My sexual life (true stories)

[jtguy31]

Hey all! I'm a newbie but really excited to be here. I'm 31 and bi, and have had a pretty incredible sex life from a young age (younger than I'm allowed to post, anyway.)

Since I can't really tell the "first time" story, or a lot of what came after that, I figured I'd at least talk about some of the things I've done since turning 18.

I teach high school, and although nothing inappropriate ever comes up in class, a lot of my former students like to stay in touch after they graduate, and they add me on FB. I don't make a secret of my bisexuality on there, though it's not like I flaunt it, either, so people know who I am up-front.

About 4 years ago, one of my students added me as a friend on graduation day, and once he was no longer a student, we began a friendship online. To protect his identity, I'll call him Matt. Matt was one of those really smart students who was also incredibly shy and seemed like a bit of an outcast. It wasn't until we began chatting online that I really felt like I knew him at all. Over the course of a couple of weeks, he opened up more and more, and it seemed like we got pretty comfortable with each other. He and his girlfriend had just broken up, since she was going off to college, and there were a lot of late nights where I tried to talk him out of his funk and let him know that hey, we've all been there. Heartbreak is never easy, especially your first.

I'm not sure when I began to suspect that Matt might be interested in something more, because there wasn't a specific moment or thing that he said. But I did begin to get the instinctual feeling that he might be bi, or closeted, or just curious. You know how it is at that age. I did know, however, that his only sexual experience had been with his ex-girlfriend.

Ok, to the story:

I was online late one Friday night, because I don't have much of a social life, and up pops a chat from Matt. I could tell from his spelling that he had been drinking or something, and his inhibitions were somewhat lowered. After a few minutes of smalltalk, he just asked me point blank if I liked guys. I told him that, yes, while I tend to be mostly attracted to women, I do have some attraction to certain males. Now, mind you, at this point I'm getting a little bit excited, because he is cute!

In his tipsy way, he asks if that attraction includes him. I said that I thought he was good looking, and that if we hadn't had a teacher-student relationship, that I'd have probably talked to him. He seems relieved by that, and proceeds to tell me that he has never been with a guy before, but that he does feel the urge sometimes. I say it's natural. He asks when I knew, and how I got started, and I give him the story. I was 8, etc. We chat for a while and he finally goes to bed.

The next day, he gets online and apologizes for drunk PMing me the night before, and that he's sorry he got inappropriate. I tell him not to worry about it, that I didn't have a problem with the conversation. He seems relieved, and after talking about unrelated stuff for a half hour or so, he finally drops the bomb and asks if he can come over. Now, up to this point, I've never had a student or former student at my house, but we're both of age and there's no longer an ethical issue, so I say sure, come on over. I give him the address and he says he'll be there in 15 or 20 minutes.

As I wait for him to arrive, my heart's racing. I have a sneaky suspicion that things might get a little hot and heavy, which is exciting. But this in uncharted territory, so it's also scary. I also have about a decade of age on him. In my head, I'm trying to figure out if I'd be taking advantage, or just giving him what he wants. I decide on the latter.

I hear the car pull up, and the door slam. My doorbell rings. I answer, dressed in my usual summer attire of shorts and a t-shirt, and there's Matt, dressed similarly to me. It's awkward at first, but he comes in and has a seat on the couch. I offer a coke, and he accepts. Now of course there's all the chitchat and stuff that I'm going to skip. He's there for an hour or so before things start to get interesting.

"So," he asks, "do you ever, you know, look at porn?"

"Of course," I answer. "I think everyone does!"

"What do you like?"

"Depends on the day. What about you?" I reply.

"Same. I like this one star..." I forget her name. Anyway, Matt grabs my laptop from the coffee table and brings up one of her videos. She's cute. Girl next door type. We sit on the couch watching, and he gradually eases over a little closer to me. I've done enough to know where it's going, but I also know he's young and anxious, so I just finally say:

"Look, let's not be awkward. We're probably both turned on here, and I think I know why you came over, so let's not dance around it, ok?"

"Ok," he replies. His eyes don't meet mine, but his body language, although nervous, is clear.

I reach over with my left hand and gently brush my fingers over the crotch of his basketball shorts. I can instantly feel that he's wearing briefs and that he's hard. Of course, I am, too, a fact that's probably obvious through my own shorts. As I place my palm against his cock, he lets out a little "mmm" sound. It's very quiet, but very sexy. My hand registers the heat from him, and I'm anxious to see what he's working with. I can tell he's average size (say 5 or 5.5 inches and a little thin) but I want to see it.

Since it's my house, I decide to take the lead, so I get down from the couch and kneel between Matt's knees. He watches me, shy but interested. I give him a coy smile, and reach up to his waistband. He obediently lifts his hips and ass up, allowing me to pull his shorts and briefs off. I toss them to the side, and look greedily at what's in front of me.

Matt's throbbing prick. He's not circumsized, and his foreskin is covering about half of the head. Like most teenagers today, he is completely shaven, all the way up to his belly button. He's got naturally olive skin, and he's pretty skinny. I lean forward and take his penis in my hand.

