[M]y [F]irst time didn’t exactly go as I expected

Hello everyone. I wanted to share the story about how I lost my virginity. This story is all about Janet. Until it wasn’t.

Let me explain. This took place about 4 years ago when I was a 26 year old. I know there are others out there that are 26 & non-sexed, but I was brainwashed by the cult I grew up in. We had been told that sex outside of marriage was bad and until your arranged marriage even touching your cock would spiritually cripple you and fuck up your life! When I was 21, I finally came to my senses through a series of events that I will not bore you with and broke away from my cult and tentatively entered normal society. But I was socially inept, especially with girls (in addition to not touching your willie, you weren’t even allowed to talk to girls. When I was a teen, I got yelled at for thanking my sister’s friend for not closing a door on me. For real.). I didn’t know how to dress, how to act in normal society. In some ways I was a freaking baby. And since when I finally got access to TV and movies my favorites were Adam Sandler type movies, I was just further fucked in the head when it came to how to act around women.

But I finally started to learn. And I had slowly started to shape my body and my appearance into that of a pretty decent looking guy, if I could say so myself. Finally, there I was at 26, in my last semester at a commuter college while I worked full time at a chain fast casual restaurant about a block away, finally starting to act at ease around women, even the attractive ones.

One of those attractive ones was Janet. Janet and I had been working together for about three years and if there was a real life dream girl for me, Janet was it. She hit all of my likes–dark hair with light colored eyes (check!), slim, athletic body (check!), a bit of a booty (check!), a rebellious streak (check!). Janet was about 5″6, slim with long brown hair that she enhanced with various colors during the time I knew her, light blue eyes that were almost almond shaped. She had a bunch of tattoos that I had glimpsed when we were in a group out, and there was a strong rumor that her clitoris was pierced, which seemed incredibly hot to me for reasons I couldn’t articulate.

Anyway, after almost three years together with being casual work buddies who maybe know a few things about each other but that’s it, we ended up taking a class together at our college, a low level playwriting class that I had taken on a lark and totally not at all because I had heard her mention it to a co-worker. Do I sound like a stalker? Totally a coincidence, that’s all. Honest. We worked together on the major class project and really hit it off. Now Janet wasn’t just this super hot chick that I worked with, but a fully formed individual who was funny and had some similar interests and also hated religion as much as I did. Bonus!

All the work we did together was at the school’s library or student center (there were two other people in our group) and after we handed in the paper, she told she had Netflix and was planning on watching a few Tom Cruise movies, did I want to come over? Putting aside my deep non-gay love for Tom Cruise, I immediately decided that vibe I was getting was one that was sexual. According to my super long history of reading cues from women, I had noticed her giving me small touches on the arm, side glances and grins, and I really thought I had won her over and as a reward for being an awesome partner she was going to have sex with me. Because that’s how life happens!

So I told her absolutely in a totally casual way and spent the rest of the day thinking about how I was finally going to have sex. I cleaned myself up at home, put two more condoms in my wallet (yes, I always carried one with me. And yes, condoms were one of my first purchases after I left my cult behind for good, because I honestly thought normal life was like the two porno magazines I had seen) and told my annoying 40 year old lesbian roommate not to wait up for me and headed for Janet’s.

I felt it was important not to seem too eager, so I showed up twenty minutes after the time we had agreed on. When I got there, she invited me in and gave me a nice hug. She was wearing a thin blue t-shirt almost the same color as her eyes and black short shorts and I had to will my raging boner down as she led me in. We turned the corner from the hall to the dimly lit living room and I saw two small couches arranged at a 90 degree angle around a huge TV that was showing the classic Tom Cruise car racing movie Days of Thunder. On one was a chubby girl and on the other was a handsome adonis of a man, both in their twenties. “This is my roommate Amy,” Janet said, nodding at the girl, who smiled and nodded at me. “And this is my boyfriend Ricardo.” The adonis gave me a half-hearted wave, while watching the exciting flick.

