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Old 03-09-2010, 02:33 AM   #76
spaceace76
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i love your post amy. I wish I could find someone like you that would just let me experiment for a night or two
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Old 03-09-2010, 06:01 PM   #77
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[quote=RagsNRiches;33521574]Amy,
Please post more; you are so sexy!

Last edited by amylin456 : 05-29-2013 at 06:47 PM.
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Old 04-22-2010, 10:23 AM   #78
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Nice ass and panties

Quote:
Originally Posted by amylin456 View Post
I have had a few people request a picture- so trying here:
My first experience began when I was in my teens, my parents were gone for the day and my step sister had just left to visit friends up the street. I went into my stepsister room and got into her panty drawer to find a pair of pink
string bikini panties. I put them on, of course my cock was already hard before I ever decided to put them on. Panties always makes my dick hard. I stood in front of her full length mirror to admire how I looked in these sexy panties. I started rubbing my cock. Boy was I in heaven feeling so sexy and horny. I proceeded to remove my cock from my panties and began to jack off, just then my stepsister came into the room and saw me jerking off with her panties on. She didn't seem to be alarmed,
she just asked me to lie down on the bed and she would take over. I laid down on the bed and she proceeds to lick the outside of my panties on my
7x5 cock. This was certainly feeling wonderful. She then pulled down my panties and gave me my first blowjob and letting me cum in her mouth. She
told me she had other plans for me in the future. Couldn't wait till next time. Been hook ever since wearing panties. They feel so sexy and makes my cock hard.
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Old 04-22-2010, 10:28 AM   #79
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So did you and your stepsister ever hook up again? She sounds like she really liked you in her panties.

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Originally Posted by lostinsex View Post
My first experience began when I was in my teens, my parents were gone for the day and my step sister had just left to visit friends up the street. I went into my stepsister room and got into her panty drawer to find a pair of pink
string bikini panties. I put them on, of course my cock was already hard before I ever decided to put them on. Panties always makes my dick hard. I stood in front of her full length mirror to admire how I looked in these sexy panties. I started rubbing my cock. Boy was I in heaven feeling so sexy and horny. I proceeded to remove my cock from my panties and began to jack off, just then my stepsister came into the room and saw me jerking off with her panties on. She didn't seem to be alarmed,
she just asked me to lie down on the bed and she would take over. I laid down on the bed and she proceeds to lick the outside of my panties on my
7x5 cock. This was certainly feeling wonderful. She then pulled down my panties and gave me my first blowjob and letting me cum in her mouth. She
told me she had other plans for me in the future. Couldn't wait till next time. Been hook ever since wearing panties. They feel so sexy and makes my cock hard.
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Old 04-22-2010, 11:00 AM   #80
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Re: Many encounters

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Originally Posted by Pittdude1972 View Post
So did you and your stepsister ever hook up again? She sounds like she really liked you in her panties.
My step sister and I had many more interludes. She enjoyed these meeting
as much as I did. Looking back on it i would do it again in a hardbeat.
I just took a shower and shaved my cock and balls, sitting here in some black
string bikini panties very similar to the first ones I ever tried on and my dick is
hard. I just told it out and am stroking it, some precum just came out and I
wiped it off with my finger and licked it off. Precum is delicious. Now thinking about what my stepsister and I use to do and stroking my cock at the same time.
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Old 04-22-2010, 11:13 AM   #81
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I agree with you...I'd have done it as many times as I could with her.LOL


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Originally Posted by lostinsex View Post
My step sister and I had many more interludes. She enjoyed these meeting
as much as I did. Looking back on it i would do it again in a hardbeat.
I just took a shower and shaved my cock and balls, sitting here in some black
string bikini panties very similar to the first ones I ever tried on and my dick is
hard. I just told it out and am stroking it, some precum just came out and I
wiped it off with my finger and licked it off. Precum is delicious. Now thinking about what my stepsister and I use to do and stroking my cock at the same time.
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Old 04-25-2010, 07:43 PM   #82
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Beautiful

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Originally Posted by amylin456 View Post
I have had a few people request a picture- so trying here:
Hi Amylin

Just wanted to tell you that this was one of the sexiest pictures I've seen in Lit.

