First time with a guy

I had been dressing privately for a number of years and never been with anyone while dressed up. That is, until I discovered this support group for other CD/TV and TS girls. I joined the group, which held meetings once a month about 40 miles from where I lived. I quickly made some friends and after the first meeting Emily asked if I wanted to go to the local gay bar and hang out. I had never been to a gay bar before, or even out dressed other than the meeting site.  There were about 12-15 of us “girls” at the bar and we had taken over 2 or 3 tables and just talked and got acquainted. I quickly became friends with Terri, and we always talked at the meetings. One night she asked if I wanted to come back to her room at a local motel, and to my surprise I did. I was shocked when she kissed me as we sat on the bed, I had played with a guy once in high school, just mutual masturbation, but had never kissed another person of the same sex before. Anyway, she introduced me into the bisex lifestyle that night and I found it to be amazingly erotic and sensual. But Im getting ahead of myself here, this story is about meeting a guy, not another girl.

About 2 months later, I was back at the bar with all the girls, just hanging out. I was dressed to the nines as usual, I wore a tight pink sweater that accented my 38 D silicone falsies, a tight black mini skirt, black thigh high stockings with lace at the top, a red garter belt, and pink lacy bra and matching thong, along with my 4″ open toe pumps. My makeup looked great also, with false eyelashes and of course bright red lipstick. All of this over a completely shaved body. I also wore my long blonde wig, which was a favorite of mine. A splash of femmy perfume completed me. And if I could, I would’ve picked myself up. I was feeling so very feminine.

Terri wasn’t there this month as she had to be out of town, but I was well liked by everyone and just hung out with everyone and loved sharing girl talk. We were taking turns buying drinks and when it came my turn to buy, I got up and tugged at my tight mini skirt so as to not show my lacy stocking tops, walked up to the bar and hearing my heels click on the hardwood floor was a turn on. I stood at the bar and tried to get the bartenders attention in my most feminine voice, which doesnt quite cut it. Just then I felt a hand on the back of my waist, just barely above my ass and turned to see a nice looking gentleman standing beside me.

He said his name was Jim and I gave him my long nailed hand and said, “I’m Lisa”.  “So nice to meet you Lisa, can I buy you a drink?” I explained that I was buying a round for my friends, and he offered to buy the round. I accepted and he helped me deliver the drinks to the table, just as a slow song was being played by the DJ. I was about to sit down, when Jim put his hand around my waist and asked me to dance.  I grabbed his hand and we walked to the dance floor. It felt so great to feel his arms wrapped around me, holding me tight. I stand 6′ tall in heels and he was taller than me, made me feel so much more like a woman.  I felt so at ease as he pressed tightly against me, with his hands cupping my ass, feeling his manhood press against my tummy. I wanted to drop to my knees in front of him right there on the dance floor. I wanted a real man that night, a masculine man to make me feel like the woman I wished I was. Then he kissed my neck and told me how incredibly sexy I looked and how glad he was that I was wrapped in his arms. I replied with, “what a wonderful thing to say”, as I looked into his eyes and smiled and then he kissed me, his tongue finding mine and swirling around in my mouth.

Jim suggested we get out of there and I was more than happy to agree. I explained that I lived 40 miles away and had a wife at home so that wasnt an option. He said he lived alone, about 10 miles from the club. I said goodbye to the girls, who wished me a good night and walked arm in arm with Jim to my car, knowing it would be a great night. Jim kissed me at my car and told me to follow him. My clitty was getting hard as I drove, knowing the night ahead would be awesome.

We arrived at Jim’s apartment and walked into his home with his hand planted firmly on my ass. He kicked off his shoes, turned the fireplace on and told me to make myself comfortable. I asked where the powder room was, and I excused myself to freshen up, applying more lipstick and checking myself out. I returned and Jim was sitting on the couch with 2 glasses of wine. He caressed my legs and up the inside of my skirt as I sat beside him. Then he kissed me as he explored up my skirt, finding my lacy thong and my now hard clit. I reached over and squeezed his bulge and discovered he was equally as hard, and from what I could determine bigger than me. Much bigger. We made out like teenagers there on the couch and I fumbled as I tried to undress him. His chest was hairy and I ran my long fingernails thru his hair, and then undid his jeans. I slid my hand inside his jeans and was pleasantly surprised to feel his hard cock, which had to be close to 9 inches, not too thick, but not thin either. I ever so gently slid my hand up and down his shaft with a light feather touch, this made him moan loudly, which only encouraged me more. He was so much bigger and harder than my friend Terri, and I wanted to taste him as I had done with Terri just twice before. I looked into his eyes as I leaned over and my lips met the tip of his cock. I heard him moan as I licked the tip and was rewarded with a sweet taste of pre cum. “Oh, Lisa, that feels so good” he said. His fingers were in my hair as I parted my lips and let his cock slide into my warm, waiting mouth. My tongue was pressed firmly against his shaft as I slowly took more and more of his cock into my mouth until I was about an inch from the base. His manly aroma wafted into my head and I knew then and there that this was the person I was meant to be.  He put his hands on my head and began thrusting upwards into my mouth. “oh yes, suck my cock Lisa”. Feeling him fuck my mouth and hearing him moan and talk to me only turned me on more and my hard clitty was now dripping pre cum on its own. I continued to stroke his cock with my bright red lips as I cupped and teased his balls. I had never tasted Terri’s cum, but I really wanted it from Jim. After a few minutes of enjoying his cock, his body began to tighten up, his cock was pulsating on my tongue, he was grunting and I knew I had brought him to the point of no return. And then it happened, he exploded with what seemed like a gusher of warm creamy man cum into my mouth and down my throat. I squeezed his balls gently wanting it all. Some of it dripped from the corner of my mouth and I quickly sucked it back in, enjoying the taste and texture of this hot man. When I had swallowed it all and felt him go limp I came off and sat up and smiled at him. Jim smiled back at me and placed a hand behind my neck, pulled me to him and kissed me deeply and passionately. Then he went down on me and returned the favor until I too was drained and limp.

We sat there and talked into the wee hours of the morning. I explained how my marriage was stale, how my wife knew I dressed, but she hated me doing it, and how I was still new to the bisexual lifestyle with Terri, and my wife was unaware of that about me, but seeing as the marriage was practically over, it didnt matter. He said he was divorced and bisexual, had always been attracted to girls like me and how its been the best sex of his life. I said I would have to agree, so far. He asked if I like to bottom, and I explained that I never have, but I feel very comfortable with you and would like to explore. Then he asked me if I would like to spend the night with him. I agreed and went to the car to get my boy clothes for when I leave the next day. I went back in, asked to use his phone (this was before cell phones) and called my wife, told her I wouldnt be home that night. Her response was to not come home at all, that she had met a guy while out at the club with her girlfriends. I then told her I had done the same and he is great. I explained I would be back the next day for my things. I asked Jim if I could stay with him for a couple of days just until I find an apartment of my own. He said that would be just fine, and we climbed into bed together, where he proceeded to introduce me to anal sex and fucked my brains out.

To be continued…..

VN:F [1.9.22_1171]
Rating: 8.4/10 (19 votes cast)
VN:F [1.9.22_1171]
Rating: +1 (from 1 vote)
First time with a guy, 8.4 out of 10 based on 19 ratings

Leave a Reply

You must be logged in to post a comment.