Had my [M] first jerk off buddy [M] today, things escalated quickly

TL;DR: found a jerk off buddy after a year of looking at this stuff, but the jo bud part lasted 10 minutes before it goes into make out, kissing, bj and 69. Did satisfied both my jo bud and bi-curious side in an hour, feel good now!

First off, its been almost a year that i stumbled onto r/jobuds subreddit and since then I was hooked to the stories and the community. I had a few jerk off sessions on kik in and off during the year.

I lurked on craigslist last week because I wanted to “get done with it once and for all” and actually do a real jo session with another. Found a guy that was about my age and shape, but the wording of the post sounded that he was more gay than straight bi-curious. I didnt mind because im a bit bi-curious so i wouldn’t have minded if during the jo session we would stroke each other.

The Turning [NSFW] [M/F] [Oral]

I was enjoying a quiet sit down in the park that Thursday afternoon, coffee in hand and the sun on my face. A perfectly, warm autumn day. I took a sip of coffee.

“Ah-BOO!” my interloper yelled from behind me.

I almost dropped my takeaway cup on my lap, dislodging the lid in the process. Coffee dripped through my fingers and sprinkled over my shirt.

“Hello Kelly. You’re late”, I said, ignoring the provocation. It would never do to appear rattled with this one. She would enjoy it too much.

The girl sat down on the grass next to me and took a cup of takeaway coffee from the disposable cardboard tray next to me.
Please meet Kelly: a jolly elf of a lass, 27 years old and quite stunning. My only complaint, if I should be forced to own one, is that her hair was cropped too short for my liking. She wore a Ramones t-shirt, blue jeans and sneakers. Or, as I tended to think of it as – Kelly’s all round year uniform.

“Hardly late”, she replied. “Blame the bus, Mr Anal”.

Achieve[m]ent Unlocked: I Sucked on a Penis

Since I was about 16, I had thought about giving oral sex to a man. At this point, I hadn’t even given oral sex to a woman, much less received it from anyone, but I had a desire to try it some day in the future. When my parents kissed me goodbye outside my dorm, the future was here.

Sucking a cock wasn’t the only thing I wanted. I had assembled somewhat of a sexual bucket list that I planned to attack in college. It mostly consisted of pretty standard fantasies: have a threesome, give a facial, have anal sex, have sex in public, etc. At this point, I was very inexperienced, so there were a lot of firsts to be had.

As soon as my parents drove away, I headed straight back to my dorm and got on my computer. This was about 8 years ago, long before I had heard about reddit, so my go to medium was Craigslist. I had browsed the personals in the areas around my home town before, but never had a chance to actually meet with anyone. I couldn’t exactly bring a stranger over to my parents’ house for some anonymous sex, and I don’t think my dad would have let me use his car to drive to a casual encounter.

today’s adventure.

As some of you know from previous posts, I am a 32 Female that is extremely submissive and has had a great time fulfilling all of my fantasies as well as those of my SO’s. I love to be used, humiliated, punished and teased at the direction of my SO, and today I am going to do it again. As some might know, a few days ago I went to a coffee shop and masturbated for an older gentleman, and due to the circumstances allowed him to finger me until I came. Well, my SO was not happy that I did something that he did not approve of in advance, and today I am going to be punished for that transgression. So part of this is to tell you what is in store for me as I get myself all worked up in anticipation.

Around 5 tonight I will be leaving the house by myself. I will have prepared myself as told, shaving myself, putting on garters and thigh high stockings and wearing a long sundress with no panties. During the day I will be slowly fucking myself with a series of dildos in my ass, until I can get the butt plug in and will leave it there until I leave.

My girlfriend, that girl from class, and their friend, or, how I lost my virginity (m/f)

