• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Terri Goes on a Date

Terri Goes on a Date

It was early August during the late 80's in San Diego I was still wondering who it was that that had come into my booth at the bookstore the week or so before and came all over my face, but was no closer to knowing.

We had a few reservists serving on the ship for their annual two week training and there time was about up. One guy Chris was assigned to my division for the second week of his AT. He was from Vegas and seemed like a good guy. On Friday afternoon he came over to me and asked if I wanted hit the bar with some of the other guys that night. It was his last weekend before going home so I said sure.

Five o'clock came and we got ready to leave for the day. Chris came with me and we put his sea bag in my car then headed out to get some pizza for dinner. We were supposed to meet the guys at the club later around nine. After we ate we went back to my apartment so I could take a shower. Chris got a beer and turned on the TV while I went in to take a shower. I stripped down to my lace panties and started running the water. While I was waiting for it to warm up I realized I had left my nightie and panties from the night before on my bed. I figured he wouldn't come around behind the wall separating the rest of the apartment from my bedroom and find them so I climbed in the shower and closed the door. Little did I know that while I was in the shower Chris was snooping around my apartment and found those items and much more.

I got out of the shower dried off and walked out to get some clothes out to wear. Chris was standing there holding the nightie and panties. I was for a second time in a week found out. He asked if the panties he was holding were the ones I was wearing at the bookstore the other day and grinned. I replied no actually, I just took those ones off.

He started asking questions about my crossdressing, like do I wear makeup and wig, do I ever go out in public fully dressed as a women and so on. I told him that yes I do wear make up and actually had a girlfriend I met at a boutique by Hotel circle that had taught me to do makeup, walk more like a girl and is working with me on my voice as well. I explained to Chris that she liked to have sex with me dressed as a women, which makes it fun for both of us.

Liz was the one that got me to go out public dressed because she convinced my I was every bit as feminine as a women when I was all done up. I was 5' 8" and only 150 pounds and very thin in a feminine way, with a naturally smooth body so she taught me how to be Terri and we went out shopping and to clubs on several occasions.

Chris looked at me smiled and walked over to my closet and started looking through the clothes I had and there was a lot to look at. He pulled out a cute black knee length dress with a flare to the skirt and put it on the bed. I asked what he was doing and replied picking out your clothes for tonight. He then went to my dresser and started looking through it and pulled out a pair of panties, bra, slip, stockings and shoes followed by picking which of my three wigs he wanted me to wear and told me to get dressed for him. It was such a turn on to be ordered around like this.

I slipped into my panties and bra as he watched me. I could see a bulge begin to form in his pants. He walked way and I continued to get ready. I was putting on my makeup when I noticed him standing behind me with a camera. He started taking pictures of me getting ready. I had on my panties, garter, stockings, bra with breast forms in and my half slip. I picked up the dress and smiled at him saying that he needed to wait in the other room so there would be some element of surprise. He snapped a picture and walked away.

I slipped into my dress and heels then put my wig on. I went back to the mirror for final adjustments before walking out to him. His eyes got very big as I walked out and he told me that nobody would ever know that I wasn't a women. I smiled and turned to him so he could zip up my dress. After he did a spun around for him to get a good look as he took more pictures. His cock was pushing through and It needed attention so I got down on my knees and undid his pants. I sucked him off, but he came so fast I was done in no time.

Ok its time to go he said after he zipped up his pants. I asked were and just said you'll see.

We drove around for about 20 minutes or so with his hand on my thigh rubbing and squeezing me. When we reached our destination I thought for sure he was joking. We were at the club that we were supposed to me other guys from ship at. I had been here dressed once before with Liz and even made out with a guy and gave him a hand job, but tonight was different, I worked with these guys every day. I told Chris no way am I going in there with those guys all in there, they would for know it was me. He assured me that nobody would ever know it was me. The lighting was low and they were drinking so I would be fine.