"Nice one," I tell him quietly. He nods and gives me a little smile.

His prick has a slight upward curve to it, and I pull it downwards a little as I pull his foreskin the rest of the way down off the head. I feel his pulse, which causes his erection to throb in my hand. The head swells a bit with each beat. Since it's his first time with a male, I want him to enjoy it, so without breaking eye contact, I very slowly begin tracing my tongue over the head of his cock. I give the underside extra attention, flicking it a little with the tip of my tongue, and then back over the top. His facial expressions let me know that it feels good.

I finally take him into my mouth. I can taste the slightly salty hint of his precum, and I allow his cock to penetrate my mouth, over my tongue, all the way in. I give a couple of gentle sucks before backing off nearly all the way, until just the head is in my mouth. Then, I begin to slowly jerk him off with my right hand, all the while using my tongue on his glans. I swirl around it, fast, and use my other hand to gently rub his smooth balls. He seems to really love it.

Before long, I feel those balls begin to tighten in their sack, and Matt's penis gets even harder. The glans swells in my mouth. He's going to cum.

I pull the head out of my mouth and continue pumping him with my hand, licking from his sack up the shaft as I do so.

"C'mon, Matt," I whisper, "I want you to cum for me." He moans and I can see his body tense up.

"That's it," I tell him, "let me have it." I stick my tongue out and aim his slit into my mouth. As a jerk him, I make sure to slap the bottom of the head against the wide, flat, hot part of my tongue.

Without further warning, I feel and taste what I want. The first wad shoots straight into the back of my mouth, damn near down my throat, and I swallow it quickly before it makes me cough or gag. Matt bucks his hips upwards, and after the second spurt of his semen, I take him into my mouth again, deep. He cries out, "oh my God!" I suck pretty hard, feeling the contractions take him and tasting his cum. I hold it in my mouth, savoring it. I like the way my cum tastes, and I do enjoy other men's, but there's nothing like an 18-year-old's. Hot, so very hot, and thick.

I let him finish cumming in my mouth, swallow his load, then lick what remains off of his now-receding hard-on. I squeeze the last drop out with my hand, and lick it off with the tip of my tongue.

Matt finally relaxes.

 

[justmeincal]

Would love to hear more.

 

[Craiger]

By all means, please continue! Welcome to the story forum, JTGuy. Quite an erotic first time for Matt. I hope there will be much more to this new experience. Thanks for sharing.

Craiger

 

[Autolycus]

Welcome to the story board - new contributors are always appreciated. Good to see you have recognized the age requirements

 

[jtguy31]

Yep yep, way more to cum, lol. I've got some pretty good experiences to talk about.

 

[BiMike]

Nice one . loved it ,lets hear more

 

[jtguy31]

Continuing the Matt story before moving on to others...

I didn't hear from him for a week or two after that encounter. He'd pop in and out on FB, but we didn't chat. I think he was probably adjusting to the newness of it, figuring out his own sexuality, etc. I understood.

Then, one Sunday, I was watching the game at the house when there was a very soft knock at the door. Opening it, I found Matt, and invited him in.

"Sorry for disappearing," he said. I told him not to worry about it.

We watched the rest of the game uneventfully, without much discussion. When it was over, I offered him a beer, which he took. I mixed myself a Crown and Coke, and sat down on the couch next to him. We talked about what had happened, and he admitted that he enjoyed it, and that he thought he had come to terms with whatever it meant.

"I have to tell you," he said, "that I sort of had an attraction to you all the way through class. I never got the vibe that you were checking any of us out or anything, but I couldn't help wondering."

"That's pretty normal," I replied. "I had crushes on teachers, too."

"Did anything ever happen?" he asked me.

"No, not with a teacher or anything like that. Older boys, yeah, and later on there were...other authority figures. And believe it or not, you're the first former student I've fooled around with."

He paused for a minute.

"It's pretty hot, right?"

"Yeah," I said. "Kind of a porno situation. Student and teacher. Yeah, it's hot."

By this point he had drained his beer and asked for another, which I provided. He emptied that one pretty quickly, too.

Setting down the bottle, he looked over at me and ran his eyes up and down my body. I already had about a half staff going, and his eyes lingered on the bulge in my jeans. Without a word, he reached over and began to undo my belt. I let him, and then allowed him to unbutton my fly. My boxers had come open in front, and my shaved prick was exposed, and getting harder. He pulled it out and leaned down. I watched as his mouth opened and he lowered his face onto me. His mouth was hot and wet, and I immediately was rock hard.

I was a bit surprised by his enthusiasm, to be honest. For someone who had never given head before, he seemed to be eager for it. There wasn't a lot of delicate playing around; he just took my prick and started sucking it for all he was worth. His pace was pretty fast, and as tightly as he had me, the pleasure was too much, so I had to tell him to slow down.

"My head is really, really sensitive," I told him.

He took that in stride, and began to focus his attention more on the shaft, only hitting the head every 4th or 5th stroke, which is what I like. I leaned back and let him do it.