Of course a super hot girl like Janet had a boyfriend. And of course he was fifty million times hotter and more masculine as me. And of course I had blown through every possible social cue that Janet had given me that she just wanted to be friends (when I thought back, they were definitely there). I was lucky that no one was looking at me, because I must have looked like I did when I realized god didn’t exist and that abstaining from bacon and shellfish and masturbation wasn’t going to get me a kick-ass afterlife, which is to say, the look on my face was one of pure anguish. Janet went over to Ricardo and snuggled into him on the couch, and I recovered enough so that when she looked over to me and told me that there was beer, soda and snacks on the kitchen table, I didn’t look like someone had been kicking me in the nutsack over and over. I thanked her, grabbed a beer and some chips and perched on the edge of the couch that Amy was sitting on, as far away as possible without falling off.

I sat silently watching the movie, but also looking at Ricardo and Janet out of the corner of my eye, feeling incredibly horny and frustrated. Ricardo was leaning against the arm of the couch, facing the TV and Janet was leaning back into him, between his legs. It was pretty dark in the room, but I realized that Ricardo had his hand down Janet’s shorts and was fingering her. I watched glumly as her hand snuck behind her, likely to return the favor to her boyfriend. Amy got up a few times to grab another beer or food, walking around the TV to do so. Or maybe she was getting up to get a better look of her roommate and boyfriend giving each other hand jobs, I don’t know.

It was about 9 when the movie ended and Amy popped off the couch and went to turn on the lights. I could see Janet and Ricardo quickly moving around and when the lights came on, they were sitting next to each other, the hands in their own laps, no evidence of the sexual pleasure they were giving each other, besides Janet’s flushed face and the wet spot on Ricardo’s t-shirt where he had wiped his wet finger off.

“Uh, I think I might be coming down with something, Mike,” she told me apologetically. “I think I should go to bed. Maybe we should reschedule this, OK?”

I nodded and thanked her for inviting me and she stood up and headed quickly towards the backroom. Amy and I were staring at Ricardo, both expecting him to follow his girlfriend, and he looked back at us guiltily. He shifted around in a way that made it clear he was trying to figure out how to get up without us seeing his erection until he finally blurted out, “is that a bird in the kitchen?” Amy and I both looked away and Ricardo sprung up and raced after his girlfriend, slamming the door behind him.

I could hear giggling coming from their room, and Amy looked at me and gave me a lopsided grin and got up to turn off the TV. I looked her over for the first time. Yes, she was a little on the chubby side, but she looked pretty cute with short blonde hair, a little button nose, hazel eyes, curves on display in a cleavage bearing tan tank top and loose purple pj pants. She came back to the couch and looked at me. “Don’t feel too bad, Ricardo goes to school out of state and just showed up like twenty minutes before the movie. Janet was as surprised as you looked as you came in,” she said with a chuckle. “Not that you were going to get laid even if he wasn’t here.”

I started to protest but she laughed. “Don’t worry, I’m not judging. You aren’t the first guy that Janet brought home who maybe thought they had a chance with her and didn’t. But that look on your face when you saw Ricardo, man. I wanted to laugh but you looked like a lost puppy.” She covered her mouth to keep a laugh down, but was unsuccessful, snorting a bit, and then laughing. “Sorry,” she said, kindly.

I laughed along with her and relaxed a bit. We talked for a few minutes, as sexual sounds started to emerge from Janet’s room. I had been working on getting my penis to go back to sleep so I could leave gracefully–I didn’t think the bird in the kitchen line would work twice–but as soon as I heard Janet’s low moaning, my boner sprang right back to attention, foiling my plan.

“So what’s with your weird accent? Are you an immigrant?” she asked.

“No, all American, just from a weird part,” I said vaguely.

“Well Mr. All American, you can stick around if you want and enjoy the show or whatever,” Amy said. I blushed and she giggled again. I enjoyed listening to her light girlish giggle. “You are totally hard aren’t you?”

