Written by tslover555
15 Jan 2012
first time out dressed.
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5 minute read
ive been crossdressing for years but tonite fir the first time i decided to get dressed and go for a drive. i started with usual shower, shaved all my body hair. i shud add im very slim with very long legs and if i do say so myself very convincing when dressed. anyway after shower and shave i pulled on my best black seamed ff nylons attached them to my 8 strap suspender belt, then pulled on my black lace thong and matching bra, then my sexy little black mini dress finished off with black 6 inch stiletto heels. then done my makeup before finishing sll off with my long black wig. had been chatting to a transvestite on another site who suggested i shud go out for a week and feel the air on my legs. i wasnt sure but after a bit of persuading she said if i wanted she wud keep me company so i agreed. we both agreed to meet half way in a lovely little country park calked peatlands . gates closr early so have to park at road and walk in. i arrived first very nervous ther was no cars so i got out and walked on in. it did feel great feeling the cool air on my nylon covered legs and blowing up my dress and i felt very sexy struttin in my heels. anyway after couple hundred yards i sat on a picnic table. and jenny txt to say she was at gate and wud b in in a minute so i told her where i was. 5 mins passed and i cud hear her heels clicking. we greeted with a peck on cheek as it was first time we had met but had chatted online for months. she looked amazing. she was wearing a long black coat down below her knees and white stilettos and from wat i cud make out she had nylons on aswell. anyway we went for a nice long walk 2 gether and chatted away it wasnt long before the subject turned to sex. she asked if i had ever been with another transvestite i said no ive only bern with woman. she said wud i like to be with anither transvestite. i said i wasnt sure if it was my thing i did admit that i did fancy her all dressed up with her make up on but wasnt sure if cock was my thing i never really considered myself as gay. with that she pushed me against the wall of the toilets and kissed me on my lips she asked did u enjoy that i said yes so she kissed me again this time puttin her tongue in my mouth and snoggin me and asked if i liked i said yes. she kissed me again only this time as my eges wer closed she kissed my neck then my chest. then i felt her hands lift my dress and pull my soft cock
out of my thong she kneeled in front of me and put it in her mouth and started sucking me off at this point i was anyones and wasnt long before i was hard. she turned me round bentnme over and licked my asshole and bslls while pullin me off wasnt long til i was cumin she sensed this and turned me round and sucked til i came in her mouth. she then asked if i enjoyed that i told her it was amazing she then said it was my turn. bein so horny i thought y not ive went this far anyway so i dropped to my knees and nervously took her hard cock
out and stroked it. input it to my lips and licked the tip it tasted good so i put it in my mouth and slowly sucked the full length of it tryin to copy wat she done to me. soon she put her hands on my head and started fuckin my mouth before pumpin 3 big spurts of cum in my mouth. i swallowed my first load of come and told her it was nice. she suggested we sat down gor bit on picnic table. so we sat and kissed some more and stroked each other nylon covered legs when she asked if i ever had anything in my ass which i said no apart from my finger the odd time. she asked wud like to try which i said i wasnt sure so she said did i want to fuck her ass. i wasnt sure but she sucked me hard and put a condom on my cock and put some lube on her ass snd bent over the table so i linrd up my cock snd pushed it into the first ass i had ever fucked it felt good. i started off slow but soon jenny was moaning and said harder so i picked up the pace but wasnt long til i had come i was to excited by it all. she turned kissed me and told me to get her hard i didnt argue i sucked her for 5 minutes then she put a condom on i said i wasnt sure so she said if it hurt she wud stop so i turned and bent over the table and felt her apply a lot of lube to my hole then 1 finger for a bit then 2 fingers then 3 then i felt the head of her cock at my hole she gently pushed it in then stopped it was sore at first bet then i relaxed she slowly moved it in and out til i loosened up a bit then started thrustin in harder i had never felt a sensation like it i loved it. soon i was moanin fkr more and even asked her to fill my virgin hole which she did. anyway we tidied up and walked back to car kissin and gropin on the way so i asked her if she wud like to come to mine which she agreed so she followed me home. and as im writing this she is asleep in my bed. if i have my way we will b spending all day fucking. if anyone wants to know wat happens 2 day just ask.