He was making wet, sloppy noises with his mouth, and it felt and sounded like he just couldn't get enough of my dick, which I found absolutely sexy. He was greedy for it. I allowed him to do this for several minutes before stopping him and asking him to follow me to the bedroom, where it would be more comfortable. We walked in there, me with a stiff one sticking straight out from my unbuttoned jeans, him still fully clothed.

The room was dark, but there was enough sunlight through the blinds to be able to see, once our eyes had adjusted. Before climbing into the bed, I grabbed the bottom of his t-shirt, and he lifted his arms to allow me to take it off. Then I lowered his basketball shorts, pleased to see that he wasn't wearing any underwear. His young cock sprang up to attention. While sucking me off, he'd apparently gotten a little wet himself, so I took the opportunity to nab a bit of his precum on my finger and lick it off. Then I removed my own clothes.

Climbing into bed, his head was oriented the right way, so I flipped. I guided him into position on his right side, with me on my left, and I eagerly went for his hard-on. He took mine into his mouth again, and we spent a while sucking each other off like that. When my own pleasure got almost unbearable, I'd come off of his dick and jerk him off with my hand, looking down at my crotch and watching my shaft going back and forth into his eager mouth. I spit on his dick, and used that for lubrication as I stroked him. His foreskin was retracted, but it formed a nice, thick bunch at the base of his cockhead, which was different from mine, which is cut. He aped me, and when his own mouth got tired he would pull my prick out and stroke me, too, using his own saliva.

After a bit, he looked down at me as I was sucking him and said, "Mr. Ty, I want to taste your cum."

I could certainly handle that. Taking a more dominant role, I told him to get on the floor on his knees. He adjusted quickly to being submissive, and said "yes, sir."

I half-stood/half-sat on the edge of my bed, and he obediently got down on his knees in front of me.

"Suck my cock," I told him.

"Yes, sir."

He got going again, furiously, as if he couldn't wait for me to blow.

"Masturbate." His right hand went down to his prick and he rubbed it, first with the leftover spit, and then, as that dried, he used his foreskin, rubbing it back and forth over the glans. All the while, he's taking me as deep into his mouth as he can, which is almost all the way down.

One of my quirks is that it's often difficult for me to cum when someone else is in control, so I knew I'd have to assist him. I felt the intial stage of an orgasm coming on, so I told him to stop going up and down on my prick.

"Put just the head in your mouth," I told him, "and use your other hand to jerk me off, right under the head." He did this. I could feel his tongue swirling around the head of my penis inside his mouth, and the suction.

"That's it," I cooed. "Good boy...just like that. Do you want my cum?"

"Mmm hmm."

"Okay, here it comes."

I reached down and pulled my dick from his mouth. "Spit on it," I commanded, which he did. Using his saliva, I began stroking myself, giving a lot of attention to the rim of the head. "Now, look up at me and open your mouth," I told him. He'd seen enough porn, I guess, so he did this, and even remembered to stick his tongue out. He was still masturbating, and watching him pushed me over the edge.

I slowed my strokes and positioned my head right on top of his outstretched tongue. I'm not a shooter, so the first wad oozed out and, although he was a little surprised, he only flinched a little. As I continued to stroke myself through my orgasm, I felt something hot and wet on my shin. Sure enough, when I looked down, his prick was shooting cum, too, and it was running down my legs.

By the time I was done, he had a load about the size of a half-dollar sitting right on top of his tongue.

"Hold that there," I said.

Kneeling down, I brought my face close to his, and, closing my eyes, sucked his tongue into my mouth. I could taste my own salty jizz, which I have a tendency to swallow sometimes, and under that, the taste of Matt's mouth. I rolled my cum around in my mouth as I french kissed him, then traded it back into his mouth. He swallowed some of it, and passed some back. We traded the load for a minute or two before we had gotten it all down. When it was over, I broke the kiss, gave him a wink, and told him he was welcome to use my shower.

 

[Craiger]

Now that was erotic! I think Matt needed a little libation to calm his nerves, but when he was calm....look out. I hope this isn't the last we hear of Matt. He seems to learn fast and is eager to do so. Great update, JTGuy.

Craiger

 

[workingman1291]

The only word that comes to mind is: Nice.

 

[jtguy31]

(Note: the following is true, but certain details have been changed to protect identities and comply with site policies. If you really want to know which details were changed, PM me. Also, if there's something you want to know more about, or a request that you have, please let me know. I'm more than happy to oblige.)

The friend that I've had the longest is a guy named AJ. He's 4 years older than I am, and I think I was in about the 5th grade when we started riding the school bus together. We're still friends to this day, and have had quite a few 'adventures.'

I suppose it was AJ who first clued me into the fact that I was bisexual. Both of us would probably identify as "straight," and we've both either married now or have been married to women. And really, neither of us is particularly interested in a lot of men. But there was always some level of attraction between the two of us. We'd been friends for years by the time anything sexual happened.

