My Discreet Encounters Revealed

Monthly Archives: December 2013

Thanksgiving Eve

Naughty crossdresserHim: Hey what’s up? I’m curious.

Me: Hi. How old?

Him: 21

Me: What are you curious to try?

Him: I don’t know. I’m straight and never done anything like this and I was just wondering what you can teach me?

I get so excited when I encounter first timers. I guess I enjoy being the first person to break them in and broaden their sexual repertoire.

Me: Yes I can. I’d start you off with a bj and see how comfortable you are.

I think a bj is reasonable right? How else would I start him out—a hand job? I suppose if he was very nervous and uneasy he would have to be jerked first then sucked.

Him: Okay, what do you typical do after that?

See, he’s not too shy about getting sucked off and interested in what else we can do. He wants to do more!

Me: You can try playing with my cock. You can try getting rimmed.

Him: Hmm ok so how does this go down?

Me: You come over, follow me downstairs, drop your pants, take your cock out then lay down on the bed—then we get right down to it.

The rest of the conversation was about logistics and he was also worried about his safety. Yes, he should be safe. He is new to all this and this is his first time meeting a man in a dress off the Internet. Would I try and rob or kill him? No.

Me: You can come in and if you’re too nervous then just leave.

I never kept any of my guest’s hostage—ever. A lot of times I’ll be asked to go outside so my potential playmate can see me but I can’t do that because I can’t let my neighbors see me dressed up—ya know?

I try my best to let them know that they really are in good hands. I’m not going to harm them or try and eat them—I’ll eat their ass but nothing else. Most of time I’ll crack the door open so they can get a peek at me before they come in.

I can recall only one time someone left after coming in—I was staying in a hotel. He was a young guy, very nervous, came in, we chatted for a few seconds but then he said he couldn’t go through with it so he left. It hurts to be rejected—I know. But for whatever reason he just wasn’t feeling it or was just too nervous to do it. It’s okay.

Back to the 21yo—he continued to ask questions…whether we fuck each other and what kind of kinky stuff I was into. I was surprised that a first timer was asking about fucking—seemed like he was ready to try everything.

After work he came over. I cracked the door open so he could see me and he came in. He followed me downstairs where the lights were dim and candles were lit. He unzipped his pants and unleashed his young hard cock. I bent down and began to suck it. I was on my knees sucking it…

Me: Is it alright?

Him: Yea. Why?

Sometimes I ask how it is. Sometimes is hard for me to tell if my visitors are enjoying it. It’s more difficult with the ones that don’t make any sounds or movement at all. Just standing there while I suck them off—sometimes I just need a little assurance that I’m doing a good job. I stood up and he immediately pushed me down on the bed.

Him: I guess it’s my turn now!

He was excited to suck his first cock. I had a nice one for him that he will remember. He began to suck my cock…he really went at it. I put my hands on his head and pushed him down on my hard dick. Up and down his head went—enjoying the taste of his first cock. I sat off the edge of the bed while he stroked me. I pulled him up on the bed and removed shoes and his pants which were still around his ankles. It’s hard to enjoy yourself if you’re so constricted!

He laid back with his head against the pillow…I moved up, kneeling so my cock would be right in his face. He began to suck it more while I stroked his big thick hard dick. I massaged his balls as he massaged my cock with his mouth.

Next I got on top him…aligning my hard cock against his and then slowly grinding up and down, back and forth. Most guys enjoy the feeling. Some guys can’t handle having another cock against theirs—they get squeamish. It really does feel good though! After a few moment of grinding dicks together I went back to sucking his like a good girl. He laid back and watched I worked my mouth and up down his stiff warm cock.

Him: Do you have a condom?

Me: Yea.

Him: You want to try that?

That…meaning me fucking him. As I tell all my visitors I don’t get fucked and I rarely will fuck someone. It’s just not at the top my favorite things. For me it’s stressful putting a condom on and then trying to get in someone’s tight virgin hole. I do make exceptions every once and awhile and this was one of them. I figured I could use some more experience—so why not?

I lifted his legs high up in the air then spread them wide so I could bury my tongue deep in his ass. I wanted to see what I was getting into. I rocked his body back and forth against my tongue…all he had to do was enjoy it.

Him: Get a condom. I want to try it.

He was really eager to get fucked! I opened the dresser draw and took out a condom. Then I found the lube. Luckily I was very hard so the condom when on easily and then I lubed it up my dick. I asked him how he would like to try it and he bent over the bed with his ass off the side. I put some lube on my hand and used it to lube up his asshole. I slowly rubbed my hard cock against his hole then proceeded to enter it.

Him: Oh! No! Not into that! Ugh.

He quickly pulled his ass away.

Him: At least I tried. Sorry.

Me: It’s okay.

Well. At least he did try. He had fantasy about being fucked and now he knows that he couldn’t handle it or take it. I tried to give him what he wanted! Now both standing next to each other I took the condom off and discarded it and we began to jerk each other’s cocks. Faster and faster we jerked each other then I pushed him back on the bed with his ass hanging off the side so I could rim him some more.

After rimming him for a few moment I sat of the side of the bed so he could jerk and suck me some more. He was getting very hard and getting ready to cum.

Him: Should I just cum?

Me: Yes.

And with that he shot his load all over the side of the bed, on my sheets and got some on my face too. I gave him some tissues to wipe up and sent him off to the bathroom while I cleaned myself up. After he cleaned up and was dressed he thanked me and went on his way. This was my night before Thanksgiving that I am thankful for.