Confession of a first time gigolo

Here goes my story that I haven't told anyone. I am new to reddit. I have been out of a 5 year long relationship, so really haven't been into the dating scene. I've recently experienced meeting girls in real life randomly who wanted to have sex right off the bat, some within a couple of hours meeting. I don't know what it is, but these random girls claim they never do it, but they immediately felt comfortable around me. For instance, one girl was with a date when I accidentally bumped her with the back of my chair. She told me to wait and came back with her date and told him I was taking her home. Meeting these strangers is exciting and in bed you never know what to expect, different tastes and different needs. All in all, I have found that I am hooked on it, the mystery, the newness, and moreso making a woman explore her sexual fantasies in a no-strings-attached scenario. So I wanted to see what is out there on reddit and found RAOMD. So I posted here on reddit RAOMD last week and I had been to chat with a girl who had never had a guy go down on her, and wanted to experience it for the first time anonymously. She was self-conscious about it, how her pussy would look to me, and apprehensive, but we eventually met up on Thursday night. We met at a hotel and had a drink to smooth her rough edgy nervousness. She was so self-conscious she kept her top on and wore full length crotchless fishnet stockings. We made out, I won't bore with you with the details, unless you want it, but she was totally satisfied. She told me she would tell her friends and possibly get in touch with me if they are interested. The kicker here is she went down to the ATM and handed me $200 bucks and said thank you for your services. I wasn't going to take it, and she wanted to make sure this was a transaction. She looked at me and she said, "You know you like that I'm paying you, just take it." I did. I felt weird and have been thinking about it ever since. A couple of girls I met had jokingly said they knew girlfriends of theirs that would gladly pay for multiple orgasms and incredible sex, specifically with me and I only laughed it off. But this confirms it, I officially and technically a male prostitute as of last Thursday. I am ambivalent. One part of me is proud of it, and the other part of me is ashamed that maybe it's wrong. I took a walk downtown after that experience to clear my head. Can anyone else relate, guys or girls?

My evening with friends girl (20M/19F)

A few years back I had this friend who later on after this story took place I had learned he had stolen money from me. Anyways we were hanging out st his gfs place drinking and just screwing off. He had to run one of our buddies home and told us he would be gone about an hour and a half to two hours. Ki decide just to hang there at the house with his gf and another male roommate.

So he leaves and his gf (Heidi) comes up to me in the kitchen. Little description of Heidi. Heidi was a stripper at a local club. She was about 5'6 and 120 lbs. Long black hair with light skin and brown eyes. Her titties were 34b cups and very perky. Truly a good looking young woman. So she hops up on the counter there. Dressed in short jean shorts and a sleeveless top. Heidi looks me straight in the eye and says hi. I say hi back. She smiles and just kinda stares at me. I ask her what that looks about and what she's thinking. She says I'm thinking about you. I said really? Like what do you mean? Heidi then says; I've been thinking about how much I want you and I wanted you since first time I saw you. I said to her; well that's nice but I don't usually do my buddies girls. She then says as she hops off the counter; well he doesn't need to know now does he! She wraps her arms around me and we start to kiss. A great kiss at that as our tongues explored and I soon felt yes melting into each other. We broke our kiss and she said well that was very nice wasn't it? Yes I replied.. I now had a major hard on for her.

[M]y [F]iancee’s first time with a butt plug

It all started when she mentioned reddit. "So I was reading this post on reddit earlier…" "Oh yeah?" "Yeah, it was about how to make anal good the first time… I think you should read it" My heart started beating faster at this. I looked up the article and started reading. I read a comment saying that sex with a butt plug in felt really good, and asked if she would be interested in that. She said absolutely.

At this point, we went back to watching TV. I was sat in the middle of our couch with her at one end, draping her legs over me. I began idly stroking her legs, moving higher and higher until I was running my hands over her pussy every once in a while. This went on for probably about an hour and a half before the show we were watching ended.

Crazy weekend visiting a friend (MMF)

So I (21 F), visited a high school friend at her university for her 21st birthday a few days ago. I sent out emails to my professors claiming a vague illness and went to stay with her for two nights, both of which turned out to be biiig celebrations. The first night was kind of low key, and one thing led to another and I hooked up with her friend Dean. Dean was pretty good looking, funny, and he lived alone. I went home with him that night and sure enough, we ended up having sex. He was definitely good and I enjoyed myself quite a bit. The next night we celebrated at a few bars near her school. Dean was in the group going out that night and he introduced me to his friend Will. Will was a bit taller than Dean, not as attractive, but also funny and an all around nice guy. Many shots into the night Dean invited me back to his place again. I eagerly accepted the invitation but I noticed Will coming along too. The three of us got back to Dean's place and started watching Archer. We were all drinking, and laughing, and having a pretty good time when Dean texted me from right next to me saying "come help me with something" which I took to mean lets go bang. So long story short, I'm sucking Dean's dick in his room when Will "accidentally" walks in. They kind of smiled at each other and I figured out what their plan was pretty quickly. Being drunk, and horny and in a city I'll most likely never be in again I kind of encouraged it to get the awkwardness out of the way. After a few minutes I was sitting on Dean's bed while they stood in front of me with their erect cocks in my face. Dean was about 6" which I was able to deep throat with some effort, and Will was probably about 5.5" but thick. After sucking both of them for a little while, Dean got behind me and started fucking me while I sucked on Will's cock. about 10 minutes in, they decided to switch places. Will entered me and I came almost immediately. In the 15 minutes that followed I probably came on Will 2 or 3 more times while I took Dean in my mouth. Overall it was kind of clumsy, but it was my first experience being double teamed by two guys and holy shit did I like it.

