I want to hook up with a sexy, super fem shemale, not just to fuck, but to love. Wether or not im gay because of this fantasy doesnt really bother me. Problem is, im too much of a chickenshit to make that gigantic of a step into "deviance". Everyone i know would probably shun me. and i wouldnt want to lose all my friends and hurt my family over something that might not even work out.

Oh, and lets not forget that i already have a g/f thats helping me get through school and paying all the bills... but i honestly dont love her anymore...

things could be worse, but ill be fucked if this doesnt suck ass.

:(

I confess. I am a straight male with a very sexy and passionate girlfriend. I love having sexy with her, eating her out, fucking her ass (which she loves) making her scream and moan... but I also fantasize often about being a sexy lil sissy, shemale, trap cock slut for a nice fit guy (or guys). My fantasy started almost 10 years ago when I expanded my horizons and started looking at MMF porn, then that turned to bi porn and eventually I started looking at CD, sissy, trap and shemale porn. I began chatting online back when Yahoo was the place to chat. I, like so many other's, posted and pretended to be female. I started experimenting, rubing my asshole while stroking my cock, which led to a finger, then 2, etc. Over the past few years I started to wear sexy thongs and thigh highs. I have purchased several dildos for to play with. I am at the point now that I chat online on Chatave and on often get on video showing off my sexy thong and thigh highs, and get off chatting as a cock slut for horny str8, bi or gay men, sometimes women too. I will fuck my ass on cam with my favorite dildo and often will finish by throwing my legs over my head as I push my dildo deep into my cock hungry ass and cum into my wanting mouth or on my face. I love the warmth and taste of my cum. I've cum on my dildo and returned it immediately to my ass so I can get cum in my ass. I get super aroused when I suck on one of my dildo as I fuck my ass with another. I would really like to experience my fantasy. I'm not looking to be humiliated. I just want to explore my sexual boundaries.

I love jerking off in public. I masturbate in restaurants, public pools, the bus/train/plane, in crowds at concerts, at work, at school. Anywhere and everywhere I can. I also cum on and in whatever I can that will be worn, used by, eaten by or inserted into a woman's mouth. My cunt ex-girlfriends entire life would blind you under black light. My sister, even worse. Her shampoo/conditioner lasts twice as long as it should because it's at least 1/3rd my seed. Her food in the fridge always gets a healthy amount of my jizz as soon as it enters the house.