Absolutely beautiful.

E
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Old 04-25-2010, 08:04 PM   #83
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My first experience was about 4 years ago. My girlfriend was out of town and i tried on some of her stuff. The only things i could fit in were the stretchy things but i enjoyed it. I eventually found a pair of panties and a bra that i could manage to fit in and an adjustable mini-dress and tube top. I also put on her makeup and lipstick. She was gone for a week so everyday i came home and dressed up and paraded around the house. At first it was just in the bedroom but then i got braver and opened the blinds and walked around the house. Soon i was sleeping in the lingerie.

I started noticing i was getting off on the idea of getting caught so i would do things like open the blinds and curtains and walk around or stand in a window for a few minutes. Eventually i got brave enough to try one of her old dildos on myself. It was a real skinny one and after some lube i got it in. I fucked myself with it in the bedroom and worked my way out to the living room. The day before she came home i decided to go all out so i got dressed up, opened the curtains blinds, and propped the front door open. Anyone could have just walked in (we lived in a subdivision). I laid face down in the living room floor, 2ft away from the open door, with my miniskirt rolled up on my hips while i fucked myself with the dildo. I came hard all over the tile floor and licked up every drop. That was the start of my bi-curious/humiliation/exhibition fetish.
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Old 04-25-2010, 08:06 PM   #84
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Originally Posted by amylin456 View Post
not the best , but heels are so much fun
I want to run my hands up those sexy legs so bad!
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Old 04-25-2010, 09:46 PM   #85
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Quote:
Originally Posted by Curious_Sub View Post
My first experience was about 4 years ago. My girlfriend was out of town and i tried on some of her stuff. The only things i could fit in were the stretchy things but i enjoyed it. I eventually found a pair of panties and a bra that i could manage to fit in and an adjustable mini-dress and tube top. I also put on her makeup and lipstick. She was gone for a week so everyday i came home and dressed up and paraded around the house. At first it was just in the bedroom but then i got braver and opened the blinds and walked around the house. Soon i was sleeping in the lingerie.

I started noticing i was getting off on the idea of getting caught so i would do things like open the blinds and curtains and walk around or stand in a window for a few minutes. Eventually i got brave enough to try one of her old dildos on myself. It was a real skinny one and after some lube i got it in. I fucked myself with it in the bedroom and worked my way out to the living room. The day before she came home i decided to go all out so i got dressed up, opened the curtains blinds, and propped the front door open. Anyone could have just walked in (we lived in a subdivision). I laid face down in the living room floor, 2ft away from the open door, with my miniskirt rolled up on my hips while i fucked myself with the dildo. I came hard all over the tile floor and licked up every drop. That was the start of my bi-curious/humiliation/exhibition fetish.
thats sooooooooo fucking hot
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Old 04-25-2010, 10:18 PM   #86
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Quote:
Originally Posted by amylin456 View Post
not the best , but heels are so much fun
Thank you,, I do like heels and nylons and..
http://forum.literotica.com/attachme...5&d=1272167287


http://forum.literotica.com/attachme...5&d=1271995533
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Old 12-07-2012, 08:52 AM   #87
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bump. any more stories?
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Old 12-12-2012, 03:59 AM   #88
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After a week or two, we continued to talk but our schedules weren't quite working out so we didn't get too meet up. One night though while chatting online, and having a few beers and being especially horny I sugested that he get us a hotel room. For some reason, I always imagined getting fucked there and felt comfortable. I said this half-jokingly and before I knew it, he had a room booked. I met him in the parking lot and we walked up too his room. It was pretty nice, he had some beer in the fridge and I had brought a backpack in with some supplies.