“I’m Gonna Kill You & Claim Self Defense”

Tired and becoming bored of dealing with AMP's, I decided to switch it up a notch, I got on backpage and began to search for a gorgeous prostitute I could fuck. This was like literally being at a prostitute store, you had an array of options. Black, white, Hispanic,Asian, mixed, Russian, Croatian. I mean L.A. is filled with all types of people. So I finally seen this gorgeous mixed woman who couldn't have been any older than 25. She described herself as being the queen of riding dick, she was also very bragadocious in her ad about her technique. She charged $150.00, so before I contacted her I really thought about it and said to myself, "do you really wanna do this? why don't you go to the AMP get a massage/ HJ and from there call it a day." Then I looked back at her pic and said I gotta try this especially being in LA for a short period. I contacted her by text, transcript is as follows:

*WannaBeSpecOps: Hi, I seen your ad, curious if you're available for a few hours tonight?

*Staci: Hey babe, yeah I'm free, what were you wanting to do?

Memories [M]

Ok, so this isn't a well-crafted story, but I just wanted to describe how my ex and I used to do it sometimes, a few years ago now. It turns me on to remember it. This was back when we both lived with our parents, and opportunities were more scarce. My GF was young, early twenties, petite and quite pretty. She wasn't "perfect", but she definitely got me hot. And she had a bit of a dirty streak. The sort of thing that would happen is this: we'd be sat around in the living room of my parents house on a Saturday (for example). My parents would be around the house, but not right on top of us or anything. My GF would say something like "Shall we go upstairs to your room…?" I would know exactly what she meant and get really excited at the prospect. So naturally we would make our way upstairs to my bedroom, without any fuss, and close the door. Then there'd probably be a conversation along the lines of "we have to be quick and really quiet so your parents don't know", which was absolutely fine by me as I would be so horny I'd just want to fuck. So then we'd get down to it: Usually little to zero foreplay. I'd get my pants and underwear off, already really hard, and a condom out of my wallet, straight onto my penis. While I'm doing this I'm getting even more excited at the sight of her taking her jeans off, or pulling her skirt up to her waist, and her cotton panties falling to her ankles, or panties sometimes just pulled to one side. Then she'd either lie back on the bed, or get on all fours on the bed, and give me a look as if to say "what are you waiting for?". Can you imagine how horny I'd be having this elicit encounter with my young girlfriend in the middle of the day? The sight of her naked lower body. Her pale goosebumped skin. The hairy mound between her parted legs. We'd usually both still be wearing our top half clothing. There might be a quick bit of kissing and fumbling, or sometimes I would put my tongue between her legs for a minute or two. I might unclasp her bra underneath her T-shirt without taking it off and quickly fondle her soft breasts and hard nipples. But mostly it was about the fucking. I'd enter her bit by bit at first (no artificial lube required…) and then start to pump rhythmically and deeply, but not with so much force or speed so as to make any noise. Quite possibly I'd be overhearing my parents talking elsewhere in the house. No, I wouldn't make a sound, but my girlfriend would know I was horny as hell. My rock hard penis and my urgent thrusting told her that much. All I would know from her in return would be the quick, shallow breaths she would take, her closed eyes, her open lips, her natural wetness between her legs and the pink flush spreading down her neck. So we would fuck like that, quietly, urgently, and to be honest it would probably be less than five minutes (or even considerably shorter: I was a young guy, and so turned on) before I would feel the tightening in my balls and I would fill up the condom, utterly fulfilled. I'm pretty sure my GF would enjoy these encounters too. Sometimes I would gently finger her afterwards until she came, quietly. But she didn't always want to if she was anxious about parents being around. All in all these experiences were so fucking sexy precisely because we had to be quick and quiet. Sometimes I wish I could still have that kind of sex, but it's no longer necessary, unfortunately!