I'm trying to remember all of this the best I can. Last year I went to the store to buy shorts and socks for the summer. One of the girls folding clothes in the men's section was wearing very loose slacks that exposed the top of her ass crack and the floss that was her underwear. She had a pretty face, nice body and a perky little rack. The store was pretty dead so I decided to take my dick out under the new shorts I was carrying around in my hands and see how close I could get to her hot little ass while jerking off. As I approached she had finished folding clothes and made her way over to the changing rooms. I decided to head to the other side of the store to the women's section. I looked around and found a few pairs of assorted cotton panties. I grabbed 2 and headed back to the men's area changing rooms. There were 6 doors and a counter with all of the discarded clothes that people tried on, didn't like or want and left. She was going through the pile sorting through things. She bent over to grab a few shirts that made there way onto the floor and her slacks fell even lower. She righted herself and made no attempt to cover her tight, now half bare ass as I walked into the door nearest her. I left it open a crack so I could watch her while I finished myself. I put the pairs of panties I picked up on the little hooks on the wall so I could clean up afterwards, dropped my pants and underwear to the floor grabbed my dick, ready to go and the door swung open. The girl is standing there shocked and silent at first. I said "oh fuck". Then she quickly says "Oh my god sir, I'm so...im so sorry." Her eyes shot down to the hard cock in my hand. She said "I know you came in here but I though you were in one of the other closed doors...i...i really didn't mean to. Please don't tell my boss". I said "I won't tell if you won't" I don't know why she thought she would be in more trouble than I would be in if either of us said anything to anyone else. At this point it was a little weird that she 1. Hadn't walked away already seeing that I was standing at her job with my hard dick pointed right at her and 2. That she had just been staring at it since she went silent. Then she spoke. "Is it fun? No, I mean I'm sure it's fun but not the fun that I'm asking....i mean I shouldn't even ask" I was still in shock. It's been about 20 seconds since the door opened and now this girl is looking deep into my dick and balls while trying to have a conversation with me. "Do you mean playing with myself? Is that fun for me?" She responded "oh, um...i mean I know that's fun. I meant doing it....here." Her breathing was a little erratic. She seemed way to pretty to be acting so awkward and shy. When I first laid eyes in her I figured she was your average slut but the way she spoke screamed "I WATCH ANIME AND BOYS SCARE ME" which is just my type. This boner wasn't going anywhere. I still wasn't sure what was going on in the cute girls brain until she said "I think about it. Doing it in public I mean. Not if it's fun for other people. I......I'm sorry. I don't know if it's weird or whatever but...i don't want to leave." I figured, if she hasn't started screaming by now that she wasn't to go running away in terror at what I asked next. "Do you want to come in here with me?" My heart was racing. I've never been caught like this before and I never imagined that some sweet, attractive nerd girl would respond this way. My sister has walked in on me plenty of times and I've walked in on her. We walk around naked in front of each other all of the time so now it's just a normal thing. We catch each other a few times a month but never like this. She looked me in the eyes and said "ok, yeah". She looked out the doorway leading to the dead store, turned back and walked in with me. I closed the door behind her. "No one is going to come looking for you or call for you are they?" She said "no, they won't expect to hear from me or see me for a while". I said "ok, good. I, um...i saw you out there folding clothes. Your pants are pretty low and...i say your ass sticking out. It got me really horney. You probably think I'm some crazy pervert...which I guess I am." She said "I've actually always wanted that to happen. I do certain things, like let my pants rid too low or not wear a bra so my nipples will get hard in hopes that someone will think I'm sexy. It sounds pretty dumb now that I say it out loud to someone but to think that I got a cute guy like you so horney with just that is really hot!" I wanted to be inside this girl like mad now. I asked "Do you have like a boyfriend or anything?" She said "nooo, I don't really talk to guys. I mean, I've never been good at it or anything so I just kind of avoid guys like the plague. I'm not gay or anything, I'm just..." I put my hand on the side of her head and kissed her. I felt her lift her glasses off her face and then heard them hit the floor. As our tongues slapped each other in our mouths her hands slid down my arms over my stomach and met my still rock solid cock which was now spewing precum with every stroke. She broke away from the kiss and said "you're gonna think I'm such a spaz but I really haven't done anything like this that much" she shoved her tongue back into my mouth for a few seconds and then back out. As she tried to catch her breath she says "you know, all they guys always went for all of my friends because they thought I was some weirdo and I was always kind of a loaner and outcast.." I stopped her and said "I think you are really pretty. If you want this to happen then we are both on the same page because I don't want to stop." I kissed her hard again and then she dropped down and swallowed my cock. It only took about 15 seconds and I exploded in her mouth. She squeezed my dick once I was done to get every last drop she could get out of it. She looked up at me with those big brown eyes and gave me a huge smile. I asked her "are you ready for your turn?" Her face turned bright red and she nodded. I got down on the floor, unzipped her pants and slid them and her underwear off her little body. Her slit was perfect. She had a nicely maintained bush and I could see she had her belly button pierced at one point but didn't have any jewelry in it. I lifter her shirt. She wasn't wearing a bra and her dark little nipples were rock hard. I ran my do gets through her pubic hair, pulling her pussy lips up. Then slid my hand up to her tits, landing my middle finger on one nipple and my thumb on the other. She shivered and let out a whispered moan. Then I lifted her ass up in the air by the backs of her knees and licked her from asshole to do clit then back down. She started to pant. I stuck my tongue as deep into her cunt as I could and swirled it around. She grabbed the back of my head and pushed it in deeper. She let out a quick "oh" and I worked my way back up to her clit. I started licking it faster and faster when I pushed my middle and ring fingers inside of her. She was soaked. Just as fast as I did she tensed up and came hard. I could tell she was trying to be as quite as she could but if there was anyone else in that dressing room they would definitely know the was some chick having an orgasm a few feet away. "That...that was so amazing." She was still trying to catch her breath. "I've only ever been with one guy before...and he wasn't able to do that!" I asked "you've only been with one guy before?" She told me that when she was in high school, she had sex with a guy at a friend's house. He wasn't her type but she wanted to lose her virginity already and all of the guys at her school wanted nothing to do with her because she was an awkward mousy geek. They guy was drunk and couldn't even keep his dick hard. It sounded like a shitty first time. She said "I don't even know your name" I told her what it was and she told me her's. I already knew her's because it was on the name tag that came off as I took her tits out. She said "we can do this again if you want to. I'm not trying to be pushy or clingy or anything. Fuck, I shouldn't have said that. I swear im not clingy. I don't know why I even brought it up. I should just keep my big dumb mouth shut" I said "I happen to really like your mouth." She laughed so hard she snorted. She looked embarrassed at this so I reached over and started making out with her again. After a little while she looked at the time and said she needed to get back out where people can see her. We exchanged numbers and started making out again while we got our clothes back in. She said "I'm working again tomorrow if you had the urge to take your dick out in public again." I told her that I definitely would and not to wear any underwear.

This went on for about a week. After that we started seeing each other outside of her store. Since then we have fucked, sucked, jerked and fingered everywhere we go. We sit next to each other when we go out to eat so she can milk my cock and drizzle my cum in her food. I love this nerdy freak. I personally think our story is hot. She does too. I told her I was going to post it on here and she said that as long as I don't use our names or the name of the store we met that she was fine with it. I hope anyone that reads this is able to find the freak of their dreams in such a bizarre and super hot way too.

