first time cumming

When I was 12 I began secretly stealing my s****rs pills and clothing and make up, I was dressed up as a girl when I was younger and enjoyed the feeling so growing up I have always had a time to connect with my femme side, when I started stealing her clothes and make up I would look up videos online to see where all the make up went and what was good colors for my complexion, I've always been pretty skinny but the last year I let myself go and put on a few extra pounds and began to fill in the bras and panties a lot better than usual. After noticing how great it felt I began to diet again but this time, I worked out certain parts of my body, I would wear training bras under my beaters and t shirts, I would wear women's work out gear basically everyday I would jog and work out, and by the way, my way of working out was on a workout ball, leg lifts and other girl things, I gained quite the womenly figure after about three months and shed a very good amount of weight... Around this time I began shaving my head and buying wigs I never had liked my real hair so it just seemed natural for me. I would jog on the treadmills at the gym and do all the other workouts in the comfort of my home, I didn't want any extra attention from anyone because it wasn't worth it to be used and also I didn't think I liked the type of people who would check me out, I mean of course men. I would tell myself all the time I'm not gay and I believed in my heart that I wasn't, not even slightly bisexual but that changed quite drastically when I saw my new workout buddy.. he walked in to the locker room and stood in the opposite row of lockers and began to undress I looked at him and saw a beautiful women, curvy sexy blonde, luscious lips, big round bubble butt and best of all, a nice set of titties... I was confused so I said you got the wrong room beautiful... He turned and with a sultry voice he said, maybe after my surgery... But I'm all man honey, from the looks of it you should be coming to my side too soon and with that we began talking quite regularly, I enjoyed his company we would workout together and go out to eat, he even came back to my apartment a few times and we would kick back on my couch and just watch movies together, it all kind of just changed one day when I went into the locker room one day and saw him fully nude. He was all women except for the big uncircumcised cock dangling inbetween her thighs, I gasped and looked at her eyes and with that we began to laugh and we worked out and went back to my place like normal I don't know what It was but ever since I had saw her cock I've been horny, so when we got back to my place I asked if her whole situation had started with wearing her s****rs or someone's clothes at a younger age and exactly how she identified herself she explained that she was intact involves with a boy when she was younger and would dress up in girls clothes and give the boy head when he wasn't even able to ejaculate it really changed her outlook on life and sealed the deal for her, I told her about how I like to dress up and share the same gender misidentity, she cut me off and said its not a "misidentity" its what you are own it. And with that I apologized and asked if I could try to please her, with that she barely hesitated and began to pull her pants down. I have never touched another man's junk before but I had caught myself checking other girly boys out before and I always enjoy curves and their junk, booty is my favorite part of a girlyboy... Anyway she didn't even play with it or anything just handed me it and told me to kiss her first so I did and as we kissed she embraced me quite quickly and we kissed for Atleast 5 minutes just making out as I stroked her cock and felt on her female exterior. We both knew what we wanted and we were both ready to take and receive. So I took my tongue off of hers and embraced her small nipple between my tongue and lip and began massaging it and continued to play with her clit as I slowly grabbed down at my pants to adjust my crotch, she grabbed my head with both hands and began to motion me down so I obediently listened and began to lick at the skin at the tip of her cock that cover her entire penis I stroked her for awhile and slowly pulled back the foreskin until I had a fully form cock head between my lips I enjoyed the feeling of sucking and licking and mouthing at her cock in anyway I could to try to find a way to get her to feel good, I bobbed and sucked and made a few pop noises, if we were recording it we could've sold it to a porn studio and made a lot of money it was hot I blew her for a good ten minutes until she finally made me stand up and began to undress she motioned for me to go find a set of white bra and panties which I had many of, so I went into my backroom found some clothes and decided to wear a little more for my manly sissy sexy Slut so I toss on a wig and do my makeup pretty quickly I got into a good routine, I put on black and silver eye shadow with some cover up to curve my cheeks more femme and added lip plumping and lipstick along with stuff to make my kisses taste good, after that I tossed on the bra and panties and began to find the right dress I found it! I screamed quietly and pulled it up it felt really tightly but it was a body hugger and it was meant to stretch, I already had some rose peddled knee highs on and a sexy little outfit on under it I looked good and felt good, I double checked my make up and grabbed a pair of heels and tossed them on strapping them up and walking out the door way I noticed a pair of shoes by the door were missing, I looked around the corner and noticed she wasn't in my livingroom anymore I tried to call her phone and it rang twice and she answered, I asked where did you go? She said she would explain in twenty minutes she said to get comfortable and put on some good music and don't play with myself or go anywhere stay in the bra and panties for her, I was so excited I didn't care why she left I was just waiting for her return. She slowly slipped back in without me noticing about five minutes later I was fixing us glasses if champagne and she just laid on the couch and began to stroke herself I finally walked into the livingroom and she gasped and said Jesus you are gorgeous... I blushed and said the same, she said I am gonna change in your room okay I have a surprise for you. She went into my room and made some noise I couldn't hear to well over my crazy heartbeat but it felt great to be with someone. Anyway she finally walked in the room fully dressed up and gorgeous stunning she was in domme leather and had a bag of toys she said she likes to use.... I explained I had never done anything sexual other then with a regular woman and had no idea where to start. She walked over to me and began to kiss deeply, she slowly pushed me onto my couch and laid me back where she pulled out my cock and licked it and sucked it for about three minutes and I came and she swallowed all of it I told her I'm gonna cum and she pulled out and said feed me before diving back down and sucking every drop of it out of me... I couldn't believe how great she was I came so hard it was unbelieveable... I caught my breath and she said it was my turn bend over and lean on the couch. I did as told and she hiked up my skirt bottom and pulled my panties to a side and grabbed a small bottle of ky and began fingering at my hole, the sensation alone made me moan uncontrollably. I enjoyed it never had done anything like this before not even a finger had been there before. she could tell I wasnt used to it so she pulled out a toy about half as big as her cock and probed my tight hole with it and I moaned and it hurt a little bit but it quickly began to feel good and she sensed it so as quick as I got comfortable I was empty she began to lather up her cock and slowly edged him in I moaned again and so did she. I reached down between my kegs and cupped my dick and balls which were completely soft and limp but the second I got comfortable on her stick again my little clitty began to stiffen up and my balls got tight... I enjoyed what was happening to me I was being fucked like a girl and I was moaning and dressed like one too. It was heaven and as she slowly stroke in and out and upped her pace I began to feel a sort of tense feeling in my clit I began to feel a pressure build up and slowly I began to feel an eruption upon me.. as she stroked in me with a quick stride each time now me being so near, it was inevitable.whatever it was, was gonna happen now and I said something along the lines of, I think... And it haooened... My cock let out load after load of cum and I cried and moan and shook and tightened up my hole as I orgasmed for the first time from anal sex....
100% (14/0)
Posted by reefermcrevolver
2 years ago    Views: 610
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1 year ago
Great story! Loved it!