Without a doubt, it was me who instigated our sexual relationship. And it certainly didn't happen overnight; I'd say from the time I started really wanting something to happen until it finally did was in the span of a year or more. When you're at that age, and especially given the time period, you aren't really trying to just come out and *say* what you want, because you don't know how the other person will react, and of course you don't want to make the friendship awkward, or lose it altogether.

So the first steps I took were a little bit sly.

Since we were basically best friends, we'd stay over at each other's houses quite a bit. He actually lived behind me just a couple of streets over, so it was within walking distance. And there were lots of days where we just hung out together at one of the houses, although it was usually mine since his mom didn't work, and we could chill at my place alone.

I guess the very first thing I did to guage his reaction was this: one night when he was staying over, we'd been playing NBA Jam on the SNES for a few hours, and it got to be fairly late. I went to take a shower, and while I was in there I remembered that I had a pair of black spandex bike shorts in the bathroom. These things left absolutely nothing to the imagination. So when I got out of the shower and dried off, I slid them on, without underwear, and checked myself out in the mirror. They were so tight that you could very obviously see the outline of my cock--pretty much every detail. If you've checked out my selfies here at JUB, you've probably noticed that the crown of my dick is pretty big. A good bit bigger than the shaft, anyway. And believe me, you could see the outline of the head through these shorts. Looking at my rear, I was also happy, because although I didn't have much of an ass, these bike shorts fit really snugly and accentuated what I did have. I actually got an erection while looking in the mirror and thinking about my showing off to AJ, and had to wait a few minutes for it to go back down before I came out of the bathroom.

When I did so, he was playing the game single player, and didn't so much notice what I was wearing. I sort of strategically placed myself slightly in front of him and over to his left, and put a pillow on the floor so I could lie down. I just kind of lay there on my back, waiting. When his game was over, he turned to say something to me and stopped short. I think it flustered him a little, but he tried to cover it. As we talked, I could see him stealing glances at my crotch. I had to concentrate *really* hard on not getting a boner, since that would be just too obvious!

I remember at one point we were both sitting on the floor, indian-style, and that was when I really caught him looking. Because of the way I was sitting, my soft cock was sticking out pretty far in the shorts, and it was just begging for attention, lol. I tried to see if he was a little excited downstairs, but I wasn't able to tell.

Another time, he was working on an essay on my computer. In my bedroom at that time, my parents were storing this treadmill, and it was right behind the computer desk. So, again, I tried to be all coy and flirty. Although at that time I work briefs every day, I had a few pairs of boxers that I'd wear over my briefs when I had to change out for gym. One pair in particular was really, really loose around the legs. Like, there was 3 or 4 inches of space there. So while he was working, I changed into those, but this time with nothing under them. Then, I came up and hoisted myself into a seated position on top of the treadmill's handhold. I knew that, in this position, if he looked back he'd be able to see right up my boxers.

He would look back at me while we bullshitted, and score! He stole glances up my shorts every time he turned around, trying not to make it too obvious. That got me so excited that I started getting hard, so I had to move over to my bed and lie flat. That way, at least I could arrange my cock to lay on my belly, somewhat flat, and wouldn't make a tent out of the underwear. My position on the bed, though, still afforded him a view up the legs, so I made sure to adjust the shorts so that he could look if he wanted. And he did. He never said anything about it, or about the fact that I was rock hard, but I could tell that he was into it.

Oddly, the first time anything actually happened was at his house.

Our local video store (remember those?) had a "back room" with XXX-rated movies. I'd never been back there, but AJ had. One day when we were picking out movies to rent, I whispered to him that I'd never seen a hardcore porn movie. This was pre-internet, of course. So he offered to rent one, since his folks were on a trip out of town for the weekend, and I'd be staying over. He ended up getting a porno called "All That Jizz," lol. On the ride back to his house, I could barely contain my excitement, even though I was trying to play it cool on the outside. I was really stoked to finally see what it was all about.

I guess he must have been pretty excited, too, and maybe he knew that this would be a really good time to finally try something with me, because as soon as we got there, he popped in the tape. We sat in the matching recliners in the living room, facing the TV. The first scene, I remember, involved a kitchen, and for some reason the guy was cracking eggs and rubbing them all over the chick's tits. Still, I was enraptured. I'd only seen Playboy magazine before, so seeing a woman's pussy up close and spread was completely new to me. After the couple on screen fucked for a while, the guy pulled out and blew his load on her chest and face. I'd been jerking off for a while at this point, but I've never been a shooter, and I was amazed at how far this actor shot his cum. And how much there was!

So the next scene starts. I'm sort of shifting uncomfortably in the chair, because my dick is screaming for attention in my jeans. AJ is doing the same in his chair.

"So," he says, all casual, "have you, uh, ever thought of doing anything with a guy?" He knew I was a total, complete virgin.

"Ummm, sure, I guess," I replied.

"How do you imagine something like that would happen?" he asked.

Now you have to bear in mind that I'd been having masturbatory fantasies about just such a situation with AJ for like a year. So I knew damn well how I thought it would go down. But I played it cool.

"Idunno...I just think the other guy would have to initiate it. I don't think I could..."

