My first time with a man

Anal

My first time with a manI had been dressing privately for a number of years and neverbeen with anyone while dressed up. That is, until I discoveredthis support group for other CD/TV and TS girls. I joinedthe group, which held meetings once a month about 40 milesfrom where I lived. I quickly made some friends and afterthe first meeting Emily asked if I wanted to go to the localgay bar and hang out. I had never been to a gay bar before,or even out dressed other than the meeting site. There wereabout 12-15 of us “girls” at the bar and we hadtaken over 2 or 3 tables and just talked and got acquainted.I quickly became friends with Terri, and we always talkedat the meetings. One night she asked if I wanted to come backto her room at a local motel, and to my surprise I did. I wasshocked when she kissed me as we sat on the bed, I had playedwith 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 thatnight and I found it to be amazingly erotic and sensual.But Im getting ahead of myself here, this story is aboutmeeting 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 worea tight pink sweater that accented my 38 D silicone falsies,a tight black mini skirt, black thigh high stockings withlace at the top, a red garter belt, and pink lacy bra and matchingthong, along with my 4″ open toe pumps. My makeup lookedgreat also, with false eyelashes and of course bright redlipstick. All of this over a completely shaved body. I alsowore my long blonde wig, which was a favorite of mine. A splashof femmy perfume completed me. And if I could, I would’vepicked myself up. I was feeling so very feminine.Terri wasn’t there this month as she had to be out oftown, but I was well liked by everyone and just hung out witheveryone and loved sharing girl talk. We were taking turnsbuying drinks and when it came my turn to buy, I got up andtugged at my tight mini skirt so as to not show güngören escort my lacy stockingtops, walked up to the bar and hearing my heels click on thehardwood floor was a turn on. I stood at the bar and triedto get the bartenders attention in my most feminine voice,which doesnt quite cut it. Just then I felt a hand on the backof my waist, just barely above my ass and turned to see a nicelooking gentleman standing beside me.He said his name was Jim and I gave him my long nailed handand said, “I’m Lisa”. “So nice tomeet you Lisa, can I buy you a drink?” I explained thatI was buying a round for my friends, and he offered to buythe round. I accepted and he helped me deliver the drinksto 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 waistand asked me to dance. I grabbed his hand and we walked tothe dance floor. It felt so great to feel his arms wrappedaround me, holding me tight. I stand 6′ tall in heelsand he was taller than me, made me feel so much more like awoman. I felt so at ease as he pressed tightly against me,with his hands cupping my ass, feeling his manhood pressagainst my tummy. I wanted to drop to my knees in front ofhim right there on the dance floor. I wanted a real man thatnight, a masculine man to make me feel like the woman I wishedI was. Then he kissed my neck and told me how incredibly sexyI 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 happyto agree. I explained that I lived 40 miles away and had awife 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 tomy car, knowing it would be a great night. Jim kissed me atmy car and told me to follow him. My clitty was getting hardas I drove, knowing the night ahead would be escort güngören awesome.We arrived at Jim’s apartment and walked into his homewith his hand planted firmly on my ass. He kicked off hisshoes, turned the fireplace on and told me to make myselfcomfortable. I asked where the powder room was, and I excusedmyself to freshen up, applying more lipstick and checkingmyself out. I returned and Jim was sitting on the couch with2 glasses of wine. He caressed my legs and up the inside ofmy skirt as I sat beside him. Then he kissed me as he exploredup my skirt, finding my lacy thong and my now hard clit. Ireached over and squeezed his bulge and discovered he wasequally as hard, and from what I could determine biggerthan me. Much bigger. We made out like teenagers there onthe couch and I fumbled as I tried to undress him. His chestwas hairy and I ran my long fingernails thru his hair, andthen undid his jeans. I slid my hand inside his jeans andwas pleasantly surprised to feel his hard cock, which hadto 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 lightfeather touch, this made him moan loudly, which only encouragedme 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 twicebefore. I looked into his eyes as I leaned over and my lipsmet the tip of his cock. I heard him moan as I licked the tipand was rewarded with a sweet taste of pre cum. “Oh,Lisa, that feels so good” he said. His fingers werein my hair as I parted my lips and let his cock slide into mywarm, waiting mouth. My tongue was pressed firmly againsthis shaft as I slowly took more and more of his cock into mymouth until I was about an inch from the base. His manly aromawafted into my head and I knew then and there that this wasthe person I was meant to be. He put his hands on my head andbegan thrusting upwards into my mouth. “oh yes, suckmy cock Lisa”. Feeling him fuck my mouth and hearinghim moan and talk to me only turned me on more and my hard clittywas güngören escort bayan now dripping pre cum on its own. I continued to strokehis cock with my bright red lips as I cupped and teased hisballs. I had never tasted Terri’s cum, but I reallywanted it from Jim. After a few minutes of enjoying his cock,his body began to tighten up, his cock was pulsating on mytongue, he was grunting and I knew I had brought him to thepoint of no return. And then it happened, he exploded withwhat seemed like a gusher of warm creamy man cum into my mouthand down my throat. I squeezed his balls gently wantingit all. Some of it dripped from the corner of my mouth andI quickly sucked it back in, enjoying the taste and textureof this hot man. When I had swallowed it all and felt him golimp I came off and sat up and smiled at him. Jim smiled backat me and placed a hand behind my neck, pulled me to him andkissed me deeply and passionately. Then he went down onme 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 Idressed, but she hated me doing it, and how I was still newto the bisexual lifestyle with Terri, and my wife was unawareof that about me, but seeing as the marriage was practicallyover, it didnt matter. He said he was divorced and bisexual,had always been attracted to girls like me and how its beenthe 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 neverhave, but I feel very comfortable with you and would liketo explore. Then he asked me if I would like to spend the nightwith him. I agreed and went to the car to get my boy clothesfor when I leave the next day. I went back in, asked to usehis phone (this was before cell phones) and called my wife,told her I wouldnt be home that night. Her response was tonot come home at all, that she had met a guy while out at theclub with her girlfriends. I then told her I had done thesame and he is great. I explained I would be back the nextday for my things. I asked Jim if I could stay with him fora 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 fuckedmy brains out.

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