

YES.

That evening, she showed me what she had bought for my second night out. It was a short black leather skirt, black sheer pantyhose, red bikini panties and a sheer red top. The top buttoned all the way down. It was unbelievably soft. I wore a matching red demi bra. Jess used some cleavage tape on my boobs and stuffed the bra with two cleavage enhancers on each side. I was trussed up tight. She again applied the subtle makeup to make my cleavage look even bigger. When I buttoned it up, she stopped me right at the line of my bra. You could see plenty of cleavage.

She did my makeup in dark colors and added some red tint to the eye shadow. The fake lashes were exceptionally long. She added a red highlight where the lashed attached to my own. This was by far the most eye makeup that Jessica had done for me. The rest of the makeup was masterful as always when she made me up.

She pulled out a dark brunette wig that touched my shoulders. When she adjusted it and perked it up, I looked back into the mirror. I looked like an exotic beauty. She painted my lips with a dark red color. When I put on the sexy six inch red pumps, I was ready to go.

Jess wore a short navy mini skirt with a red scooped neck. She wore a bra just like mine, but the swell of her breasts was simply amazing above the neckline. Her makeup and hair were gorgeous, just like mine. With her deep tan, she went without pantyhose or stockings. She slipped into a pair of navy heels and we were off.

I asked where we were going. She told me downtown to one of the chic nightclubs. She drove again. That was always a good idea since we did not trust my nerves. We pulled up and stopped, gave the keys to the valet and went inside. We had no trouble getting in with the way we looked. By now, I would have been stunned if anyone had made a comment. I was fully “Brianna”.

Once inside, I asked Jessica where ordu escort we were going to sit. She laughed and said, “Well, Brianna, we are going to split up tonight. You have done so well that it is time for you to solo.”

I was shocked. I had always had her nearby so my confidence was always there. I asked what that meant.

“Well, Honey, it depends on what you can attract as a dancing partner. I am just concerned that you may attract a better looking guy than me.”

“What if the guy gets a little handsy?”

“I hope they do. Just react like any gorgeous horny girl would. If one wants to feel your ass while dancing, go ahead. If one tries to kiss you, just stay in character. You don’t have to swap spit or anything, but you can kiss him back. You know how. If he wants to feel your breasts, allow a light touch.”

“As far as feeling him up, just be careful. You don’t want to get too far or you might be thought of as a prick tease. However, if you are feeling frisky, why not grab some cock while we are having a good time?”

I was already shaking. I did not think I could pull it off. Jess told me that we should meet up at the entrance around eleven o’clock. That would give us a couple of hours to circulate, dance and whatever. She told me to slowly walk up to one of the standup bars and order a drink. Then I was to stand there or move around a little until someone asked me to dance. With that she was off on her own.

I walked over and ordered a strawberry daiquiri. When it came, I paid with a bill out of my pocket. Luckily it was not long before a man of about thirty walked over and started chatting me up. His name was Barry and he asked mine. I had no trouble getting out, “Brianna”. I was feeling the daiquiri and beginning to find my tone as I answered his questions. I just had to be careful to get the pitch just right and try not to exaggerate a shrill tone. He was just under six feet tall and I was just a little taller than he was in my heels. It was no big deal, because the heels made up the height. He did not seem intimidated in the slightest.

Finally, he asked me to dance. The music was in between tempo and hard to dance to. He laughed and said he was a terrible dancer. I told him that no one could dance to that. We got close and tried it at slower pace. This way he could talk to me. I answered each question as shortly as possible without being rude. Jessica and I had worked very hard on my smile and laugh. I felt comfortable laughing at his comments. The music got faster and he invited me to dance to it. We did better on the second number.

After the dance, I told him I had to go to the ladies room. This was a ploy to keep guys from getting too close too early. I told him we should catch up a little later and dance again. I strutted out to the foyer and entered the ladies room. I checked my makeup in the mirror. So far it looked great. I entered the stall and did a little pee. I wiped the end of my cock and made sure in was drained before I put it back into my panties.

When I got back to the bar, I was ready to order another drink. While waiting, a tall young guy asked if I would dance with him. He introduced himself as Lee. He was late twenties was just over six feet tall. I was almost level with him in my high heels. When we danced, he held me close and moved very rhythmically. I was doing very well at this pace. Lee whispered in my ear,

“Thank you for dancing with me, Brianna, you are just beautiful and tall in your pretty red heels.”

“Oh, my, thank you so much, Lee. You are a real cutie yourself.”

We danced a few numbers and he got a little closer each time. He kept complimenting me and said, “Damn, you are hot and your perfume is intoxicating.” That was a detail that would have escaped me if Jessica hadn’t insisted on me wearing just a little too much perfume. I thanked him and he pulled me closer. This time he moved his hand a little further down my ass. He was moving it slowly but deliberately. My leather skirt was on fire now. I did not know how to react. I was trying my best to remember and feel like Brianna would react. I moved under his hand and he felt emboldened. He moved it up to the small of my back and caressed the soft material of my sexy top. I patted the back of his head with my hand. I wore several rings. Jessica said it would make my hands look more feminine. My nails were long and red already, but the rings added another dimension.

