How I ended up having anal sex with a girl before PIV (Interracial, Virgins, Long) [m18/f18]

So some disclaimers: this is long and will take a while to get to the sexual stuff. I have changed some superficial details and names to protect identities but otherwise this is a completely true story of my first sexual experiences and how I ended up having anal sex with a girl before I’d had PIV sex. I am not a writer of any description and this is my first attempt at a story so be gentle. Also, be assured that there is no Loch Ness Monster. Look for the break if you want to skip to where things get sexual.

I left high school a virgin. Not just a virgin, but a never been kissed virgin. Girls wouldn’t just turn me down, they seemed to be a bit insulted that I thought I had a chance. I was short, pale, and geeky. I had acne, braces and was painfully shy. I went off to University aged 18 with my acne gone and braces removed. Regardless, I had built up a lot of insecurities about my attractiveness. Girls didn’t seem to be horrified by me anymore but I was still no girl’s fantasy. A solid 5 out of 10. But that was ok, I had long since made peace with the fact that I was no model. My confidence slowly grew from nothing to still almost non-existent but something. I went on a few casual dates and even kissed a couple of girls, but never got any further than that.

The teasing girl [M/F] (part 2)

[Part 1](https://www.reddit.com/r/eroticliterature/comments/4tqo5u/the_teasing_girl_mf_part_1/)

The next morning, we do not talk at all about what happened yersterday. I have to leave after breakfeast, and I won’t see my girlfriend again until tomorow evening. After leaving her house I directly go to work. I don’t really think about the chastity belt until the middle of the day, when a sexual thought pass through my mind. It doesn’t hurt or block my mouvements, and the sensation don’t bother me to much. But it affect me on the psychological level : I’m not really sure about what I accepted and what is her plan. I don’t even know what it like feel to stop mastubation. More than anything else, the idea she is in complete control of my genitals gives me a very strange emotion. I can’t really explain it, but it’s strong and it won’t leaves my mind. I realise this thinking start to turn me on. The pressure inside the belt increase a lot, as my dick can’t grow like it normally do. One of my co-worker call me. I have to walk to join her, but I have an erection… after two or three seconds I understand no one will be able to see it as my dick can’t change it’s shape. When I walk toward my co-worker I feel the pressure of my dick against the belt at every step. The person who requested my help is a young red-haired woman to whm I alwais have been attracted. While talking to her my erection only gets stronger. Why of all my co-worker did it need to be her ? I have so much difficulties concentrating that she ask me if I’m OK, to what I respond I’m a little tired.

The teasing girl [M/F] (part 1)

**It’s the first time I post here and I’m not a native english speaker, so excuse me if I make mistakes.**

I [M,20,virgin] have a new girlfriend and our relation is going well. She [F,20] have a lot more experience than me in relationships and have had several sexual partners. She also have a beautiful body with a D cup and a nice ass. I’m pretty sure she noticed I’m looking a lot at her body, and that she is purposely helping me doing that with positions that show her curves while acting like she didn’t notice. This little game started two weeks ago, and now we’re getting more intimate and start to talk about sexual topics, though never referring to ourselves.

Hot lecture theatre sex with horny, wet classmate [M/F]

Made an account just to share this story, which occurred during my second year of university with a fellow classmate.

She had all the guys completely wrapped around her finger, with us begging her to wrap her lips around our dick. She was amazingly beautiful, in the most innocent sense. Long, curly hair, eyes that could make you hard by staring into them, and a beautiful face. Her cheekbones were wonderfully sculptured, she had a very cutting jaw line, and she had, overall, a wonderful figure fitting her 5 ft 3″ frame.

How to Discipline a Bitch

There was this guy at work… he was driving me crazy! We were working together on the same project and I was feeling like I couldn’t stand him anymore. He would always second guess my decisions, contradict my opinions, and that arrogant look on his face was the most annoying thing in the world. The fact that he looked like a lingerie model was not helping, either. Our project was bound to be a total failure, and I had been really stressed about it for several weeks.

Even my relationship with Sir was starting to feel the consequences of being around the gorgeous asshole all the time… Sir always makes sure to take the pressure off my shoulders whenever I need it the most, by giving me a well-deserved spanking and then choking me until I cry with His thick cock. But He noticed something serious was going on inside my kinky head this time, so after violently face-fucking me, He took me into His lap and asked me in a gentle voice:

“What’s wrong, little one? You don’t seem like yourself lately.”

“Well…Sir, I don’t want to upset You…”

“You won’t, I’m all ears!”