For whatever reason, I wasn't feeling too nervous and told him that I wanted to take a shower since I really wasn't expecting this too happen. He laid out my clothes for me which included a short white top ( I have no idea what it's called but it looked good), a plaid skirt with a belt and a white thong. After using the restroom and jumping in the shower I got out and it finally hit me. All of a sudden I was terribly nervous. After smoking a cigarette in the bathroom, and looking at the clothes I was about too put on he knocked and asked if everything was ok. I told him that I was just finishing up and would be out shortly. I must have been in there for a while without even realizing it. Anyways, I finally decided that yes this is what I wanted to do and too just go for it. I knew with him that if I was uncomfortable with anything that he would not push it and be ok with it.

After fiddling with the damn skirt, it took a few minutes to figure out how the hell the belt was supposed to work with it and another cigarette. I finally walked out of the bathroom. He jumped up from the bed, and had been watching tv. He came over to me and handed me a beer which I gladly accepted and took a few swigs of. At this point, I had become more comfortable and began too take on my new "feminine" role. I showed off for him by acting feminine and teasing me. He was obviously turned on and kept complimenting me on how great I looked. I turned around from him to keep teasing and before I knew it he had came up from behind me. He rubbed his dick on my ass and I gladly pressed into him as he kissed on my neck.

After some grinding on him he turned me around and we began too kiss. I'm still not sure If I enjoyed it or not, I guess it was just different kissing a man instead of a woman but I had fun. After a little while of that and him slowly going up my skirt I couldn't take it anymore and dropped down too my knees. After unbuckling his pants, I could see his hard dick through his boxer briefs. I teased him a little before I pulled down his underwear. I then began too give him head, licking and stroking him. He began moaning and before I knew it he had lifted me up and gently put me on the bed. At this point I was so turned on that I couldn't keep my hands off him and kept jacking him off as he began to undo my top and suck on my nipples. At the same time his hands were going up my skirt gently teasing my penis, which barely could stay in the small panties that he had given me. He slowly pulled off my panties and began to slowly suck me off. At this point I was in heaven and he stopped. I couldn't figure out why and didn't want it too but he got up and grabbed some lube. Before this I had done some anal play with myself but only fingers and some small objects. He continued to suck me off while he slowly entered a finger, then two.

It took a while for me to relax, but was enjoying the dual sensation of getting head and the fingers. Finally I spoke up and told him that I wanted him to fuck me. He pulled out a condom and I told him to lay down. After he put it down I tried to get on top of him but was either too nervous or too tight and he couldn't get in me. At this point I thought that it wasn't going to work at all. He was very wide but he told me too get on all fours and too try that. After more fingers and lube he finally entered me very slowly. Although it didn't hurt that much, it was definitely a strange feeling. Luckily he took it very slow and before I knew it he was all the way in. After sensing me being comfortable he began to pick up the pace, at this point I began moaning like a little bitch and buried my head in the pillows. He fucked me for a few minutes pretty hard, all I could do was moan and take it. Eventually he flipped me over and wanted me to flip my legs up. I did so but that position was way too deep for me, thankfully he was slow. After that, I had him take off the condom and began stroking him off, then had him cum on my chest which was a lot of fun. He then gave me a great blowjob and I came in his mouth.

After a shower, I thanked him with another bj and he did the same too me. I don't know if I'll ever do this again. But writing this really wants me too! I hope you guys enjoyed.
thanks for sharing your story ,i understand the nervous feeling ,i used to be like that myself until i admitted it was what i wanted ,no , needed ,i hope you are comfortable with yourself now honey,x
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Old 02-24-2013, 03:11 PM   #89
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Loved your story...sounds like FUN!!!!!
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Old 02-24-2013, 08:21 PM   #90
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I can barely remember my first experience. I was only 9 and a neighbor kinda liked me I guess : )

EDIT: Oopsies, I meant 12. I had a dacari a little while ago, hehehe : )
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Old 02-24-2013, 10:01 PM   #91
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I like a sexy pinstripe ultra short business suit. Wear black fishnet stay-up stockings with a lacy top and stiletto heels. Make sure you shave or better yet wax your legs and all your body hair for that matter. There is nothing uglier on the planet then male body hair. Do your make up with heavy eye shadow and fake lashes...long lashes and red lipstick. Tie your hair up and wear librarian glasses. Have a tight white blouse unbuttened to show cleavage. Invet in a sexy black push-up bra with some nice falsies to show under your white blouse.