A 60yo sucked (m/m)y 18yo cock

I'd just turned 18 (like literally less than a week before). I'd been taking classes in the evening and it was winter so the sun was setting even as i went to class. That summer I'd basically realised that I was bi and that I actually really got turned on by dick as much as I did by pussy. I was an absolute horny wreck of a teenager and even though I was tall and attractive I'd never even so much as kissed a girl, let alone done anything with a guy. but god did i want to. I stumbled across the craigslist scene (hot) and then discovered a list of local cruising locations. I was horny and an exhibitionist and often after class I'd take my clothes off in the car and sit there wanking for a good 40 minutes. So this one night I get to class and I'm the only one there. The lecturer turns up and waits for ten minutes and then basically tells me to go home. Now I know theres a cruisey bathroom only 5 minutes from campus and my parents aren't expecting me home for over two hours so I start to get kind of excited. I get to my car and pull my pants down and I'm so hard sitting there in the dark that I just think 'fuck its worth a look' and drive off. The toilets are in a not very well lit park and barbecue area next to the lake, so I park and get out to have a walk around. I sit at a picnic table for a bit and watch some yummy mummy jogger go by and I think to myself if she knew what i was here for lol ;) I go into the toilets for a bit, noones there unfortunately, I take my pants off and start stroking, I've never been harder. Nothing seems to be happening though so reluctantly I zip up and head out the door. I dont wanna leave yet though, I'm still so horny and theres the chance that i could actually finally get off with someone for the first time. So I walk over to the lakefront and follow the shore a bit until I'm standing in a dark grove of trees and i unbutton my jeans and let them fall to the ground, looking over the water to the city with my cock rock hard and hot against the cool winter air. I notice someone coming my way, and I hastily zip up and start walking back to the car, scared that I was almost busted. But then I make what turned out to be a fateful decision. I desperately want to cum by now and I know I wont be able to at home, so I decide to go to the bathroom one final time and at least shoot my load. I go into one of the stalls and start masturbating facing the door, and i can see the shadow of my hand on my dick creep under the crack of the door. And then I hear someone else come in. Itll just be someone wanting to pee I think, they couldn't possibly want me, nothings going to happen. But god i couldnt help myself, moving forward just a bit so the shadow of my cock poked under the door, so that this guy could see it, wanting, wishing that this guy could see it. he goes into the disabled cubicle, and im thinking again 'nothings gonna happen, just blow your load and go' but my hearts racing already, what if? and then I hear it. "do you want it sucked?" I look around and look this guy dead in the eyes over the partition. hes gotta be 60 at least. OH GOD YES I want to scream but all I can manage is a nod of the head. "unlock the door". and then he's in the cubicle with me on his knees, and I feel his hand around my cock, and I know this is actually gonna happen. He looks at me and in one smooth motion my shaft goes into his warm, wet mouth, my first warm wet mouth. and god does it feel good, his lips bobbing up and down on my dick and his beard scratching my balls, I run my hands through his silver hair as he runs his over my ass and under my shirt and up my chest. I'm in ecstasy and stifling my moans and in a few minutes all i can do is whisper I'm gonna cum and he tells me to do it in his mouth and ohmygod yes I grab his head and pull his lips right to the base of my shaft as my load erupts. I'm shaking and all i can manage to say is 'thankyou' as i zip up and run out of the toilet.

losing my virginity (M/M)

Unaccustomed with my own sexuality, I am fairly inexperienced. Before going to college, I had never kissed or done anything with another person in a sexual manner. It was sophomore year in college where I had my sexual awakening. Drinking too much beer, with the addition of spin the bottle, landed me my first kiss with both genders. As I slowly discover that I had a strong affinity towards men, but I wasn’t quite ready to lose my virginity yet. I became extremely sexually frustrated as my sophomore year was coming to an end.

(F)irst threesome with a married couple :D

Hey all! I havent shared this story publicly yet, but if you've been nice enough to PM me after some of my other posts you might have heard it ;) After a good response by several people, someone special told me I should write it up and post it here! Its the story of my first threesome!

So about 2 months or so ago, before I posted on GoneWild, I sent a message to this really cute couple on Couples GW that was looking to chat with a younger girl. They were super sexy, and we talked for a few weeks trading pictures and talking dirty. After a couple weeks, we found out that we live 30 minutes away from one another!

The couple invited me to dinner and drinks one Friday (they explicitly said just dinner/drinks, no funny business :P). I got to the restaurant, which I had never heard of, and it was quite fancy. I was wearing a kinda skimpy black dress and had matching black panties/bra to match! They both looked super cute too, the wife had a blue and yellow dress on with these amazing heels, and the guy had on a black dress shirt tucked into white dress pants.

(F)irst Ti (m)e Anal with my Husband

My husband and I have been married for a little over 5 years now and overall we have a good sex life. He is a very caring lover and always makes sure I cum when we have sex. Today though, my eyes were opened to something I thought I'd never try.

I've watched a little porn and some of it had anal in it, but I never thought it would be something I'd enjoy. Looks good on the Internet of course but that can be deceiving.

Now my husband is over average size, just a little over 9 inches and a good thickness. Another reason I wasn't ever going to try anything like ass play with him. Today changed all of that.

Last night I had been reading some stories here, watching some videos and was feeling a little naughty. I sent some flirty texts to him (he works a late shift) and sent him a sexy picture. After that I went back to one of my go to videos and started to play with myself. I was soaking wet from both the video and thinking about my husband's cock filling my pussy up. I'm fingering my dripping pussy and rubbing my clit and eventually I cum. Once I wash up, I head to sleep.