"Hmmm," he said.

He stood up. My heart started beating out of my chest.

Walking over to my chair, he put his palm into the crotch of my jeans and started rubbing me.

"Like this?" he asked.

"Uh huh," I managed to reply.

He continued to rub the outside of my blue jeans with the palm of his right hand, and with his left he began to do the same to himself. Although I was very excited that it was finally happening, I was also nervous, and just kind of sat there.

"You like this?" he asked me.

"Yeah...it...feels really good."

"You wanna get on the floor?"

"K."

So he went and got a big blanket from the hall closet and spread it on the carpet in front of the couch, closer to the TV set. We both got down on it, and he resumed feeling me up over my jeans. For my part, I didn't really know what to do. I just knew that I was really enjoying it.

"Let's get more comfortable," he told me, as he unbuttoned his fly and began to pull his pants and underwear off. "Here, I'll go first."

He got them off pretty fast, and for the first time, I got to see *his* dick. It was actually quite a bit smaller than mine, even though he was older, but I didn't really give much of a shit. His balls were high and tight, and he had a thick bush of dark black pubic hair. He reached down and began to stroke himself, and told me that I could take my pants off, too, if I wanted.

I was, of course, still nervous, and although I was definitely horny, my nerves had caused my cock to go limp again. But what the hell, I figured. I'd been waiting for this to happen for a while. So I kind of timidly took off my jeans, though I left my briefs on for the time being. I remember they were blue. AJ reached over and stroked me through them, getting me fully hard again. The head of my prick started to stick out the waistband up top, and he used his fingertips to touch it. I decided, fuck it, and slid the undies off.

"Wow, dude," AJ said, "that's...really nice!"

"Thanks," I replied. "I like yours, too."

"You can touch it if you want."

Finally! Still a bit nervous, I reached out and took my friend's dick in my hand. I'll never forget that first time--he was rock hard, but the skin was soft and smooth and hot. He continued to stroke me. Although I really wanted to just stare at his penis, I didn't want to come off as completely desperate, so both of us kind of averted our eyes to the porn on the TV. We scooted around so that we were at about a 45 degree angle to each other, so that we could jerk each other off while still basically facing the TV. For me, I always masturbated by sliding my hand all the way up my shaft and over the head, so I initially did that with AJ, too.

"Be easy with the head," he told me, "or I'll cum really fast."

Now it's not that I didn't want him to cum, but this was my very first time doing anything sexual with another person. So I backed off his glans and focused on stroking his shaft more. Since he wasn't very big, that meant that I wasn't really sliding my hand on it, but more pumping the skin up and down. He produced a lot more precum than I ever have, and it ran down into my hand and made it a little bit slick. He was using his style of masturbating on me, and it sure felt good, though it didn't make me want to cum.

So we sat there watching the porn and enjoying the mutual stroke session. When he would speed up on me, I'd speed up on him. After about 5 minutes, as the actor on screen was getting ready to cum, he said "I'm close dude."

"Me too," I responded. "Here, I'll let you finish."

So we released each others cocks (aww!) and finished ourselves. I really wanted to watch AJ cum, and I figure he wanted to watch me, too, but it was still new and so we just kept our eyes on the screen. I heard his breath when he reached his climax, and that pushed me over the edge. I looked down at myself, and aimed my dick so that my wad wouldn't get on the blanket. My semen dribbled out and landed on my belly. AJ finished and said he'd go get us some towels to clean up with, and when I snuck a peek at him I could see gobs of white cum all the way up to his chest and neck. So I figured he, like the guy in the movie, was a shooter. That excited me.

He brought the towels and we got ourselves clean. He folded the blanket back up, and, sated, we sort of went on about our normal business of playing video games and shooting the shit.

Fortunately, though, this was only the beginning!

 

[Craiger]

Aw, that first experience with ones long time fantasy. Sometimes I think youth has an advantage over us adults. The excitement is really intense and firsts seem to take us all the way to heaven. Great story, jt.

Craiger

 

[jtguy31]

I've been meaning to share this since last weekend, but you know how work is...gets in the way, lol.

Had a couple of really hot experiences last Friday and Saturday.

Friday:
Both of these involve the M4M section of a popular website, which I tend to frequent. I'm all about the "casual encounters" and "NSA" sex. Have no real desire for a relationship beyond sex. So on Friday I'm trolling through the ads, and the one that really catches my eye says "Curious for 1st time" and lists the age as 22. He's in my town, so I open the ad and it basically boils down to a dude who'd just gotten dumped by his girlfriend and figured he'd try it out with a guy. He said he was a bit timid and shy, and that he wasn't sure how far he would want to go, but that he had been curious for a while. So I took a shot and sent him an email with a couple of my pics attached, and he got back with me. He said he couldn't host, so I told him I could, and gave him the address, and he said he'd be there in like an hour.

Since I tend to be a little shy myself, and I knew I'd have to take the lead on this one, I popped a Xanax to lower my own inhibitions and take the edge off the nerves. Directly, there was a knock on my door.

