I lost my virginity to a 50 year old [MF]

I grew up super prude and when I was 18, almost 19, I decided I needed to just get it over with. Virginity had been holding something over my head for so long.

I made such a bad choice. I met a man who was super kinky. And for some reason, I let him play me. I went along with it for some reason? Part of me is like YOLO and it’s not that deep. Part of me feels hella guilty.

I agreed to meet him in person. Made sure to tell a friend where I was. I gave him a two hour blowjob. My first one ever. I actually liked it. We ended up having sex. Remember this is the first time I had met him in person. It was so so stupid but I wasn’t really in my head. So yeah. Was 18 and lost it to a 50 year old.

I feel super guilty about it now, but I figured that it’s a “gone wild” story if I’ve ever heard one. Just needed to put it out there!

An Unplanned Threesome [FMM]

By my Junior year of college, I felt I was pretty well set, sexually. To my young mind, anything two people could do together, I’d either done it, or I wasn’t interested. I was cool, collected, thoroughly in charge of myself. I had a very respectable collection of FWBs that I could rely on at pretty much any time to scratch any itch I may have.

One afternoon, I was relaxing with one of my FWBs, who was a bit heavier on the “friends” part than most. Kyle was as casual about sex as anyone I’d ever met. He was, of course, always happy to satisfy my desires, and he was more than capable, but if we got together and just talked or watched TV, that was fine, too. His roommate, Bill, was the exact opposite: high strung, desperate, a walking hardon always on the verge of a panic attack. This particular afternoon, Bill was out doing whatever Bill did with his afternoons, while Kyle and I were laying on his bed, watching TV. About an hour in, I got a bit impatient. I enjoyed watching TV with Kyle, I enjoyed talking with him about whatever happened to be on, but I’d come over on my afternoon off with intent. So, being the little spoon, I started grinding gently against his crotch. Kyle wasn’t one to chomp at the bit, but he certainly knew how to rise to the occasion. In no time, he was pushing back against me, his hard dick pressing between my cheeks. He snaked a hand up my shirt and pulled my bra down, grabbing one of my tits and pinching my nipple between his fingers. He knew exactly how to turn me on.

[MF] My Mom’s Friend Was A Massage Therapist (PART TWO)

[PART ONE](https://www.reddit.com/r/gonewildstories/comments/axbnzq/mf_all_stories_have_a_happy_ending_my_moms_friend/)

After getting a nice release (and life advice) from Christine, I truly did change my life. It was like her stroking my dick made me hungry for success. Or maybe not even success. Just hungry for something more than I was getting. I put together a 6-month plan. I would work my ass off, save my money, and then move to the West Coast to chase my dreams.

And I did it…kinda. The 6-month plan turned into 10 months, but you can’t win ’em all. I was just happy that I finally did something with my life. I was motivated like never before, and as silly as it fucking sounds, it was all because of Christine. My mom wanted to have a going away dinner for me a few weeks before I was scheduled to leave, so I knew I would have the chance to thank Christine then. In the past nine months, I had only talked to her a handful of times because I was busy working most of the time.

The Locker Room [group]

My sophomore year of college, I was the only girl on the club soccer team. This was never really a problem though because everyone was respectful and I felt like one of the guys (and it helped that I was the team’s top scorer). The guys on the team were pretty hot I guess (I have a thing for athletes), but I had never really thought about it before.

Like many club teams, the school sponsors the team but doesn’t provide a coach, so we had a senior in charge I’ll call Mike. It was our last road game of the season against a time team in the next state over. We had played earlier in the season, and for some stupid reason, the women’s visiting locker room is about a mile away from the men’s (don’t ask me why because I will never understand). While on the ride over, I was bitching about how I had to walk to the other side of the campus last time and everyone agreed that it was dumb.

Getting Help Shaving & Sex Lesson from College Roommate [FF] [shaving] [virginity]

Getting Help Shaving & Sex Lesson from College Roommate

*Ugh*. I look down between my legs, razor shaking in my right hand. I turned the shower off and lathered up the area in the special clear gel I got just for this purpose. *Louis should feel lucky I put in all this work for him*. I worked on a group project at the beginning of the semester with him, and a few days after we presented he texted me asking me out. We got coffee and I really liked him. Tonight he invited me to his dorm to make me dinner. Unlike me, he has his own room in the quad separating him from his roommates. I don’t expect to sleep with him (and bring up the topic of my virginity) but I think we might fool around a little. However, I’ve never shaved my public hair, just trimmed it. I want to look extra good tonight just in case, but I’m scared of hurting myself.

The good old days of Tumblr [M, MMF, voy, cuck]

Travelling for work, you never know what kind of internet access you’ll have or if you can trust who’s monitoring it. It pays to have a “wank bank” of porn on a UBS key for those lonely nights when you’re in the hotel room, alone, and you can’t sleep. Me, I’m a little old school: images not video. Amature not professional. Mature not nubile. Tumblr accounts that hoovered up postings couples made, posts of photos taken during semi drunken encounters or fantasy fulfilment escapades always turned me on. The cuckold husband. The hotwife. The old friends who decided life was boring, youth has escaped them and reputation be damned they were going to have fun and show the world what they were capable of. I had my favorite accounts, kept them up to date, knew the ones that were trusted by those who made content and those who craved it. I would scan through them, imagining myself amongst the action. Being the stunt cock in the mix, there for the fun but a side attraction for the main event that was hedonism and infidelity in action.

