Tricky Sissy

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Tricky SissyIn order for this story to make sense, you need to know two things about me: 1) I like men, women, shemales, manly men, sissy men, tall women/men, short women/men, older men/women, younger men/women. In fact, there’s not much that I’m not drawn to. Essentially, if you have warm holes, then I’m probably interested. 2) You would never know that I like sucking dick, getting fucked in the ass and swallowing cum just by looking at me and talking to me. I’m a pretty “straight” guy. However, you get that dick in me and I go to town. I don’t mean to brag, but I am very good at sucking dick. I have no gag reflex and therefore can throat any cock. I love sucking dick. I love everything about it. I love having cock in my mouth. I love the feel of the rigidity of it on my tongue and in the back of my throat. I love the feeling of cum spurting or dribbling into my mouth. I love the warmth of it and the thickness of it. I love the sounds that men make when I’m blowing them. I love the fact that I can pleasure a man tremendously with my mouth. I really get into it and that’s when the gay in me comes out, so to speak.Shortly after college, I started dating this girl, let’s call her Stacy. You need to know one thing about Stacy: she had a fat ass; it was a thing of beauty. For some reason, I never got around to telling Stacy about my sexual encounters with men and eventually, too much time had passed without me telling her, so it was my de facto secret. One night, we’re kind of drunk and we’re talking about sexual fantasies. She demurs a bit and tell me, “I’d really like to see you suck dick.” Just as one part of my brain was about to blurt out, “I’d love to have you watch me suck dick,” another part of my brain had an idea and got out, “Ehhh, I don’t know about that.” Over the next couple of weeks, we had a lot of conversations about her desire to watch me suck dick. I decided to play the role of “Guy who’s not really into it, but might be persuaded if the price is right.” After much discussion, we came up with a deal: she would get to watch me suck dick and I would get to fuck her in the ass. I’m going to be honest here: I really like fucking women in the ass. I don’t know what it is, but I like it much more than fucking men in the ass (and I really like fucking men in the ass). Actually, I know what it is: it’s the taboo. I’ve been with a couple of women who like being fucked in the ass, and it’s just not the same. I like fucking women in the ass who really don’t want to be fucked in the ass. Stacy really didn’t want to be bursa escort fucked in the ass, so naturally, I had to fuck her in the ass. This was the plan my brain came up with the drunken night when she first brought up the fantasy of watching me suck dick. I could tell her that I love sucking dick and then she could watch me suck dick for her or, I could pretend I’m not into it and hold out for a deal to fuck her in the ass in exchange, and the plan worked.A few days later, she came over my house and told me that she found somebody who would let me blow him. He was a guy from her work and he was into dudes; we’ll call this guy Jeff. We made arrangements for Jeff to come over that Friday night. There wasn’t a lot of fanfare. He came over Friday night, we all chatted and drank a few beers and then apropos of nothing, Stacy blurted out, “I really want to watch you suck his dick.” Jeff and I looked at each other, shrugged and he took off his clothes. I asked Stacy how she envisioned this going down. She said that I would be on my knees and Jeff would be standing with one hand on my shoulder and one hand on my head. This was the hard part: I had to pretend like I’d never sucked a dick before and that I wasn’t really into it. So, I sort of scooted down onto my knees and awkwardly kneed walked over to Jeff (it was only a couple of feet). His cock was long, kind of thin, but really veiny with a decently sized mushroom head. I put my hand on his dick and tentatively put it in my wide open mouth. I then closed my mouth around his cock. It felt so good in my mouth. I’d been dating Stacy for almost a year and in that time, I hadn’t sucked any dicks and now I had a lovely dick in my mouth. I started to impale my face on his long cock before I remembered that I wasn’t supposed to be good at this, so I picked an arbitrary point where my gag reflex should be and pretended to gag. A nice hearty “Hnngggh!” and made the heaving gesture. Out of the corner of my eye, I see movement and look over to see my girlfriend getting naked. I asked her, “What are you doing?” She said, “This is so fucking hot. I’m going to masturbate while I watch. Now suck his dick some more.” So I turned back, put his dick back in my mouth and did an awkward head bobbing motion for a little while. I was trying to figure out how to make Jeff cum without making it obvious that I’ve done this before when Stacy started giving me pointers. “Put your hand on his dick in front of your mouth and move your hand when you move your head.” “Put your other hand on his balls.” “Stick bursa escort bayan your tongue out a bit and lick his cock backwards.” “Don’t