The guy was cute. Tall, thin, with long blonde hair and blue eyes. I could tell he was nervous, but he came right in and sat down on my couch. I shut and locked the door and was half expecting to have to make some smalltalk, but he just softly said "are we doing this in here or in the bedroom?"

"Bedroom's better," I replied.

I led him in there, and he immediately started to disrobe. Shirt, shoes, jeans, then, lastly, boxers. He had a nice body. Not cut or muscular or anything, just thin and attractive. His prick was soft, and he trimmed his pubes, so they were fairly short. He was circumsized, and flacid was about 3 inches long. His balls were tightly drawn up. I got undressed at the same time, although I was a little more excited and had a semi going. When I took off my shorts, he stared at my cock.

"I've never seen another guy's dick in person," he said.

"It's fine, dude," I told him, "look all you want. The pace is up to you."

I was a little surprised when he walked up to me and kind of pushed my shoulders down gently, so that I was half sitting on the side edge of my bed. He dropped to his knees and grabbed my cock with his right hand, which of course made me fully hard. He tugged it a couple of times, and then leaned right in and gave it a long lick, from the base to the underside of the head. Looking down, I could see that he was getting his own erection.

He looked up at me and asked if it was okay, and I nodded.

Next, he gave another long lick and this time stayed at the head, taking it into his mouth. He didn't exactly blow me right then; it was more like he was testing to see if he liked a dick in his mouth. He just kind of held it there, the head only, and lightly sucked. Although it was different, I liked it. He used his tongue around the head inside his mouth, which was also good.

He popped it out and said "yeah, I might be gay."

"Fuck labels," I told him. "I like this shit too but I still love some pussy!"

He laughed.

"Come on up here dude," I told him.

We climbed into my queen bed and he laid on his back in the middle of it, his head propped up on my pillows. His cock was now semi-hard, so I got between his legs and started rubbing it and his balls, bringing him fully up. I didn't want to rush him, so I just kind of asked if he was enjoying it as I jerked him off slowly.

"Yeah, it's good," he said.

"Do you want me to suck you?" I asked.

He nodded "uh huh."

When I put his cock in my mouth, he closed his eyes and leaned his head back. I'm a pretty good cocksucker, so I tried to give him a really good blowjob. I made sure to cup the balls, and his dick wasn't huge, but it did fill my mouth.

After a few minutes of that, he asked me if I'd mind doing a 69, and I agreed. He flipped positions, putting his head toward the foot of the bed, with my raging hard-on in his face. He wiped my precum with his hand, saying he was sorry but not ready for that yet. I said no problem.

On our sides, we blew each other. He got more enthusiastic with his sucking as time went on, and I of course gave the best head I could give. I've always been turned on by first timers. There's something naughty about it that I get off on. Anyway, as he gave me head I felt myself approaching orgasm. Since he hadn't wanted my precum in his mouth, I didn't figure he wanted a load in there, either, so I told him I was about to go. He backed off my cock and laid there for a second before he said, "how about you go on my chest? I've always wanted to know what that felt like."

"Okay," I replied.

He rolled onto his back and scooted over to the edge of the bed, and I got on my feet next to him. It didn't take but a few strokes to get me there, and I aimed my prick at his belly and chest. He masturbated as I shot my load on him. I always kind of thought it was hot, so I bent over and licked some of my jizz from him, swallowing it.

Once that was done, I told him I wanted to make him cum, and he asked me to just jerk him off rather than doing it with my mouth. I got him to scoot up to the edge of my bed and I got down on my knees and stroked him. He didn't take long...his breath got faster and I could feel his cock stiffen with the oncoming orgasm.

"Spray your cum on me," told him.

He released, and I directed his semen onto my mouth and face. He actually had a pretty good load of cum saved up, I'd say about 4 good, full spurts. It was thick and hot and salty.

I grabbed him a towel to clean up with, and he thanked me, got dressed, and left.

I have his cell number programmed, so there may eventually be a round 2!

Saturday coming soon!

 

[jtguy31]

Saturday:

Since I'd had a nice little hookup the night before, but it was kind of pure and innocent, I decided that the next day I wanted to get down and fucking dirty. So I took to the same website and placed my own ad in the casual encounters section. The title said "I want to make you cum." In the ad, I said that I'd travel to any of the nearby towns, or I could host.

I placed the ad at like 8am Saturday morning, and by 10 I had over a dozen emails from men who wanted to get together. The overwhelming majority were "straight" men in marriages or relationships who just weren't getting enough, and most of 'em wanted me to come to them. So I set up some appointments. I'd said in the ad that I didn't need recip, but that I wasn't against it, either, and that I guaranteed that I'd make you cum with my hand or my mouth. Anything else would have to be negotiated. I don't really like anal, top or bottom, but I've done both, and while I didn't want to put it on the 'net, I'm willing to do either for the right price. Can't decide if that makes me slutty or not, but fuck it.

I'd planned everything out so that I'd start closest to home and work my way outwards.