He got out of the car and came around to my side opened the door for me. I just sat there for a minute and the he reached in and helped me out. He gave me a kiss and told me how good I looked before we headed in.

The other guys saw Chris and I walk in and waved us over to them. I thought for sure they knew it was me, but If they did they sure didn't let on that they did.He introduced my as my own cousin Terri visiting from RI saying that I (Scott) would try and get here later. It was working too, and boy were those guys checking me out.

We ordered drinks and sat down while we all talked many of them asking me how long I was in town for and so forth. I felt a hand rub my ass or thigh on several occasions and Chris noticed it too. He leaned over to me and told me they all think you're hot and smiled at me. I kissed him and then we got up to dance.

We did a lot of grinding with my pushing my ass into his crotch. I could feel his cock getting hard as we danced. We went to sit back down and one of the guys asked me to dance so I went out on to the dance floor and helped him get a hard on too. I sat back down on the couch next to Chris and he started to rub my thigh again, as he did he was hiking up my dress more and more. Eventually my stocking tops were fully exposed and the guys made no attempt to not stare.

Chris and I were soon making out as he continued to work his hand under my dress. We were joined on the couch by one of the other guys from the ship. I started talking to him and it wasn't long before he started rubbing my other thigh as he talked to me.

I could see his cock was enormous through his pants. I reached over and rubbed it and he moaned. It was dark in our corner so I asked him to un do his zipper and slid my hand in to find a monster 8" cock just ready to explode. Chris meanwhile started to kiss my neck has I gave Bret a hand job. I told Bret to let me know when he was going to come because I wanted it in my mouth. His reply was to put his hand on my head and push me down onto his cock. I was almost too late, he came as soon as I took him in my mouth, it tasted so good too. I sat up quickly looking around to see if any other than the guys I was with saw and it all seemed good.

I told Chris I needed to go to the bathroom to touch up my make up. On my way I looked back they were all staring at me as I walked away. I came back out and told Chris It was time to go and he agreed but wanted Steve to comeback with us. I refused at first but relented when he told me he had already talked to him and he had agreed that he couldn't get any pussy just mouth and ass. We got up and all left together.

When we got back to my apartment Chris and Steve wasted no time getting naked as I went and slipped on a lacey nightie. I walked up to them got on my knees and started sucking one then the other. They were both moaning so loud I thought the neighbors would here. Chris wanted me to stand up so they could see my ass. I did as he said and they both began to rub and squeeze my ass as I wiggled with anticipation of what was to come.

Steve sat down on the couch so I got between his legs and took him in my mouth as Chris came around behind me. I felt him massaging my ass as he lifted my nightie then his cock pushed against my ass. He was in me bareback, a feel I love. After a few minutes he asked Steve if he wanted to fuck me and he said hell yea.

Steve has a long skinny cock but it felt nice in my ass. Chris came around and started fucking my face. I was in heaven living out my dreams. I felt Steve tense up and then his hot load shot into my ass. He pulled it out and shot more on my butt. Then Chris told me to get on top of him so I climbed on and slid down on his hard cock he reached under my nightie and started to stroke my cock. I was worried that Steve would see what he was doing and tried to stop him but he kept going. Steve was right there and did see but didn't even hesitate and joined Chris by reaching in and stroking my cock too before leaning over to take it in his mouth. Steve said He had never sucked a cock before but that he also never seen such a pretty girl with a nice hard cock to play with.

The three of us stayed together all weekend and they wore me out. Chris flew out Monday morning and Steve and I took a shower together getting in one last fuck before heading back to the ship. Chris came to visit twice and I went to Vegas to visit him once we had great sex every time and he always treated me like a lady, Steve left the navy a month later but managed to fuck me a few times before going home to Oregon.

Not long after all of that I met my future wife and didn't really play much for some time after that until she caught me wearing one of her dresses. That opened a whole new chapter for both of us.

  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Terri Goes on a Date

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 499 milliseconds