Smoke a long cigarette seductivly. Cross your legs back and forth making that swish noise. Make sure he can see your stocking tops as you do this. Untie your hair and let it fal around you....and have great sex.

Rule #1 shave all remove all your ugly male body hair.
Rule#2 - The stilettos stockings and bra never come off.

Swallow each other's cum!
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Old 03-05-2013, 04:26 PM   #92
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Hot!!
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Old 03-06-2013, 08:13 AM   #93
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Great Thread

I'm enjoying reading this thread. For me, my first time crossdressing was when I was a young teen. My best friend and I dressed up in his sister's lingerie and fondled each other. It was a very positive experience and led the two of us to deepen our friendship and our crossdressing. We progressed to mutual oral and eventually, to fucking each other. We both gave each other our very first orgasms, and I can remember his cum seeping through a pair of sheer pink panties. I tasted it, found it okay, and lapped up the globs, leaving a big wet spot that made his small cock even more obvious through the panties.

We continued on for about 3 years, but eventually went our separate ways, he to a gay lifestyle and me to a straight one. I've never stopped crossdressing, though, and am currently looking forward to my first bisexual encounter since I was a teen. Unlike some others, I'm quite happy with a masculine male dressed in feminien lingerie. I love the contrast, though I'd prefer a cock and balls that are shaved so I don't have to worry about messy hairs when I give my new gurlfriend a long, warm, wet blow job.

Love to hear more on this topic.

T.
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Old 03-06-2013, 08:28 AM   #94
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Sounds like fun!

Would you like me to write you about my second time visiting a dominant man for submissive sex while dressed as a girl?

juli
juli honey i would love to read more,xo
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Old 03-06-2013, 09:38 AM   #95
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I'm enjoying reading this thread. For me, my first time crossdressing was when I was a young teen. My best friend and I dressed up in his sister's lingerie and fondled each other. It was a very positive experience and led the two of us to deepen our friendship and our crossdressing. We progressed to mutual oral and eventually, to fucking each other. We both gave each other our very first orgasms, and I can remember his cum seeping through a pair of sheer pink panties. I tasted it, found it okay, and lapped up the globs, leaving a big wet spot that made his small cock even more obvious through the panties.

We continued on for about 3 years, but eventually went our separate ways, he to a gay lifestyle and me to a straight one. I've never stopped crossdressing, though, and am currently looking forward to my first bisexual encounter since I was a teen. Unlike some others, I'm quite happy with a masculine male dressed in feminien lingerie. I love the contrast, though I'd prefer a cock and balls that are shaved so I don't have to worry about messy hairs when I give my new gurlfriend a long, warm, wet blow job.

Love to hear more on this topic.

T.
very hot
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Old 03-06-2013, 08:46 PM   #96
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Quote:
Originally Posted by Somehowyou View Post
I like a sexy pinstripe ultra short business suit. Wear black fishnet stay-up stockings with a lacy top and stiletto heels. Make sure you shave or better yet wax your legs and all your body hair for that matter. There is nothing uglier on the planet then male body hair. Do your make up with heavy eye shadow and fake lashes...long lashes and red lipstick. Tie your hair up and wear librarian glasses. Have a tight white blouse unbuttened to show cleavage. Invet in a sexy black push-up bra with some nice falsies to show under your white blouse.

Smoke a long cigarette seductivly. Cross your legs back and forth making that swish noise. Make sure he can see your stocking tops as you do this. Untie your hair and let it fal around you....and have great sex.

Rule #1 shave all remove all your ugly male body hair.
Rule#2 - The stilettos stockings and bra never come off.

Swallow each other's cum!
rule 1 and 2 are spot on I totally agree
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