My Journey to Becoming a Sissy

It all started years ago with an ex girlfriend, Karen. She was very good looking, and had a big sexual appetite. She'd like to dress very seductive in lingerie, which really turned me on! Sensing that, she'd exploit her sexuality and rub up against me in her silky or satin outfits making me so hard till I thought I'd explode. The feeling of her rubbing and grinding that cute little panty cover ass on my hard cock was too much and I would sometimes cum just from that. She would also wrap my cock with a pair of her panties and stroke me until I would cum all over them, only watch her lick the panties clean. One night it progressed to her having me try on a pair of her panties. On the outside, I was like "No way baby, I ain't that way" but on the inside I was like "Hell yeah, give me those panties!" I made it sound like she talked me into it, and slipped them on. I'll never forget the way they made me feel, my cock sprang to attention so fast, and was the hardest it has ever been. She gave me the best blow job I've ever had that night, I stayed hard and we began to make love with my cock sticking out of the panties that I was still wearing.
The next day she had an idea that we go shopping. Seeing how I was so turned on by wearing panties, and the sex was amazing, she thought it would be fun to get me some of my own. She had me slip into another pair of hers and we went to Macey's. I was so hard from the satin paties I was wearing plus the excitement of shopping for me, I could hardly walk with my stiffy trying to bust out of my jeans. Once we got to the intimate section, she would hold up different pairs in front of me and say how cute they are and she couldn't wait to see me in them. There were other ladies around along with the salesclerk, and I know they heard what she said. Boy did we get some looks, some put off, others had a slight approving smile. It was embarrassing to me. Once we made it back home, she had me do lingerie show for her. Panties with matching bras and satin teddys with matching thongs. I was experiencing feelings like never before, and I liked it! The sex was intense, I liked wearing the outfits as much as she liked the feeling of them on me while were banging like crazy. It wasn't long before I was wearing panties all the time. She would come home with a new outfit from time to time so I lnow she liked what they did for me.
One night she brought home a co-worker, Shelly, for dinner. She works with Shelly at the bank. We had a nice dinner and a couple bottles of wine then Karen asked Shelly if she wanted to know a secret. I thought she was going to gossip about another girl from work, but oh no, she went on to explain how I like to dress up in ladies frilly panties and lingerie, that I have a whole dresser full of it, and is wearing some now. I was embarrassed and pissed at the same time. I couldn't believe she betrayed that trust!
Shelly had a little shy grin on her face, and said "oh, I'd love to see that." I was getting hard thinking of the fact that I was caught, what to do, what to do...
I was humiliated when the two girls went to the bedroom to check out my collection. I could hear them giggling and Shelly saying over and over how she would like to see me in this outfit or that. Karen told her she would before the night was over. One more bottle of wine and I was getting more comfortable with the idea. I've known Shelly for a while through Karen but not really all that well. I told them I would agree to strip off my outer clothes if they would do the same. They agreed, and we all stripped down to our bras and panties. Shelly looked amazing, she must spend a lot of time at the gym. I was of course hard as a rock, leaking pre cum so my light pink silk panties are beginning to become see through, not that there's much left to the imagination. I felt so exposed. Karen ask Shelly if she wanted to rub it, she did and OMG I thought I would cum from that. She then pulled them down a little and reached in and pulled out my throbbing cock, she licked the pre cum off my head and started to work her lips and tongue up and down my shaft, mixing her saliva with my pre cum, getting me so wet and slick. Karen, meanwhile is a chair watching the whole thing massaging her puffy clit. Shelly takes a break from my cock and starts to lick and eat Karen, so fucking hot. I walk to Karen, put my cock in her face so she can continue sucking me. Shelly must really good at eating pussy because Karen can't concentrate so I walk behind Shelly, slide her little thong to the side and begin to eat her pussy too. After she's dripping wet I plow my cock deep inside her moist hot pussy doggy style. Thrusting in and out has her, she's hitting Karen's clit in the right spot and she cums, bucking and moaning as Shelly keeps licking and sucking her clit. That's too much for me, and I let go with streams of cum inside Shelly and on her back. Karen returns the favor and eats out Shelly until she cums hard.
We've had other encounters with Shelly, and also other girls from the bank. I'm getting more comfortable with girls seeing me dressed up in lingerie. I guess my secret is really not a secret at all, at least not at the bank.