This is the story of my first sexual encounter with another guy.

My first time, i was in my early twenties. I never felt i was gay, and still don't now...i wasn't attracted to men in any emotional way, but physically i was curious about experimenting. I had been browsing the CL ads out of curiosity, wondering what it would be like to hook up with a guy. i knew this was not the best way to go about it, as CL was likely full of wierdo's and freaks, but i was aroused by looking at the posts and pics. Just the thought that i could anonomously hook up with someone i never met, and never have to see them again was a real turn on. i loved seeing guys post pictures of their dicks, and imagined how i'd get on my knees and suck them off. soon i was posting pics of myself. I was young, in great shape and liked to read the responses from guys, telling me my cock was hot, or that i was sexy.
Eventually i decided i would go all in and go through with it. I was working 2 hours north of where i lived, so i figured i could hook up after work with someone and there'd be zero chance i'd ever see them again. the day i decided to go for it I was checking the ads and my email all day. I was super horny and every time something grazed my cock it would leap up. by the end of the day i had found a guy that was along my way home. His dick pic really turned me on, and i kept looking down at it on my phone as i drove to his house. by this point we were txting each other for directions etc. The whole ride there i was gripping my cock through my dirty work jeans. I could feel the heat of it through my pants, maybe the horniest i've ever been.
When i finally got to his house i was relieved that it wasn't some shit hole...it was actually a really nice nieghborhood. as i walked to the door my blood was pounding in my ears and i was nervous as hell. He opened the door and said hi. His name was jim, he was slightly taller than me, maybe 6 foot...in good shape, late thirties, sandy blond hair...again, i don't find men attractive, but he was what i would consider a good looking guy. He was wearing a t shirt and sweat pants. I could see his cock bulge and was sure i was ready.
I walked in his house. It was like any other nice home (not sure what i expected). I remember two pictures by the wall, one of a slightly younger jim, and someone i assumed was his father, both wearing naval officers uniforms. don't know why but i found that kinda sexy. :-P
I then followed him up the stairs into the master bedroom, where i stood in front of him for a minute, not sure what to do. He had a warm, comforting smile as he said, "here, i'll help you with that". He reached out and cupped my thickening dick through my pants. It jumped in response and i was all in. I reached out myself and massaged his dick through the sweats. i could tell there was nothing under them, and it only made me hornier. He undid my pants and started tugging on my now throbbing prick. we worked our hands on each other for a minute or two, then i hurriedly undressed.
He layed on the bed as i got undressed. I remember seeing a glint of light off the tip of his cock as a tiny bit of old-cum formed. i got on the bed next to him and he leaned into me. we started working each others dicks and grinding, running our hands over each other. He sucked on my nipples and was kissing on my neck, but stopped there, as it seemed he could tell i wasn't down with making out, but kept kissing the sensitive spots on my body, which at this point, was everywhere. I lay there, jerking him off for a bit, but i knew i wanted to suck him off. i manuevered down to his hips and looked at his cock.
It was longer than mine, maybe 7-8". skinnier, but with a big head on it. i didn't hesitate and took it in my mouth. i was somewhat surprised at how it felt in my mouth, soft and smooth, but hard at the same time. i loved it.
....cont..
Soon he was sucking me as well. We were lying on our sides on the bed, facing opposite directions. I remember thinking he sucked dick better than the last girl i was with. I played with his balls, licking along the seam of his sack, running my tongue up the center ridge of his shaft. I loved the way his big mushroom head pulled on my lips as they slid over and back, catching on the edges. he told me he was about to cum and i picked up the pace. i was wondering what to expect when i felt his dick convulse in my mouth. I felt the first shot hit me on the roof of my mouth. I kept sucking and stroking his shaft as he unloaded his salty-sweet cum in my mouth. I wanted to swallow it, and did...probably not the best idea but i did it. I remember the tingly feeling in my mouth and comically wondered to myself if sperm were trying to burrow into my tongue.
shortly thereafter he jerked and sucked me to completion. it had been a huge build up and i shot a big load. i was happy to see that he too swallowed and felt better. As i cleaned up in the bathroom i felt mostly excited and horny, not guilty like i thought i might.
As he was walking me out we had idle conversation, as if we had not just sucked each other off. We parted ways but i did end up hooking up with him again a week or so later. He's the only guy i've ever been with twice, but the second time is a story for another day!

I once got with my ex’s best friend, who was really only interested in me because my ex told her I liked to eat ass.This is a long story, in a far away time.I was living at Job Corps at the time, I was broke and fresh out of college and needed a place to stay. I entered college my junior year of high school, so I was still pretty young for a college graduate.

