I've Done It Once

Yay for me!!! Okay so the story is as follows.  I met up with a guy through craigslist, and although i have plenty of panties and fun girlie cloths myself he said he had a bunch of lingerie that his ex-girlfriend didn't take with her.  So i decided i would wear what he had for me.  When i got there he wasn't in the best shape and probably like 13 years older that me but i really wanted sex, so we talked for a little bit, i was nervous mind you cuz i haven't really ever done this before, then i finally said "so...do you have any cloths for me to wear" and he smiled and chuckled saying "you get right to the point don't you, you little ****."  and i smiled and nodded my head.  We went to his room and he pulled out a laundry basket (he had just washed them for me how considerate) and said "I want you to suprise me"  So then he went back to his living room to watch whatever game was on the TV while i looked through the cloths.  Eventually i picked out a little corset type thing and a lepord print thong that didn't match but still kinda covered me up, albeit a little but it was good!  So after i was feeling confident i opened the door and walked to the living room and stood there in my corset and panties smiling.  "Do you like it!" i said bouncing.  "Yeah, spin around and lemme see your ***!" so i showed him my *** and he had a grin on his face that let me know what was coming.  I said "do you want to move this to the bedroom?" "hold on **** i wanna slap your *** first" and he stood up and walked over to me clutching my *** then smacking it.  After that good smack he walked over to the bed taking his cloths off, he was out of shape but i had promised in my emails to be a little **** for him so i just focused on the fact that he had a penis and it was my job to get it off.  "Okay **** suck me off"  I needed no more instructions than that i crawled on the bed and began to suck his **** while i played with his balls,  sometimes i would use my hand to jack him off while i sucked him.  Also sometimes he would put his hands on my head and press down, shoving his **** into my throat.  Then he told me "just use your mouth ****" so i put my hands on either side of his legs and began sucking as hard as i could.  Bouncing up and down, unless he held my head down.  Eventually he said "Okay **** i'm gonna **** your *** now"  My heart fluttered with anxeity and excitement, i had never had sex that way.  "Put your *** up in the air and rest your face against the bed" He said i heard him uncapping his lube.  I felt a finger trace my hole and slide in and out a little bit.  I was so nervous.  After he put a condom on he said "alright **** here it comes "  It slid into me and i gasped for air.  It really hurt and i asked him to slow down and he said very calmly "just relax you'll get used to it in a little while" and sure enough i did i soon was pumping my *** along with his thrusts and then he grasped my hips and pulled me down as far as he could go releasing his load.  Afterwards he got dressed and went back to his game, i undressed and changed back into my old cloths said thank you and left.

Thats my story, i really enjoyed it, and i haven't done anything like it for a while but i hope everyone enjoyed reading it.  I would totally do it again!

fornowish fornowish
22-25, M
11 Responses Feb 17, 2009

well that got me hard.......and rubbing

It'd be nice to find a local sissy I could hook up with for fun times like you had! Of course, they seem to be hidden. So it goes...

I envy you !

To answer your question he had some stuff that belonged to his ex but for some reason he still had them, though i have plenty of cloths for myself too! Usually when i see him which has only been 2 times i wear what he has cuz i don't have access to it on a daily basis, but the 2nd time i saw him i wore my cloths because he hadn't seen them and i wanted to surprise him

I love your story! it really got me warm inside, but i have to ask: Did you took the clothes with you? or anytime you want to wear them you have to go there to pick them? ;)

Sounds like a good time. As long as your with someone who appreciates and respects you, you're bound to have a good experience. Anyway, sometimes it's tough to find people in NYC. You did well.

I just posted my second encounter with this man to this group if you want to read it, i'm glad you enjoyed the story!

good luck

Thanks for the comments everybody, i'm going to give the guy a call this weekend and see if he wants to do it again!!!!

great story, fornowish thank you for sharing it. i enjoyed it very much .

Wonderful story. It made me reflect on some of my experiences, and I think that maybe sometimes as sissies we get to realize just exactly what it is that women have been saying about men forever, crude and basic. Slam, bam, thank you mam, little foreplay, little compassion. Sex with another sissy is so much better.