I nodded and blurted out, “and I’ve never done it before” and then got even redder.

Amy just stared at me. “Really?” I just nodded. “What are you? 23? 24”?

“No, 26,” I said.

“Wow. Are you like saving yourself for marriage or something?”

I shook my head gloomily and gave her the Cliff Notes version of my life, finishing up by explaining that I just didn’t know how to act around girls.

“Well, you are a little awkward. That perching on the end of the couch thing, for one. Telling me your a virgin too. Here,” Amy said, patting the couch next to her. “Come sit next to me normally. I’m not going to have sex with you, but you can at least be more comfortable.”

So I moved closer to her and we had a nice long conversation, our knees inches away from each other. The proximity meant I was having trouble getting my dick to finally let up. After about forty minutes, the sex noises had ceased and Ricardo came out, wearing only boxer briefs. Amy openly gawked and I too was thinking sadly that there’s no way Janet would ever want to fuck me when she was getting that. The three of us talked for a little longer–he was actually a really nice guy and even apologized for making the night awkward–and then I left, still crazy horny but with Amy and I making a date for a few days, although I did have to listen to my annoying lesbian roommate make fun of my big mistake.

Amy and I went out a few times and besides from her giving me a handjob once in my car at 2 AM in a sketchy neighborhood, we didn’t do much more than a little kissing, which was still more than I had ever done. It took all my power to not prematurely ejaculate every time we touched, which was often because she was the type of person who was always hugging or touching. She looked good when she was wearing makeup and not just wearing around the house stuff. She was clearly waiting and I tried not to push it because I figured the last thing that would get me sex was acting like a horny dick.

Two weeks after we met, and for our fourth date, I came by to pick up Amy to go to see some obscure band that she was obsessed with. I texted her to come down, like usual, but she told me she was running behind and I should come up. A little annoyed–my dad was always crazy anal about being on time for stuff and it unfortunately rubbed off on me–I knocked on her door. Amy answered it completely nude.

I stood in the hallway gawking at her big, full breasts, her dark red areolas and hard nipples, her creamy white skin, and especially at her neatly trimmed pubic hair.

“So how about you come in here?” she said with a smile. I was instantly hard and my dick lead the way. We started making out as soon as the door closed. “I felt like I was ready to pop your cherry,” Amy told me between kisses. She pulled me towards her room and we stumbled back there, still making out. As soon as we got in her room, she pulled my clothes off and I grabbed one of my magical condoms from my wallet. She guided me to the bed and said we needed to make sure I was completely hard and got down on her knees and started to give me a blowjob. I wanted to be a stud and fuck her brains out without blowing my load, but that was never going to happen with her tongue arching its way over my dick, so I pulled her up and she rolled on the condom and we fell onto the bed, her on her back. I unsuccessfully tried to ram my way in and Amy took over and guided me into her wet pussy. We both groaned with pleasure and I thrusted one, two, three times and suddenly wondered if Janet was home and could hear us and then…that was it.

“Fuuuuuuuck,” I said mournfully as I came. Back in my religious days, I remember a friend of mine who had five older brothers tell me that the first time is always quick. But there’s quick and then there’s 5 seconds and pop. I collapsed next to Amy, not even enjoying my orgasm, feeling shame, but she just hugged me and gave me a kiss on my cheek.

She told me to go to the bathroom and clean off and not to worry, no one else was home. When I got back, she had put on a emerald colored halter top and a loose black skirt that ended midthigh. I once again failed to hide my disappointment that more sex wasn’t in the offing, but Amy gave me a kiss and said Janet had gone to visit Ricardo so if I was a good boy, we could have more fun later.