The ex would never let me do anal, sometimes she would let me finger it a little, but she loved having her ass eaten. After we broke up, her friend would sometimes tease me between class. Me and the ex weren’t super serious or anything, so we all pretty much stayed friends after we broke up, but by then the ex was already with another dude, so I didn’t really hang out with her much.

One day, Friend was like, “I hear you like to lick ass” and laughed, and I said, “Yeah, I do”. She was taken aback, like she expected me to deny it, I guess.
”Don’t you know that’s gay!?” she said, and I said “No, I don’t know that”, and continued on my way.

Later on she came up to me in the cafe and said, “Are you going off-res tonight?”, it was a Friday, and we were allowed to leave for weekends if you lived in the dorms. I hadn’t been planning to, but I asked, “Why?”, and she said, “You should go off-res and take me with you”.She didn’t have to ask twice, I was now planning on it. I wasn’t sure what she wanted, but I definitely had my hopes up!

Being broke at the time, most of my stuff was still with my parents, but they weren’t going to be home that weekend, which is partially why I wasn’t going home, I had no ride and I usually hated taking the bus.

But I now had a reason, and decided I’d be taking her home that weekend. I half expected her to be bluffing or messing with me, but nope, she showed up to the bus and got on with me.We didn’t talk much on the ride home, really, and I was still half-expecting a prank or for her to want something from me.

We then had to take a city bus to my house after the first bus dropped us off, and I expected her to balk or mock me, turn around and leave or something, but she just got on with me. I was at least decent enough to pay the fare for both of us, hey, two bucks, it was the least I could do. We chatted a little about nothing in particular this time, but my mind was racing a mile a minute. What did she want? Just to get off campus for a bit? Everyone knew I always had weed, maybe she just wanted to smoke?

We got home and I met a snag in my plan, because for some reason my younger sister was still there. She was supposed to have been gone, too, staying at her friend’s to go to some concert the next day or whatever.

Once she saw that I was there, and with somebody, she made it a point to be a huge pain. “What’s going on!? Why are you home!? Who is this!?”, wouldn’t leave us alone, kept asking annoying questions, kept hovering.

Friend and I were hanging out in my room and I could hear my sister hanging around outside my door, constantly walking back and forth for no reason, nosing around, it was infuriating, what would she think was going on, and why would she want to know if anything was, anyway. We were usually cool, too, so it was really bothering me that she was behaving this way.

My sister was supposed to leave that night, but she wound up staying the entire night, I’m pretty sure it was just to be annoying, just to fuck with me. I wound up staying on my couch and let Friend sleep in my bed just so my sister wouldn’t hassle us all night, not like she should have cared, it was really out of character for her, and again, infuriating. I kind of never forgave her for it, just for how uncalled for it all was. To this very day I harbor some small resentment over it, really. Gotta be honest.

I woke up the next day and took the world’s quickest shower because I was worried my sister would drive Friend crazy and I walk out to find she left or something. Eventually my sister did leave, but she dragged it on for as long as possible, just to mess with me, and again, for no reason, we were all adults, it was really odd. I was positive that Friend would be totally bothered and disgusted with me, too. If not just for my sister’s obnoxious behavior.

Once my sister left, Friend hopped in the shower and I sat on my couch seething with rage, expecting Friend to be planning her exit.

Friend came out of the bathroom in just a towel, and walked over to me.“I’ve never had my ass licked before”, she said. Well, that was unexpected. I stood up and started lowering her towel, and she let me.

Worried my sister might suddenly burst back into the house or something, I took Friend into my room, locked the door, and got her up on my bed on all fours. She had a small butt, but it was pert, and perky. Really nice, and looked especially good bent over. Perfectly pretty little butthole, too, very tight and pink.

I spread her cheeks and started eating her ass, making my way to her pussy as well, but focusing on her ass. Hey, it was why she was here!

After a while, I was good and worked up and quite ready to fuck her. I didn’t have any condoms so I had to rely on the honor system, “I’m clean, are you clean… !?”, I asked. She said yes and I was too horny to second guess her, almost as soon as she answered, I was inside her. Warm and tight, shaved, she had a nice innie pussy.

After a while she asked if I had any lube. Fortunately, I had an old bottle in my top drawer. “Yeah, I do”.
“You can fuck me in the ass”, she whispered.
Her gorgeous ass was incredibly tight and I kept having to stop so I wouldn’t cum, I was very turned on by how quickly things had escalated.
As I pulled out and stopped, clenching my gut tightly so I didn’t bust, she turned around and started stroking me. “Wait, wait, stop” I stammered, not wanting to shoot just yet.
I laid her down on her back and fucked her ass missionary for a while, I wanted to suck her big tits while I fucked her. When I was kissing her she would lightly bite and suck my lips and tongue, it turned me on even more.
Eventually I was really close and pulled out saying, “I’m really close”.
She had these big, pouty lips and she just sat up, opened them and nodded, not saying anything but moaning in agreement.
”I’m going to cum in your mouth” I said, stroking myself to climax, “I’m going to come in your mouth”.
She puckered her sexy lips waiting for my throbbing member, I kept stroking it while resting the head on her soft bottom lip, she started pursing her lips, sucking and flicking her tongue around my cock saying, “Cum in my mouth, cum in my mouth”, and I couldn’t hold back any longer, pulling back a little and repeatedly shooting thick streams all over her pretty lips and face and into her gorgeous mouth, pushing my cock between her eager lips once I was drained, my post-orgasm shaft spasming inside her mouth. She kept sucking after I came and my whole body shook with pleasure and pain.