just move your head back and forth; nod your head a little as you go back and forth.” “Yeah, there you go. Now you’re getting it. See how deep you can go.” After a few minutes, I felt like she had given me enough pointers where I could do a half decent job without revealing my cocksucking prowess. I then had a thought: a straight guy would now be worried about the cum. So I stopped and asked Stacy, “What do you want me to do with the cum?” Much to my surprise, she said, “Swallow it, bitch!” Again, playing the part, I protested and she said, “If you’re going to fuck me in the ass, you’re going to swallow some cum.” I decided to act resigned to my fate and I got back to sucking Jeff’s dick. After a few more minutes, Jeff said, “I’m going to cum,” and Stacy said, “Don’t tell him. Just cum in his mouth.” Wow, I had no idea she had this side to her. Of course, she had no idea that I was secretly enjoying this and that my cock was rock hard and leaking tons of precum into my underwear. Thirty seconds went by and then Jeff started moaning and pumping cum into my mouth. It was a huge load and I reflexively started throating him and chugging his cum right down. I heard Stacy say, “Holy shit,” and then she started moaning as she came. I opened my eyes and looked up and Jeff was looking down at me with a look of complete and utter surprise. I said, “I have to rinse my mouth out” and walked into the bathroom. I turned on the faucet, but there was no way I was washing this beautiful taste out of my mouth. I laid down on the floor and jerked a thick load into my mouth. I kept tugging my dick as I swallowed my cum and about 20 seconds later, I came in my mouth again. I got up, turned off the faucet and walked out. Jeff had left already and Stacy said, “That was amazing. When can we do that again?” I said, “We can talk about it after I fuck your ass.”The next night, I fucked Stacy’s ass. It was wonderful; she hated it. We started with her on her back and her legs spread in the air. Her ass was thick and her asshole was lovely. I thoroughly lubed up my dick and as it slid into her ass, she took in a sharp intake of air and said, “Easy. Easy.” I took it easy for a little bit, but then I started fucking her ass. She was making all kinds of pained sounds and it took all of my concentration to keep myself from cumming. I then closed her legs and rolled her to her side and really started pounding her ass. escort bursa After a minute she said she needed to change positions. So I told her to get on all fours. I fucking reamed her asshole. I got up on my feet and really gave it to her. I don’t have the biggest cock, but I’ve been fucked in the ass by guys with comparably sized dicks and it does feel filling, for lack of a better word. She moaned, and squealed and made all kinds of sounds to indicate her discomfort; it just made my cock harder and my urge to cum greater. Finally I couldn’t hold back anymore and said, “I’m going to cum.” She said, “Not in my ass!” I replied, “If I’m going to swallow cum, you’re going to take a load of it in your ass.” Ten seconds later, I unleashed a torrent of cum up her ass. I thrusted so deeply and hard that she yelled out in pain. Her yells made me want to cum again, so I took my still rock solid dick out her ass and started jerking off until I shot another huge load on her back. She turned around and started saying, “Jesus, what’s wrong with you?” when a jet of cum hit her in the face. We both couldn’t help but laugh.The next day, she told me that she wanted to watch me suck dick again, but wanted to know if she could do something else in return. I said, “No way. Last night was great. If I’m going to suck dick, you’re getting fucked in the ass.” So that was our agreement. Just about every Friday, she brought a guy to my house and I blew him. Eventually, I didn’t have to pretend that I was bad at sucking dick and that’s when I was really able to enjoy myself, but I never let Stacy know that I was enjoying myself. I always pretended to wash my mouth out afterwards while I blasted my load into my mouth, even though most times I’d cum in my pants while sucking them off. The next night, I’d fuck the hell out of her ass. She never did get used to it, thankfully. After about 2 years, Stacy and I had a bad break up. As she was walking out of my house after yelling at each other for an hour, she turned around and said, “You suck dick like a faggot. You moan and get all gay and act like a sissy and I could see your cum in your pants. Fucking faggot.” I replied, “No shit. Do you know how many guys I fucked and sucked before I met you? Dozens. I fucking love cock. I just did all of that so I could fuck you in the ass. I loved sucking dick Friday night and fucking your ass Saturday night. Now get the fuck out.” The look on her face was great. What was even better was that I had all of those guys’ phone numbers. After Stacy and I broke up, I ran though the whole list an uncountable number of times. To be extra spiteful, I’d take pictures of me fucking these guys and text them to Stacy with a note like, “Thanks for introducing us,” or something equally dickish.

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