Just after I patted his neck, he pulled my head closer and we danced cheek to cheek. The song ended and he kissed me on the cheek. I was shaking. I knew I was not gay, but the feeling was electric. I could not explain to myself why either. The music changed again and he held me closer. As the tempo increased, we separated slightly and I turned my back in rhythm. He pulled me back to him and pressed his cock firmly into my backside. Even through my skirt, I could feel his firmness. He then reached around me and pulled my stomach back rize escort to him. We dance this way for a while as he ground his cock into me. Then ever so carefully, he moved his hand up to my breast and closed it around me.

I spun back around and gave him my sexiest smile while I placed both hands on his shoulders. He put both hands around my waist and pulled me closer, then kissed me on the lips. I kissed back just as Jessica had instructed.

The music ended and we got a table. We were sitting at each corner of the table so we could look out over the dance floor. I crossed my legs and my skirt rode up showing almost all my pretty legs. Lee placed his hand on my knee to test me out. I did not react. He continued to move up my leg and we talked and laughed. He leaned forward and kissed me again. I took his head in my hand and pulled him closer and gave him a slow kiss.

I was totally in character now and Brianna was acting very compatible with him. He ran his hand further up my legs. My cock was so tight under my small panties that I knew it had no chance of escaping. If he made it any higher, he might feel the V in my panties. I could see his cock bulging and it looked big compared to my own. I could not tell exactly how long he might have been, but it was making a pretty good tent in his slacks.

Luckily, Jessica had her eye on me now. She waited as long as she could to give us a chance to go further, but not too far. Just at the right time she appeared and said, “Brianna, hey girl, thought that was you. How are you?”

This broke up the groping and I introduced her to Lee. She shook his hand and gave him a quick peck on the cheek. I invited her to sit down and have a drink with us. I could see that Lee was disappointed although he tried to hide it. Jessica talked like we were close friends. She talked about some of her girlfriends and made it seem like they were “our” girlfriends. She shared some harmless gossip. Finally the drinks arrived and Lee offered to get them. Jessica said, “No way, I intruded, it is my treat.” She pulled some bills out and placed in on the waitress’ tray waving her away as saying “Keep the change.”

As the music changed again, I said, “Jess, Lee is a great dancer. Lee show Jessica some moves. I will sit out this one.”

Jessica picked up where I left off and when the number ended, she kept Lee on for the next number. She was flirting her ass off. She touched him and held his neck. They danced closer. I swear by the time they had danced a few numbers, he had felt her soft breasts and great ass. I slipped out to the car and ten minutes later, Jessica came out. We laughed and giggled all the way home.

Back in our bedroom, we were kissing and touching. We were so excited. Jessica wanted to tell me about her evening and how she was able to spot me getting felt up. She had seen most of my intimate moments and I wanted to hear what she had done first.

Jessica told me that she had watched me a little at first, and then a tall black guy had asked her to dance. She readily accepted. I was surprised that I had not seen her. She said that I was probably too nervous. She danced three or four dances with the black guy and he was coming on pretty strong. When she did not block his advances, he began holding her tighter. He felt up her ass pretty good and told her how hot and sexy she was. She said that having a big man hold her this way was very different from being with me. She said that it must have clicked in her brain and she felt small and fragile with him. However, she said, that she soon remembered that the woman has control.

With that in mind, she let him progress until he leaned down and kissed her on the lips. She said, “What the heck, we are trying new things tonight.” She returned his kisses. As things moved along, he suggested that they get a table and have some drinks. She went along with this. The guy, Alonzo, was moving a little fast so she had to pace herself. She did not want to get compromised. She had to remember herself what she had told me about not becoming a prick tease. Something bad could come from that.

She told him that her girlfriend was there also and she had to cool it a little. He moved over next to her and started rubbing her leg. It sounded familiar to me and I excitedly told her about Lee moving his hand up my legs. So, Alonzo was hot to trot and was trying his pickup move too early. He kissed her with passion and even searched her mouth with his tongue. She sucked his tongue deeper and he moved his hand up to her panties.

Jess then told me that she spread her legs to allow him access and he began rubbing his hand outside her panties. He was feeling her shaved pussy and making her wet. She moaned a little as he pushed a finger under her panties and sunk it into her tight pussy.

She said, “Honey, I am sorry, I let him go too far, but it felt so good. I really wanted him to fuck me then and there.”

“I knew I had to stop. So I told him I had to pee and he was about to make me cum.”

“He was hard as a rock and his cock was way out of his boxers and down his leg. It was huge, Baby. It must have been this long.”

She put her hand on her other forearm not quite to her elbow.

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