We fell back onto the bed and just kind of laid there holding each other and breathing heavily for a while before I eventually got up to get her a towel. While wiping herself off she said, “I’ve never had my ass licked before, all my boyfriends always said it was gross or gay… “. I was going to ask if she liked it, but that felt kinda corny, so I just left it at that. This was before ass eating was a huge mainstream thing, she kept calling it “licked”, instead of eaten, but I thought that was pretty sexy.

We took a shower together, I groped and played with her luscious, wet body, soaping up her tits and ass, rubbing her up and down. Somehow she looked even better, wet, I don’t know why that’s always the case, maybe it’s just a me thing.

Afterward, we hung around watching TV for the rest of the night. We made out and groped a little, at one point she put her hand down my pants and kept fondling my nuts, but we didn’t fuck again.
Later on out of nowhere she said, “My ex was huge. Like, really big. He liked anal and it hurt. It didn’t hurt as much, with you”.
Gee, thanks, I thought, but didn’t say anything.
We chatted randomly and cuddled, before she eventually fell asleep on top of me, later on I conked out, myself.

We had a normal Sunday morning and left for the bus stop that afternoon, luckily my sister didn’t come back home at any point. At that time I would have been happy to never have seen her again, I was still so angry.
We pretty much rode both buses in silence, got back to the center and went our separate ways. I wasn’t sure if she would tell anyone and suddenly everyone would be talking or gossiping or whatever, but as far as I ever found out, she only told my ex, who Friend claimed didn’t care, and who I don’t think cared to tell anyone else, really.

But a few weeks, maybe a month later, my Ex walked up to me in the hallway and said, “Just so you know, I only ever came when I was on top”, out of nowhere, for no reason. I’m not sure if it was out of some kind of spite or revenge for finding out, or if she just felt the need to throw that at me in the moment, but all I could think to say was, “At least you came at all!”, before walking off. It didn’t bother me much, especially since during our TV talk, one of the things Friend had told me was, “I was curious, since ‘Ex’ told me you were good in bed, and that liked to lick her ass”. Hey, thanks for the good word, Ex!

Me and Friend were still cordial, but we didn’t really hang out again after that, and we (unfortunately) never hooked up again, I’m not sure if it was because of the Ex, or if she had just, gotten me out of her system, or what. All the flirting had pretty much stopped, too, and I tried to convince myself it was just a thing that happened, she got what she wanted and was done with me, guys do it all the time for instance, but I can’t deny it was a bit of blow to my ego. The little flirting thing we had was a lot of fun, I was a little sad to see it end. And I couldn’t help but thinking that perhaps she had found my sexual abilities substandard. Not like I’ve had many complaints or anything, but hey, you can’t please everybody!
Her and my ex found a new group of weirdos to hang out with, and they weren’t too fond of me and my friends, so we all kind of drifted apart, entirely. I saw Friend in passing at a rave and didn’t know it would be the last time until it turned out it was. I saw the ex one more time, the day I was leaving the program, and she ran up to me and gave me a huge hug and said a very heartfelt goodbye out of nowhere, I hugged her back and we chatted for a bit, I eventually left, and that was the last time I ever saw her.

So I meet this girl through some friends and she’s pretty hot and she seems like she’s into me. But she also has a huskier voice and I’m wondering if she’s trans. But I have a couple of drinks and it’s been 20 months since I got divorced and I haven’t had sex in a long, long time. And she’s looking good. So, we end up hooking up but she seems nervous and I ask her what’s wrong and she asks if I know she’s not a “real girl.” I say yes, and because I’m so horny, I really don’t care and I figure I can get a blowjob or handjob out of it because I really don’t want to deal with her dick.

We fool around and she gives me the best blowjob I’ve ever had. She kept her panties on so I just focus on her giving me head and forget about what’s between her legs. It was awesome and I think that’s that. We exchange numbers but I figure I won’t call her because of the whole trans thing. A couple of days later she texts me. And I’ve had a couple of days to fantasize about her blowing me and I’ve tugged a few out thinking how awesome it would be to do that again. So in a weak moment I decide to meet her for a drink. She looks good. Super good.