The first place I went was the house of a middle-aged man who was gay but not in a relationship and just into hook ups. He'd emailed me to say that he wanted to have me come relax with him in his hot tub naked. Maybe something would happen, maybe not.

He met me at the door in a speedo, and was attractive enough. You could tell he took care of his body, anyway. He was the most fem of the guys I met that day. We said our hellos and he brought me into his sunroom, where the spa was. We got naked and stepped into the hot water, and he sat next to me. For the first ten or fifteen minutes, we just chatted--smalltalk, and he asked if I wanted a drink, which he got out and made for me at the minibar. When he got back in and sat down, he put his hand on my inner thigh.

He said that he invites a lot of guys over to the hot tub, and mostly just does it for the eye-candy, but sometimes he gets excited. I guess I was his type. His particular thing was to watch someone masturbate while he jerked himself off. So, following his instructions, I sat up on the edge of the hot tub and stroked my cock for him. He stayed in the water and masturbated. As he got close to cumming, he shifted his position and put one of the jets of water right on his ass, and that made him cum (I, at this point, hadn't.) He shot his load right into the water, then he thanked me and said that I could finish if I wanted, or I could take off. Since I had other business to attend to, I stopped jerking, dried off, and bounced. I did enjoy watching him get off over me; it's flattering.

Next on my list was a guy who I'd seen put ads up before. He's got his own gloryhole in a shed behind his house, and likes for people to come suck his cock through it. I'd told him that I'd be down, but he'd have to wear a rubber, which I'd provide.

So I follow the directions he gave me and find his house, which is a bit secluded. Sure enough, there's the shed, and the door was unlocked. I went in and the glory hole was directly across from the doorway. I shut it behind me and went up to it. I guess he'd heard me arrive, because a limp dick appeared through the hole. No idea what the guy looked like, his age, etc. I just know that he had a thick bush of black pubic hair and his cock was a little on the small side. I don't give a shit; I just like cock.

I put my hand around it and stroked it enough to get him hard, then I applied the condom I'd brought. It's one of the thin ones that transfers heat really well. Once it was snug on him, I got down on my knees and started sucking. I've done the gloryhole thing quite a bit, and although it's pretty fucking hot, you have to be careful not to hit yourself in the nose against the wall. And since this guy wasn't well-endowed, I couldn't be as voratious with my blowjob as I usually am.

Still, I could hear him moaning on the other side of the wall, so I figured he was doing alright.

It took about 6 minutes or so to get him off. I felt his dick swell up and pulse as he shot his load into the tip of the condom. I went ahead and kept him in my mouth and kept going up and down on his cock while he came, since there was protection. Once he'd gotten off, he pulled his softening dick back through the hole, and since he'd specified that he only got blown and that was all, I left.

Guy 3 was a college student. We'd agreed that I'd give him a lubed handjob. I showed up at his parents' house (they were out of town) and he brought me into his bedroom, where he had a twin-sized bed and a bottle of baby oil. He was a little shy about the whole thing, so I just unbuttoned his jeans and slid them down, along with his boxers. I got his shirt off him and told him to lie down on the bed.

I applied a liberal amount of the oil to my hands and started rubbing it into his crotch, which was fully shaved bald. His dick sprang to attention, and I wrapped my hands tightly around it and began stroking. This guy was certainly well-endowed. Once hard, it was a good 8 inches long, and thick. He was uncut, but the head of his cock was so big that, once hard, the foreskin wouldn't come back up over it.

While I stood there and jerked him off with the baby oil, I felt his hand reach out and start rubbing my crotch through my pants. This was the first attention my dick had had all day, and I was way horny, so I appreciated that. Pretty soon, he had unbuttoned my fly and pulled my cock out, and was giving me a handjob, too. He pulled me closer to his head, and turned to the side so he could blow me. Kid was good! I had trouble concentrating on giving him his handjob. I felt myself nearing climax, so I told him "Hey...I'm going to cum soon, dude."

He looked up at me and practically begged for it. "Cum in my mouth!"

I wrapped my fist tighter around his nice big prick as he sucked me to completion. As I filled his mouth with what I imagine was a pretty fat load, he came, too, shooting huge wads of stringy cum onto his own chest and stomach. Basically, he came like only the young seem to do. I had to taste it, so I bent down and licked a bit from the bottom of his neck. It had that sweet taste to it, like he had been eating a lot of sugar, which I love, so I continued to lick up his nectar until all of it was gone. He'd swallowed my load, and before I left I made sure to save his number in my phone (and vice versa) because I definitely want to play with him again!

And now the last one, number 4.

This man lives out in the sticks, and in his email had told me he wanted lots of kissing, body contact, etc. Kind of an older guy--I think 55. He'd sent a pic of his body and cock, and it wasn't bad.

He was, by far, the kinkiest dude of the day.

He has been divorced for like a year now, and I guess decided to just embrace his inner gayness and go all out. I can't fault the guy for that. Since I'm considerably younger than him, he wanted to play out a dad/son fantasy, and I was game. Been there, done that.