I had my first “real” girlfriend, who I will call Rachel, when I was 17. We’d been seeing each other for a bit, and I’d had a couple really intense make-out sessions with her, including one that wound up with her on top of me in the driver’s seat of my car, dry humping the shit out of me in her parent’s driveway.
One night, we’re out for a drive and she asks if I want to stop by her friend Monica’s (nod) house. I knew Monica from the biology class we took together, and I liked her because she was weird and unashamed, so I had no issues agreeing to saying hi. We were at Monica’s house for about five minutes when Rachel asked Monica what her friend Pete was up to. Apparently Pete had a long-standing crush on Monica, and she had zero interest in Pete. She said he called about hanging out earlier, then admitted she wanted to get out of the house, “even if it means hanging out with Pete.” So I drove the three of us over to Pete’s house.
Pete had exclusive rights to the entire downstairs of a split-level house, complete with a padlock on the door. It was a little strange to be locked in a basement (albeit finished) with and by somebody I’d just meant, but I just wanted to go where Rachel went, so I shuffled in without a word. We sat for a while and shot the shit, and I immediately understood Monica’s reluctance with Pete. He was a little off, kind of short and the embodiment of a napoleon complex. He also had really good taste in music, so I could focus on that and ignore everything else. We were in the middle of a pretty intense game of “Have you heard of…” when I felt a hand on my leg. Rachel was looking at me intensely when I turned to face her, and she leaned over and kissed me. We went directly into passionate, sloppy teenage make-out right away. After a bit, I realized that this was the first time we made out where we weren’t in my car, so I got a little bit more bold, grabbing one, then both boobs. Rachel had zero issue with me playing with her tits, so I tried to take her shirt off, and she threw her arms up to make it easier to get off. I fumbled briefly with her bra before undoing the clasp and freeing her perky b-cups. I buried my face in her chest, licked and nibbled on her nipples and went back to making out. I dry humped the shit out of her for a change, and she reached down and played with my cock, which was already hard as fucking granite. I had her pants open and around her ankles, then off in about two seconds. She wasn’t wearing anything underneath, so I went right for her clit with my fingers, then I figured fuck it, and went down on her. I can’t be sure, but I think I was down there for about five minutes, then she pulled me up and we made out more and she cleaned herself off me.
Then the strangest thing happened. She got off the bed, and I noticed Monica had left the couch where she and Pete were doing their thing and the two girls started making out. I wasn’t sure what to do. Did they want the guys to make out? Did he want to make out with me? Is there some kind of signal, or am I just supposed to know? What the fuck is happening? Then the girls split up and Monica came to me, and Rachel went to Pete. Monica wasn’t much in the face, but man, she had an amazing body. She pushed me back to lay down on the bed and told me she was going to suck my cock, then added, “Is that okay?” I nodded furiously in the affirmative, and she took all of me in her mouth, down to the hilt. She gave an incredible blowjob, and of course, I didn’t last very long. I told her I was going to come, and she said, “Well, come then!” And my hips bucked as I exploded into her mouth. I looked over at the couch briefly and Rachel was giving Pete one hell of a handy. I expected Rachel to stop, but she didn’t. She told me she wanted to get me hard again, because she was going to fuck me. That was all I needed to hear, I guess, because I was hard again almost immediately. She told me she had to be on top, and that she hoped that was okay. Again, I nodded yes as if my life depended on it, and she climbed aboard. She was a treat to watch as she got both of us off riding and writhing and grinding and bouncing. Again, I looked over to the couch and Pete was railing into Rachel, just pounding her. Maybe it should have bothered me, but it didn’t, it was like having live porn to watch as I was having sex. Well, I guess that’s exactly what it was. Before long, I felt the intense, growing pressure and Monica frigged her clit so we came at the same time. After, she just laid down on top of me, and stayed there until our breathing slowed back to normal and I became flaccid and plopped out. It was a strangely touching moment, as the other two were already getting dressed.
I think I smiled ear to ear for the next day and a half. It was annoying, because I couldn’t stop doing it. Rachel and I broke up a couple weeks later without ever actually having sex. Oh well, right?

My experience with schoolgirls who are more willing than you originally think.

So, I didn’t know what sub was best to put this on so I’m going to try and make this quick but I’d just like to talk about my experience in my school (I’m a student and everyone I’m talking about are students of legal age, if that’s what you’re afraid of).

Now, I live in a relatively conservative place where you would expect a lot of girls to turn down any thoughts or actions that are sexual or romantic in nature. My class has 21 girls and I wouldn’t really consider myself attractive (I’m about a 3/10) but one of my friends dared me to play with both tits of all 21 girls for at least five seconds for within three weeks, one for each day.

I’ve been friends with these girls for years (from one year to eight years) but all of them are at least a 6/10 so I said yes (and there was about $250 on the line). I didn’t know how to bring the subject up to them so I got each of them alone and tried to talk about how awkward this situation I’m in is but I’m trying to dampen the weirdness by saying basically, “But it won’t last long and I won’t be talking about this ever again if you don’t want me to.”