Then one night she had me meet Marla. A stunningly beautiful, tall brunette with an absolute smoking hot body. She came by in a short yellow skin tight dress, black thigh high stockings and heels, but not too high. She had turned me on from the first sight. Over dinner Karen and Marla would share glances at each other then smile, giggle and look away. I'd ask what was so funny, but they just would say it's nothing. After dinner and wine, feeling good, Karen asked if we wanted to play a game. I was up for anything as long as I would have a chance to play with Marla. She said that we should all put on blindfolds then see what happens. I thought that sounded kinda kinky and fun, so I was all in. We all get a spare dinner napkin for blindfolds, get on the floor and put them on. Now we have to find and help another get out of her clothes. As luck would have it, I found Marla, she unbuttoned my shirt, noting my bra, and undid my jeans. I then unzipped her dress from behind, dying to see that body. She began to kiss me and caress my panty covered ass, and I rubbed her little sexy ass. She pushes me back on the floor, and I can tell she's turned around so she can gain access to my cock, and I can feel that she's lowering herself to me. I'm getting ready and anticipating her sweet pussy any second to be positioned for my outstretched tongue. Then I hear Karen whisper in my ear "let your inhibitions go baby". I'm thinking, what inhibitions? I'm laying here blindfolded wearing a bra and panty set, while a complete stranger dress the same is about to suck my cock as I eat her pussy. I raise my head to meet her crotch, stick out my tongue and notice, that's not a pussy inside that thong, it's a cock!!! What the fuck is going on? All the little giggles and glances makes sense now, this was all planned. Marla reaches down to pull out my cock, and starts giving me a fantastic blow job. Maybe it was the wine or the fact I'm feeling feminine dressed the way I am, or the "training" Karen has put me through, but at that moment, all I wanted to do was suck Marla's cock. I reached up and released it from it's panty and began giving my first blow job. It was exhilarating, feeling her getting harder in my mouth, the taste of her pre cum was so good. I wanted to see so I took off my blindfold and Karen had a huge dildo and was riding it hard. Marla was sucking my cock up until the point of me cum. I pulled away just in time. If I was going to be one of the girls tonight I wanted to experience it all. Karen's dildo was all wet from her pussy juice, so I begged her to fuck me with it. As Marla lay on the floor, I continue sucking her cock as Karen pegs me with that dildo. I feel like such a slut! Not sure how much time went by, I'm enjoying getting fucked in both holes. Marla holds my head as she fucks my face, then I feel her tighten up, short thrust in and out and a wave of cum released from her cock fills my mouth, it's so much that I can't hold it all and it runs out of my mouth down her shaft. Karen sees this and immediately joins me licking and sucking her cum off her cock and balls. Marla takes another turn sucking my cock while I eat Karen, Karen soon cums grinding my head into the floor almost. Not long after I fill Marla's mouth with my cum. Once I finished with the last pulse she shows me her mouth full of my cum, then her and Karen begin to swap cum kisses. One of the hottest things I've ever seen.
Karen then started to suck on Marla, getting her nice and hard. Marls mentioned how much I liked getting fucked with a dildo, and how about the real thing since you're one of the girls tonight? I don't know what hold those girls had over me that night, but I was in! She positioned me on the floor on all fours, then gently slid her slick hard cock inside me from behind, little by little until she had it all in. slow and steady at first, then pick up the momentum, my balls swinging to her passionate fucking. My cock now hard and leaking pre cum. Karen lays down under me and as Marla thrust forward Karen gets her faced fucked by my cock. This feeling is insane! I'm going to cum by getting fucked in the ass! I unload all over Karen's face, my boi pussy tightening with each pulse sending Marla over the edge and she cums inside me. I hold that position as Marla pulls out, I can feel the cum start to leak from my boi pussy down my balls. Karen gets up and licks the cum from my balls and as it runs from my hole. I can't believe what just happened to me, and can't wait to do it again.
Karen and I had many more play dates with Marla, until we split up. I started seeing Marla full time then. I still like pussy, but I LOVE cock!
Opublikowano przez slipn2panties
1 rok temu
Komentarze
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redclay56
THAT was a hell of a yarn!
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Nice Hot Sexy Story
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Very hot!
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slipn2panties
do zeenacd2 : Mmmmmm glad you liked it!
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zeenacd2
made me cream my panties
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SancheZ069
do hotdogger34 : this story got my cock hard as well
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SancheZ069
so hot :smile:
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Moreticiacokx
Lucky fucker
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Super story 
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SancheZ069
Hot :smile:
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outstanding story my cock so fucking hard as i read this
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ExoticSmallTits
Hot story!
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MissLesley
Wonderful -would love to have been you there
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sliplover
Well done, both in action and writing.  I, too, am rock hard reading it.
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pantiesboy65
Fucking awesome. I was rubbing my hard cock while I was reading this. Thanks for sharing.
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