My Girl[f]riend gets comfortable with my room[m]ate

My girlfriend Lauren (22/F) was hanging out at my place, drinking with me (26/M) and my roommate Sam (28/M) at the time. Lauren was(is) probably 5’2″ and 110 lbs, Filipino with a cute face but not a crowd stopper. However, she has a body that I think is just perfect, in shape with great curves for such a small woman. Since we were just staying in, and it was the summer, she was wearing just a tank top and booty shorts. I know my roommate thought she was hot, and he had a thing for asian girls, even though his girlfriend was white. Since we were long distance at the time, Lauren usually wasn’t around, so it was a treat to have her living with me for a week, and my roommate certainly did not mind. She was always friendly with him, and playful, and she knew he thought she was hot, so she would try to act really sexy around him. He was a very nice guy, and had a girlfriend, which made him the perfect target for Lauren, because she knew she could flirt heavily and he wouldn’t do anything about it.

Hooking up (m)il(f) flight attendant (long)

I thought I would finally share one of my many stories after finding this subreddit.

I was flying back from a week long trip with my then girlfriend. We had visited some friends and it was overall a good trip. However, we had been fighting off and on. My ex was a very good looking girl. I knew it and she knew it. She was about 5’8″ slender with long black hair. She worked out constantly and was in great shape. Her best feature was her face. She was drop dead gorgeous. She had done some modeling off and on. She constantly got check out by guys. Now some of you will say if she was that hot what the fuck were you doing, as my title says, hooking up with a flight attendant. The only answer I have is that sometimes you just want something new and having been fighting with her the entire trip was no help. I know I know I’m a bastard for cheating…

Boarding the plane we were greeted by the flight attendants as normal. We took our seats and soon we were in the air. My ex opened a book and soon was dozing. I got up and went to the back of the plane to stretch. Being just over 6′, the seats on the plane were cramped.

I watched a gif of the Overly Attached Girlfriend and her sister being cute and I felt like expanding upon it…[FF]

Gif in question in the comments. Watch it before you read the story. Enjoy.

 

Another Universe: “just stay there!” said Laina giggling. “What are you gonna do?” spoke her smily sister. “just wait, I wanna surprise you”. Her eyes gently closed, Laina stared at her sister’s face. She inhaled the sight of the beautiful young woman her sister had grown into…She began to admire the freckles on her face, the way the darted and danced as her sweet lips widened. “You’re so beautiful” Laina spoke…

“What?! Just hurry up all ready!” giggled her sister. Her teeth were showing; perfect and dreamy. “oh..Oh yeah” she replied hazily.

Laina was just going for slight cute nose boop, but she here she was. Her best friend, her beautiful sister…she’d never loved anyone more. “I don’t know why I feel this way…if she knew how much I really love her, she’d be disgusted” Laina thought to herself.

Just then her sister clutched her arm. “Come on…I’m hungry. Let’s finish this”. Her sister’s touch so soft and warm, she studied her nimble fingers. She leaned in close to her sister’s face, so close she feels her exhale and examines her soft pale skin, scattered with adorable flecks.

Road Trip Stopover [M23, F24]

A few weeks ago I was informed by my father that his mother was recently diagnosed with lung cancer. She had not been feeling well the past few months and was going to the doctor when they finally figured out that she was sick. Luckily it had not spread to her lymph nodes yet, and they were able to get all of it out through surgery. This scare forced me to think about how I had not seen that side of my family in close to five years, largely because they had always been a few days drive from me, and it was difficult to get off work for long enough to make the visit worthwhile. Having gotten a new job that actually gives vacation time and located a bit closer to their part of the country than where I was, I figured that I would take a week or so to go up and see my grandparents, aunts and uncles, and cousins. As an added benefit, I would be driving through the city that my older sister, Laura, is in for the summer, allowing for a reunion as I had not seen her in almost a year. I had to work Friday night, so I figured that I would drive the ten hours to my sisters place on Saturday, spend through Monday with her, and then drive the remaining eight hours to my grandparents. I had already cleared the plan with everyone involved, and was looking forward to visiting family.

Kissing a Stranger Pt 3 [Ff][MF]

*This is where the story gets interesting. I hope you enjoy the direction it is going. As always, drop me a comment if you have suggestions or critiques. Thanks!*

The doors closed behind the pair of beautiful, naked women, and Ariella jumped as they slammed into the frame. The entrance hallway was lit by a candelabra that had been set on a decorative table just inside the door. Its tarnished golden arms and blood red candles did nothing to dissipate Ariella’s fears; if anything, it reaffirmed that she was in a dangerous place with possibly dangerous people.

The illumination gave away almost nothing of the mysterious house. Ariella could see that the furniture was elaborate, decorative, and useless in the way that no one was expected to use it for any other purpose but to show off wealth and impress guests. Ilara can consider me impressed, Ariella thought. There were large, framed paintings on the walls, but she couldn’t make out any details in such poor lighting. The hallway continued on in front of her to a grand staircase that rose to a walkway on the second floor. The light of the full moon shown through a grandiose window that rose from the middle landing to the ceiling, casting long shadows back at her. There were doors leading off of the hallway, but they were all closed. Ariella felt a flash of fear, the instinct to run was almost overwhelming.