We drove to the show, which was in a dive bar packed with hipsters and an assortment of motley losers like myself. I hadn’t seen that many beards in one room since back in my cult days. The band was pretty crappy in my opinion, a bunch of depressed looking guys on heroin or maybe they were depressed dudes who just looked like they were on heroin, or maybe both. But Amy was enjoying herself, dancing around, bumping against me, almost popping out of her shirt a few times. That was at least enjoyable, as was when they played some slow jam and Amy had me wrap my hands around her and she swayed, while grinding into my cock.

I also made many trips to the bar for her and by the time the show ended, she was good and plastered. The whole three block walk to my car she was grabbing me, having me grab her and stopping for long kisses. As soon as we got in my car, she leaned over and we started making out. There were people walking by on the dark side street, but she guided one hand under her shirt and my other hand under her skirt, where I realized she wasn’t wearing underwear. I nervously poked at her wet pussy as I rubbed her hard nipples and cupped her breasts as we kissed.

“I want your cock in me,” she moaned, “but I also want to cum right now. The faster you get me there, the faster we’ll be back to fucking.” I increased my enthusiasm in finger fucking her, using two fingers and pushing them against her clit and deep into her. I kissed her neck, her ears, her shoulder, and felt her moan and squirm. Her hand joined mine under her skirt and she guided me to the places that were best for her, squeezing her thighs against my hand. My work finally paid off as she leaned hard into me, almost crushing my hand and cumming so loudly that an older couple walking by the car stopped short and looked around.

“Oh that was great,” Amy said, breathing heavily and smiling at me. My shoulders were hurting from the awkward position, and I removed my hand from her shirt and was taking my other hand, which was pretty wet as was the cloth passenger seat, out from under her skirt, but Amy grabbed it and started licking my fingers. “Oh, I love the way my pussy tastes,” she purred and I just about blew my load. She offered me a taste and I nodded enthusiastically as I tasted the musky juices for the first time.

My hand finally clean enough to drive, I drove home quicker than the law allows and politely turned down multiple offers for head while driving. We made it to her place and I briefly believed in god again when there was a spot open exactly in front of her building. “If the elevator’s empty, we might just have to fuck there,” Amy whispered as we got out, but unfortunately for me there were three other people waiting when we got there.

Once we made it to the apartment, I grabbed Amy from behind as she started unlocking the door. I grabbed her tits with both hands and kissed her neck, rubbing my erection against her juicy ass. She fumbled with the key but finally unlocked the door and we stumbled into the small hallway and made it to the dark living room. Amy braced herself against the wall, sticking her ass out at me. I leaned against her, kissing her and fumbling with my pants.

“Just shove it in, I need your cock,” she moaned. “Fuck me hard.” My brain was no longer functioning properly and I finally unbuckled my belt and pulled my pants down as she was grinding against me. I maneuvered my hard dick past her ass cheeks and was able to slip into her wet vagina. I grabbed her hips and pounded her hard and she pushed down, keeping my dick in her.

Amy’s face was flush and she was loudly enjoying our activity. She was so wet and loose it felt like my dick was in a cup of water, but she was fingering herself as I pumped hard, her short skirt flapping against me. I was tiring quickly and was about to suggest we move to her room when her volume increased and I felt the muscles in her vagina grab my dick like nothing I had ever felt before. She had her orgasm loud enough to wake the people across the street and I could feel her dripping down.

Amy moved off the wall, and grabbed my hand, dragging me into her room. “Want me to take off my clothes or leave them on?” she asked.

“Leave them on,” I told her. She got onto the bed, wiggling her ass at me. “No, get on your back.” I moved towards her, shedding my clothes and slid my now condomed dick back into her. I pulled her tits out of her shirt and fondled and sucked them. “Talk dirty to me,” I asked. Amy told me all about what my cock was to her and what she wanted me to do to her and as she was describing some act only gymnasts could pull off, I had my most excellent orgasm ever. I fell on her, sweaty and happy.

Three weeks later, we were married.

Source: reddit.com/r/gonewildstories/comments/8d8vsp/my_first_time_didnt_exactly_go_as_i_expected