We end up in bed later and I get her shirt and bra off and I’m sucking her natural little titties and I can feel her dick getting hard. She rolls me on my back and takes her panties off and there’s her semi-hard dick, but I think she could tell it made me uncomfortable. She proceeds to give me another amazing blowjob and I blow my load. We snuggle and spoon after which makes me a little uncomfortable since I still haven’t touched her dick. A little later my dick starts getting hard because it’s pressed up against her tight little ass. She giggles and wiggles against me when she feels me getting hard and asks if I want something. I’m tempted to push for some ass, but instead rub her tits and kiss her and then get her to blow me again and this time she takes my load and kisses me back with her mouthful of cum. I’m a little flipped out but kind of turned on. We go to sleep.

Next morning, I wake up with my dick hard and try to figure out if I want to try something else with her. But she doesn’t seem like she’s into it so we fool and around and she tugs my dick a little but doesn’t make me cum. I fondle her dick a little and then go back to kissing and sucking her tits because I’m a little shy about it and I think she can tell. She then lies there and starts to jerk herself off in front of me. I’m mesmerized and after she comes on her stomach, I want to go down and lick it up and then kiss her with her own cum, but I’m also flipped out because her semi-hard dick I lying there. I decide to go down and lick the length of her dick, but don’t put it in my mouth, and lick up some of the cum and kiss her. I’m slightly revolted at licking her cock and also super turned on. She seems a little relieved but splits a little bit after without saying much.

I don’t hear from her for about four days and I decide to text her telling her I’d like to see her. She asks if it’s a real date and I say yes, so I take her to dinner and she’s talkative and really fun to be with and it’s like the first time I met her. We hold hands when we’re walking and she seems super into it. We go back to her place and I start to kiss her the minute we get through the door and she pauses me and says we need to talk, but I’m thinking no, I really need you to suck my dick because she looks so hot.

She tells me she really likes me but she’s afraid I’m embarrassed and uncomfortable about her being trans. I admit I am a little shy about it because I don’t think of myself as gay and think in more traditional gender roles but tell her I really like her and think she’s fun and sexy. She tells me she likes sex with me but we need to make sure the pleasure is mutual. I say OK but am a bit afraid of what that means, and start to kiss her again and she kisses me back. She takes me to the bedroom and tells me wait there and she goes to the bathroom. She comes back in superhot lingerie and stockings and my dick starts throbbing looking at her sexy, skinny body. Her little tits look awesome and I can see the faint bulge in her panties. We get into bed and it’s superhot and I’m so turned on by her. I finally pull her panties down and her cock pops out. I stroke it some and then put it in my mouth and bob up and down. She’s moaning and telling me how good it feels. I can only do I for like a minute before I’m overwhelmed that I’m sucking a cock like I’m gay. But it’s also superhot because she’s so sexy. I start sucking her cock again and I really start to get into it and she starts telling me how good it is and how she likes it. She pulls me up before she comes and we kiss more and then she sucks me some. I’m on my knees on the bed and she’s down below me sucking my dick and I’m watching her sexy body. I have to stop her because I’m so close to coming. She lies on her back and spreads her legs. She’s only got on a garter belt and stockings and it’s all I can do to keep myself from coming because she’s so fucking hot. She asks if I’ll fuck her and I mumble yes. She gets lube and a condom and puts the condom on me. I put her legs up over my shoulders and push my dick against her ass. It doesn’t give so I push more and then I feel her sphincter open and my dicks slides into her ass. I start fucking her and am mesmerized by her cock as it jerks each time I push my dick in her. We fuck for a few minutes and I roll her over so I can do her doggy style. It’s so hot and I alternate between grabbing her tits and her dick. She says she wants to cum and wants to be on her back again, so we switch back. She wraps her legs around me as I push down on her body so her cock rubs against my stomach as we fuck. We build up and I can feel her dick twitching like she’s close to coming. I wonder if I should pull out so I can go down and suck her dick when she comes but it feels so good in her ass that I decide to stay where I am. Then I feel the cum shooting out as she starts to moan. I cum in her ass and collapse. I roll off her and lie there realizing I just sucked a dick and fucked a tranny in the ass. She’s so hot but I also feel some revulsion about it because I realize I just fucked someone who was born as a man. She seems to sense it and tells me how much she likes me and how much she likes sex with me. The endorphins kick in and I fall asleep thinking about her sexy body.

Things progress and I start to feel more at ease having sex with her. We start spending 3-5 nights a week with each other and she’s always on my mind. I get more comfortable fondling her dick and giving her head and eventually get to the point of letting her come in my mouth. I still get feeling of guilt but I push them back into the corner because honestly the sex is so good and I really enjoy hanging out with her. She’s low maintenance, fun, likes sex (and even initiates it).