My First Blowjob

I was thirteen in the locker room at school after gym all of us boys were getting dressed and there was this one kid who was talking about blowjobs (and just to be clear I did always kind of find this boy attractive and I’m a boy). All of a sudden he looked at me and said “Hey I’ll give you twenty bucks if you suck my cock”. My first instinct was to say no but I don’t know if it was hormones or if it was just because I thought he was cute but a yes just popped out before I could stop myself. He looked shocked at first but he just said ok and whipped out a decent sized cock (can’t tell you exact size). I kind of just stood there awkwardly until he told me to get on my knees and suck so that’s exactly what I did. I started by putting his dick in my mouth and moved my head back and fourth. Afterwards I took it out of my mouth and began to lick it. I could tell that at this point he was trying to hold back his moans. I started getting into a cycle where I would suck his cock for a while and then I would start to lick it. Eventually while I was sucking it the boy put his hand on the back of my head and shoved his dick deep into my mouth. I wasn’t sure what he was doing at first until he let out a big moan and I could taste his cum in my mouth. Being a little bit in shock I pulled away from him and I spit his cum on floor. After that our gym teacher called from the hall “what’s taking so long in there!” We hurried to clean up and get ready then we rushed out of the locker room. On our way out the boy handed me twenty dollars.

First Intercourse with (M)y Girl(f)riend

This is my recollection of the first time my girlfriend and I had sex. I’m sure my words won’t do it complete justice, but it will hopefully trigger some happy memories for the two of us. Like the previous stories, details have been changed a bit to protect ourselves. So, without further ado, here’s my side of the story.

*****

I was really grateful that we had both gone to the same college, I reflected, as we strolled through the crisp night air back to our hotel room from our night out in our college town downtown. We had been out to drinks with our friends in our annual trek back to re-live our college glory days. It’s always good energy with the group, but I was grateful my girlfriend was on the same wavelength as me as we decided to call it a night, after all, we’d hang with our friends the rest of the weekend. She closed her tab, said our goodbyes, and left the crowds and thumping music of the college scene behind us as we headed back. It was not overly cold out, so we had decided to walk the mile and a half rather than take an uber. It always feels good to stretch your legs after a few drinks, in my opinion. On our way back, we chatted about finally catching up with our friends and the usual small talk, and she revealed she had a surprise for me when we got back to the hotel. I was pretty much instantly hard thinking about what it could be, and revealed that I, too, had a surprise for her.

Camping with my gf and her best friend, but not a threesome.

My gf and I had been planning a camping trip for a couple of weeks, and had invited friends. Some of my friends ended up being delayed a night, but I still made it to the campsite with my gf and her friend, Liz.

I didn’t really like Liz. She was judgemental and rude, and kinda a skank. She was a professional masseuse, but my gf told me she had blown some of her wealthier clients. Not for money, just because they had money.

Anyway, night rolls around and we had been doing a lot of drinking all day. Sitting by the campfire, draining bottles and getting fucked up. Jessica (my gf) was pretty trashed, she was wearing a 2 piece swimsuit and a jean skirt now after being too hot by the fire for any more clothing. Liz was wearing jeans and a hoodie, sitting further away from us and saying generally bitchy things to both of us. But we were all drinking, so it didn’t matter.

Eventually, Jessica says she’s going to sleep and that I should come with her. Liz says she’s coming too, but she keeps bitching about whatever stupid girls bitch about when they get free alcohol. I honestly didn’t care. I have never liked her.

My first blowjob [20m]

So last week I happened to stumble upon an ad on reddit and I replied to it and surprisingly she replied and after some talk we managed to find a night that we were both available to meet up. Unfortunately it was not that comfortable since we both couldn’t host, so we just did the deed in my car.

Was pretty awkward meeting a stranger for a sexual act but she wasn’t into the small talk and so we hopped in the backseat and I pulled down my pants and she got to work immediately. Gosh, that tight and wet sensation of her mouth cupped around my shaft was pretty incredible. I wasn’t allowed to touch her and she didn’t remove any piece of clothing, but that would have probably made me cum faster anyway.

I was breathing deeper and heavier, embarassed that I might cum from just a few minutes of getting head and asked her to slow down. I warned her I might cum soon and she asked me where I wanted to cum, to which I replied in her mouth. She obliged but didn’t want to swallow, which was fine by me.