THE NIGHT I BECAME A COCKSUCKER…

**I had met Cindy about four weeks ago and we had a few dates so far, going to a movie one night, dinner another, Netflix and pizza at home a couple of times. I found myself really liking her and enjoying her company. Intelligent and funny, she was about 5’6″ with a slim, petite figure. Her breasts were small, but I’ve always liked that and found them a huge turn on. Her hair is best described as raven black which I found particularly attractive, it matched her eyes perfectly.**

**We were on our fifth or sixth date, having a few drinks at the bar in the local pub, talking about this and that when Cindy suddenly changed the subject to sex, and asked me in a very dramatic fashion,**

**”So, John, have you ever had sex with a man?”, she asked bluntly.**

**I was so surprised by the question I just stammered out that I had not.**

**”Have you ever thought about it? Are you interested?”, she continued.**

Bath fun and oral with me [F] and my boyfriend [M] TESSA UPDATE TO: getting eaten out for the first time ??

Hi everyone!!! Hope you all are doing well :) your girl is back with another story haha, I hope you guys like it!!

Also hi, if you’re new here!! My names Tessa and I write stories about me and my boyfriend Ashton :) they’re all real and not always super amazing, but people seem to love them so here they are!!

Our descriptions:

Me (Tessa): 20, golden brown/blonde hair, blue/grey eyes, 5’5, tan-ish skin
Him (Ashton): 23, 6,6, dark brown hair, green eyes, deep deep voice, some tattoos, muscular

I’m a virgin and he’s the opposite (very experienced, like very very). If you want to read more about what we’ve done, I’ve written about him going down on me, us touching ourselves together, me giving him a blowjob for the first time, giving each other oral in the shower and him using a vibrator on me.

My BF and his inner demon (M/F)

We had been together for a short time but had known each other for years. He was this tall strapping man who id fallen in love with, I was a shorter busty girl. I had been in a pretty rough relationship, and he had stuck by my side the whole time and that’s when I realized I loved him. Through my past relationships I had been able to hold onto my virginity, and it was only when he and I started dating did the stories start to come to me. Some of my friends would come to me and say “you’re so lucky… he’s a real man both physically and sexually”. At first I didn’t understand what they meant but it was when I was asked “how can you take him, he’s so full of sexual drive?” Did I realize that maybe he had another side I hadn’t met. That day it was all I could think about, and it even made me a little wet… That’s when I hatched my plan, that night I sent him a snapchat of me fully clothed. He quickly messaged back “oh hey sorry I was doing homework”, then I turned it up, a snapchat of me without a shirt in a bra and I thought to myself “I think he’s a boob man, either way I have plenty of both”. He, being his typical self, simply answered back with a snap of him self smiling saying “cute babe”. It was in my next snap he realized what I was doing, this time I sent him a video of me in my bed slowly lowering my bra strap. His response was of a snap of his face giving a stern look that turned me on. Without a second thought I sent him a cute picture of me holding my boobs with no visible nipple, and with a devilish grin I hit send. He’d open it and wouldn’t reply for a view minutes. I simply assumed he was rushing through the homework he’d been doing to pay attention to me. That’s when I got a snap in reply, of my bed room window, he was out side my house. I looked out my window which was on the ground floor to see him standing there. I dropped my hands from my chest, yet he never broke eye contact with me. I opened the window and let him step through, I hadn’t got to the part of removing my sweat pants but he pushed up against me grabbing a handful of my ass. He began to kiss me gingerly like he would in the hall ways of the school. But soon enough he changed, there was a force behind him the pushed me onto my bed with him on top of me. I had to push him away only for a minute to shush him, my family was home and if he was caught fucking me we’d both be dead. He would rip my sweats and the pair of boxers I stole from his room off and begin to use my thighs as ear muffs from my own moans. I could tell he was only showing me a small bit of what he could do with his tongue, had he given it his all I knew I would be cumming in seconds and screaming bloody murder. Then it happened, he gave me my first orgasm, he must have realized what was happening as right when it happened his hand covered my mouth, but his fingers kept working on my clit. I remember getting dizzy from my first high of orgasm. That’s when he straddled me, and in a stern voice that soaked me so bad my bed sheets would never be dry again, he told me to pull his cock out myself. I slowly reached up to undo his belt and pulled out the cock that would cause me to be bed ridden the next day from a lack of being able to walk. I didn’t know much of giving a blowjob seeing as that I did it once and I couldn’t make my ex cum. I tried my best taking him to the back of my throat being as far as I could go without gagging too bad to alert anyone else in the house. After about 5 minutes he began to scoot down and stand on the floor, he pulled my body to the edge of the bed and spread my legs. He would tease me by running the head of his cock against me. Finally he began to push inside me as he kissed me making me moan into his lips. It was so intense I remember every muscle in my body squeezing and subconsciously running my finger nails down his back. He slowly rocked his hips as we kept up the make out session. With his hand clasping my mouth each time I began to orgasm. This continued until dawn… hours of nothing but passionate sex. We had school the next day so 15 minutes before my moms alarm clock went off he was climbing out my window. And that’s when I saw the scratch marks down his back, from my bed and in a weak tired voice “oh baby your back”. With a smile that sent chills done my spine he looked at me with a smile saying “wait until I don’t have to worry about noise”. With that and a quick “I love you” he left. My mother would soon come in to wake me up, and of course my body temperature was raised so I faked a sickness to get out of stumbling around school. That whole day I laid in bed a dreamt of him… and the demon inside.

[MF] Awesome Time with Cougar Part 2

So about 5 months ago, I met a 61 year old cougar on a dating app. I am (or was) a 27 year old black male virgin. See post history for details. She invited me over for a blowjob 2 times and told me the next time she would take my virginity. Well I kind of got cold feet and haven’t contacted her for months, until this week. I messaged her and ask if we can see each other again. Lo and behold, she is totally DTF, and wants to be my teacher.