A couple of weeks later we go to the beach for a long weekend. The weather isn’t great but we still walk along the beach and then fuck like mad back at the condo. At night we light the fireplace and have sex for hours in front of the fire. I’m happy like I’ve never been. I get relaxed walking in public with her. I start to get comfortable sucking her dick and swallowing her cum. Sometimes when I’m alone I start thinking that I’ve become comfortable sucking cocks and that I must be gay, but then I make the realization that I don’t like sucking cock – I like sucking her cock. I realize that I’m fine with sucking her dick because I love her as a person. Maybe I’m justifying it. I’m not sure, but now I look forward to pleasuring her and I don’t feel guilty. I have a superhot, sexy girlfriend who loves me and we have amazing sex. She was born a man. So what. I don’t care. I love who she is, and how she makes me feel. And I’m fine sucking her cock so she knows how much I love her. At this point, I can’t believe I was once so shy about touching or sucking her cock.

People on here will likely post that I’m a faggot. Which is fine. Several months ago, I might have agreed. But I’m so happy with her that I really don’t care what those people think. It’s the most satisfying relationship, sexually and emotionally, that I’ve ever been in. I come home to the sexiest woman every day, so who cares what a bunch of homophobes think.

So i've never told anyone this story. A bit of background before I start. I've trolled motherless for years now and being from a decently large city so the "underground" sex scene as like to call it was pretty decent. Most any fetisb or fantasy could be had if you looked in the right place or paid the right amount. I'm not a depraved soul but I do have some kinks I like satisfied. I'm happily married now to a normal girl who knows some of my life prior but I've never told her this story. This story takes place about 7 years ago. I was 20 and she was 18 but we had been dating for awhile. Well call her Abby. Over the course of us dating we gradually moved into some other things. We used to smoke weed all the time and her dad let us drink. He had no problem with us having sex as long as I wore a condom. She was incredibly sexy looking. She weighed 120 but she had a nice ass 36dd breasts and a pussy to die for. Was an Innie with a slight but protruding. She has amazing sexy legs and looked good in a tight dress and heels. She had these amazing lips that felt amazing wrapped around my cock. We started off pretty vanilla but after 6 months or so we started doing some off key stuff. We moved into bondage and she enjoyed submitting g. I bought her all kinds of toys and when I couldn't come over we would Skype And she would play with herself for me. Her favorite toy was a thick 10 inches and she would ride it wearing these sexy red heels. If you didn't realize I love a girl who wears heels. Close toed high heeled are my fav. Over time we would get more and more adventurous. We would drive somewhere and smoke and we'd fuck. The epitome of this was at Walmart we were fucking after getting super high and when we finished we looked up and saw we had an audience. She noticed and we left but when we got back to her place we fucked so good. We started to move into other things. We'd bang out in public out of the car on the car. We eventually started fucking on omegle. We started to do dares and we'd get more daring. It started off nice. Like I needed to wack off in the mall parking lot or shed have to flash a trucker. I started to make it crazier and crazier. The craziest was when undated her to let me tie her down and leave the hotel door open. She was reluctant but agreed after I pestered her. I sat in the closet and waited. Some people walked by and some guys actually walked into the room but never did anything. To keep her from being mad I never told her about anyone seeing. One day the guy who supplied us weed dropped off the map so we had to get a new supplier. Her parents were out of town so we had the house to ourself. We got drunk and smoked the weed and didn't realize til later it was laced. I don't know what it was but it caused her to change. She gave me the best head I've ever gotten. For some reason something changed in her and next thing I realize she's on the floor with her dog and blowing him. I'd never been into zoo before but this made me so fucking hard I had to fuck her. Ya. I don't know what happened. But the first time she was spitroasted was with a dog. I never mentioned it and she didn't seem to remember it so we moved on. We kept the course and one night a month later she went out while I was working. She smoked some of the laced weed and I felt super horny j wanted to watch her on Skype fuck herself. I don't know why I said it but it went something like this."baby if a guy hits in you I dare you to bring him home And fuck him on Skype. She called me on Skype 2 minutes later pretending she didn't get the text. She kept getting dressed and omg. I was fucking rock hard. She was wearing the tightest black dress I'd ever seen in my life. It ended maybe 3 inches from her pussy and she looked fucking amazing. When she was ready she looked st the cam and said "baby I'm headed out now. Don't hang up and she gave me the sexiest wink ever. I kept Skype up and I heard a door about 3 hrs later. To this day I don't knowbshy but my dick propped right up. I had never been so hard in my life. In see her and him walk into the room and she's with an Hispanic dude. My blood is all in my dick and my mouth is super dry as I watch them strip and his dick popped out. I swear to god his dick looked just like the dildo she loved. I'm not anywhere close to gay but jesus fuckj g Christ that dick was beautiful. She proceeds to blow him and hops on top of him facing the cam. Her pussy was stretched so good and she was moaning non stop. She looked at the cam and winked at me. She hopped off and bent over the and he fucked her from behind before blowing his load down her throat. They lay there before he left a little while later. She was panting as she walked up to the cam and asked if I enjoyed it. I had literally no words. I pretty much came my pants when she swallowed his load. She smoked a bit more as we chatted like nothing happened. Her dog made another appearance and she looked st me and said "watch this" since this content is no longer allowed on ML but she did something I had always wanted to watch. The next day she texted me and thanked me for a great night. She had no idea what she did. Little did I know our life would get even more depraved. Let me know if you guys went to hear more. It feels good to get it off my chest after all these years. Not even my wife knows this. You can believe this story or not but I guarantee you all this is 100% true. I might have left some things out because of my drug addled brain at the time and the fact I'm on an phone. Thanks for reading this guys and gals.