He wanted to call me Todd, and me to call him dad or daddy. First thing he wants me to do is get naked and do some chores. So I take all my clothes off, and this guy gets me to his kitchen and has me washing dishes at the sink. He's very excited that I'm shaved bald downstairs. At this point, it's been about a half hour since my orgasm, so I'm certainly turned on, but not explicitly hard. My limp cock is hanging on my smooth balls, and I'm kind of impressed with the size of it--looks nice and thick.

Next is running the Hoover naked.

The man, Rick, gets in his recliner and takes his dick out to stroke it while he watches me. I make sure to face my ass to him whenever I have to bend over and pick up something the vacuum won't get.

Once that's done, he has me go back to the kitchen, with him following behind. His cock is hard and sticks out in front of him. It's average sized, cut, and he also has a bushy patch of dark pubes. He's muscular and well-tanned--probably a blue-collar worker of some type.

"Bend over the table," he tells me.

I say that I'm not there to get fucked, at least not for free, and he tells me to relax, that he just wants to rim me. So I bend over his kitchen table, with my legs as far apart as I can manage, and he gets down there. I feel his rough hands spread my ass, and he begins to eat my ass out. Like I said before, I'm not huge into the whole anal thing, but getting rimmed *does* feel good, and it got me hard again, though my dick was kind of pressed up against this fucking oak table.

If you've looked at my pics, you see that I also try to keep my asshole shaved, and he seemed to really enjoy the smoothness of it.

"Your ass tastes so good, son," he said.

"Thanks, dad," I replied, feeling just a bit dumb.

He slaps my right buttcheek, hard, leaving a red handprint.

"You like it, don't you, Todd? Having your old man lick your little hole?"

"Mmmm, yes sir," I said, "I love your tongue on me! Please give me more, daddy!"

He reattacks my asshole with his mouth, this time shoving his tongue inside as far as it can go (which, you'd be surprised, was pretty far.) After a bit, he stops and says "now, suck daddy's cock."

He sits in one of his dining room chairs, and I sit indian style on the floor while I blow him. He's way into it, telling me to jack off for him while I do it, which I of course do.

After about 5 minutes, during which time I have to swallow quite a bit of his precum, he says "Todd, what is it gonna cost daddy to get into that tight little ass?"

I pop his dick out of my mouth and, stroking it with my hand, say "Five hundred. And you gotta wear a rubber, daddy."

He's not having that.

"A rubber? Fuck that, you little cumslut. I want your ass bareback."

"Then it's gonna cost you," I say with a smile, still stroking his member.

He offers $700. I refuse. He goes up. I refuse.

Finally, at $1500, I tell him he can have me.

Now, I don't know why he wants to fuck me on his kitchen table, but he does. He gives me the cash, which I put in my billfold, then he has me bend back over the table.

He's got some kind of lube, which he uses on himself, and I feel a big glob of it hit my asscrack. He tells me to talk dirty to him. For a grand and a half...shit yeah.

"Oh, daddy," I coo, "I want to feel that big hard cock inside me."

His head starts rubbing my hole.

"Mmmm, yeah," I say, "push it into me...give me what I want."

Another slap on my ass. I try to relax my anus as he enters it. I moan, even though it does hurt.

"Oh, fuck me dad. I want you so much!"

I feel him go all the way in, and his balls slap up against my own. I tighten my asshole for him, squeezing his prick.

"That's good, Todd, squeeze it tight!"

He puts his hands on my hips and fucks me. It's pretty rough, and there's some pain, but hey...I'm making fat cash and, I can't lie, there's pleasure in it, too.

I can hear the wet smacking sounds of our bodies, and he's steadily talking dirty. "You like that shit, don't you, you little fucking whore? You've always wanted me to fuck you," etc. I go along.

He lasts for a while, and I'm not in the most comfortable position, so I start begging him to cum for me. Yeah, I know it's unsafe and whatnot, but I'm willing to take it. I reach back and spread my ass, "blow your wad, daddy, please! Cum inside me, I want it so baaaad."

He tells me to get ready, and then, an instant later, boom. I feel his semen in my ass, and his strokes go all erratic. He actually pulls out after the second or third spurt, and finishes himself on my asshole. I can feel it enter me.

About the time he's finished, he gives an abrupt "get the fuck out." I barely have time to get dressed (and didn't have time to clean up, so his cum is leaking out of me.)

In the driveway, I quickly jack myself off to orgasm before getting dressed and going home.

All in all, it was a pretty fuckin' fun day.

 

[Craiger]

Wow! That sounded like a full 8 hour shift..... Well over minimum wage...

Craiger

 

[jtguy31]

Yeah, it was a long day, but worth it! IDK...I have always gotten very hot and bothered by being "used" like that. Anonymously is good, but even when it's not, I get off on it. The cash adds to my excitement, but it isn't *really* about the money.

Also, while I enjoy writing about my life, I'm also a decent fiction writer, so if y'all have any stories you'd like to read, let me know either in the thread or via PM and I'll give it a shot.

 

[Craiger]

By all means, write something for us. Give us some romance, sex and a happy ending. Always want romance to end happily.....

Craiger