So, after much discussion about it in the chats, I decided that I would do a weekly column of (what I think are) interesting subjects that guys should get a little education on. Every week I'll be posting a new, somewhat lengthy post about a different topic. Feel free to comment on them, share them or just write them off.

Without further Adieu:

Gentleman : Things Your Gay Pal Would Like You to Know (But Never Says)
A Weekly Editorial Column aimed at guys from gays (well, one gay.. me)

Week #1 - Male Webcamming

Guys love watching girls cam as a rule. They're sexy, funny, show tits and even more and they are perhaps their most free and in control when infront of a cam of adoring fans. Unfortunately, male webcamming is often one of the least erotic, least enjoyable things a lady can watch. The following are some tips with explanations that may improve the viewership and quality of your cam sessions:

1) Be Like a Model : Gimme Face
Despite what men think, staring at a cam feed focused straight on your junk? Not super hot. Many people, especially women, have a basic emotional connection to sex. Your face is one of the direct connections to what you're feeling and that's hot. Summary : Your face helps sell sex appeal. Maybe let it co-star in some of your shows.

2) Say My Name, Bitch
Have you ever noticed you have to really -look- at a picture before it registers as arousing, but the sound of someone moaning can send shivers right up your back? Many sex therapists believe this is because sight actually has a very weak connection to your feelings, whereas sound has a direct line right to your naught place. Turn on the mike, even if all they hear is breathing, panting and grunts. The sounds really make it a blockbuster performance.

3) Hi, My Name is Bob. Want to Get Busy?
Wanna be a porn rockstar? Surprisingly, the road to being a sex idol (at least online) is very similar to being the life of the party in real life; get to know people. Talking with girls (and guys) without drowning them in lust or fawning over their every statement is a great way to form a connection... and once a connection is in place it's very easy to be turned on by someone.

4) I've Got a Little Something I'd Like to Share...
So, you've done all the rest but there's still a certain someone online you'd like to share a 'private moment' with? Ask them. WARNING: Asking is not the same thing as demanding, examples will follow. A properly delivered request should be courteous, maybe a little flattering, offer an OPTION to watch you if they want, and if you receive a �No� (even if you don't like their tone) you should be nothing but polite.
Example of a demand (BAD BAD BAD)
Hey Suzy, I'm jacking off right now. Turn on my cam.

Example of a request (Niiiiice)
Hey Suzy, what you're doing on cam is driving me wild. If you want, I've turned my cam on and I'd love for you to see me stroke it as I think of you.

These aren't big things, but believe me they will turn your 70's basement porn into something that people relish getting the chance to watch and maybe even talk about after the fact. This is Yesm, telling you the things your gay pal would like for you to know (but never tells you).

I confess. I am a straight male with a very sexy and passionate girlfriend. I love having sexy with her, eating her out, fucking her ass (which she loves) making her scream and moan... but I also fantasize often about being a sexy lil sissy, shemale, trap cock slut for a nice fit guy (or guys). My fantasy started almost 10 years ago when I expanded my horizons and started looking at MMF porn, then that turned to bi porn and eventually I started looking at CD, sissy, trap and shemale porn. I began chatting online back when Yahoo was the place to chat. I, like so many other's, posted and pretended to be female. I started experimenting, rubing my asshole while stroking my cock, which led to a finger, then 2, etc. Over the past few years I started to wear sexy thongs and thigh highs. I have purchased several dildos for to play with. I am at the point now that I chat online on Chatave and on often get on video showing off my sexy thong and thigh highs, and get off chatting as a cock slut for horny str8, bi or gay men, sometimes women too. I will fuck my ass on cam with my favorite dildo and often will finish by throwing my legs over my head as I push my dildo deep into my cock hungry ass and cum into my wanting mouth or on my face. I love the warmth and taste of my cum. I've cum on my dildo and returned it immediately to my ass so I can get cum in my ass. I get super aroused when I suck on one of my dildo as I fuck my ass with another. I would really like to experience my fantasy. I'm not looking to be humiliated. I just want to explore my sexual boundaries.