Her first time squirting [MF]

She had been away at college on the other side of the country for about two months. We had talked on the phone or instant messenger basically every day while she was gone. One time, she even did a little strip tease for me on webcam and I sent her a few solo nudes of myself — not dick pics, full-on camera-timer posed photos — in return. We had an incredible sexual attraction to one another and it was great to know that, that was able to persist despite the 3k miles of distance.

For her birthday, her parents were flying her back to town for a long weekend. We made plans to see one another as much as we could during that time — Friday night, Saturday night, Sunday night. This is the story of Friday night; her Birthday. We were going to go swing dancing like we had on our first date a few months prior. She had dinner plans with her family and I had an obligation to attend to so the timing worked out that we would simply head to the dance a little late and probably end a little early so we could have some fun. As the expression goes, the best way to hear god laugh is to announce your plans, so things fell apart pretty quickly. She showed up to me on time, but my event ran over by about an hour. I remember seeing her show up in the lobby and I wanted to stop what I was doing and run out to see her, pick her up, and run away with her, but some foolish duty compelled me to persist.

My first Asian girl. Her first time ever. Memorable for both of us [MF]

We started talking online at the beginning of March. She lived in the same state but a few hours drive away. She only had one photo on her profile and claimed she didn’t have anymore to send. That said, the one photo was really cute. She was Korean, beautiful smile, long dark hair, and a great figure. She was whip-smart, really sarcastic, and kinda mean. She was the kind of girl that knew what she wanted and didn’t take shit from anyone and I really liked that about her. We never really talked about dating or sex and there wasn’t a lot of umph behind our conversation so we didn’t put out the effort to meet. That was, until the end of that summer; toward the end of August she sent me an e-mail that read “This is um random but, do you want to meet this week?”

We had some back and forth for the next day or two trying to hash out the details. She wanted me to come to her — in the middle of nowhere — on a Thursday and stay the night at her parents place. I thought that sounded like a plan that offered nothing for me, but she eventually let me know that her parents would be out of town Thursday – Saturday and… she had the house all to herself.

Her mom was 10 feet away doing chores while I fucked her in the living room [MF]

I had met her the day before and we had just had one of the most wild and exciting sexual encounters of my life. I had spent the entire day thinking about all of the details of the night before and could not get it — or her — out of my mind. I called her and asked if she wanted to see me again that night and she was excited. I don’t think either of us had any idea that we were going to connect so strongly, but we weren’t going to miss out it. She was due to move away in about two weeks, head off to college across the country, and I wanted to get as much time in as I could while she was still here.

I got to her house around 7 pm and strode boldly to the front door to say hello. Her mother answered, a very handsome woman with a genuine smile, and asked who I was and what I needed. I told her I was there to see her daughter for our date, and I was caught off guard at the look of surprise on her face. Suddenly her daughter, lets call her Rebekah, popped around the corner and tried to shoo her mom away. I guess she hadn’t mentioned that she was going anywhere that night.

She fucked me so good on the side of the road that I think I fell in love [MF]

I had been messaging people online on HotOrNot-dot-com for a few months and it had been going pretty well. Unfortunately, most of the people I was matching and connecting with lived in really random places. A few in New York, some in California, some in Europe, some in Washington D.C., Texas, etc. Not really conducive for dating, a relationship, or just hooking up. Interestingly, I did make a few good friends through that site who are still in my life to this day — but that isn’t here nor there. Today I’ll tell a story about the sex that ruined my love life for years in the best way possible.

Her photo on HotOrNot was absurd. She was clearly making a joke about the whole experience and not trying to get rated highly, but it caught my attention for sure. In the photo she was standing next to a mailbox — spray painted green and black — wearing a trucker hat with a “fuck off” look plastered all over her face. She was wearing some kind of casual wear — maybe tennis gear? — and the only other thing that was obvious was that she had bright red hair and a pretty face (despite that she was mean-muggin’ it).

The first girl I met online turned out to be a nympho. [MF]

Despite how many of the stories I tell — or many of the things I do in real life — portray me as cocky, bold, or extroverted I am, in fact, deeply shy. At some point along life’s path I realized that my ambitions were greater than my nature would allow; so I had to pretend to be confident and affable even when I knew it wasn’t really the truth.

This story takes place while I was still learning that lesson and was getting my feet wet with figuring out how to meet people. I had stumbled happily into two relationships prior to that point and learned a lot, but the introductions to those people had been flukes and I didn’t know how to replicate that. Luckily, the Internet was brimming with opportunities at that time and MySpace had just come out and HotOrNot-dot-com was a thing.

She told me to ‘kiss her ass’ and I did… [MF]

I studied several martial arts for a long time at a few different schools all across the country. One style that I really got into had a semi-annual gathering which was a lot of fun. People would kick each others asses, train, learn, share stories, eat good food, and — more often than not — hook-up afterward. The first time I went I wasn’t sure what to expect; as far as I knew the people I trained with were as wholesome as they pretended to be in front of the students. Little did I know…

The first few hours of the day after landing and grabbing lunch were pretty standard. Lunch was good for me, I had a massive confidence boost right out the gate. When we walked into the restaurant the hostess looked at me and said something to the effect of “Are you allowed to be here?” I was surprised and asked “Yeah, why?” She looked me up and down and said “You are hot as hell, if you were my boyfriend I wouldn’t let you leave the house.” No one had ever said anything so direct and bold to me in my entire life and it was amazing. After that we checked in to the hotel, checked out the locale, talked about how awesome the weekend was going to be and discussed what to do next. Our group probably had eight to ten people. Half were instructors and the other half of us were students. I was relatively new, I had maybe trained there for six months at that time.

She called me “Daddy” while we fucked on her parents bed. [MF]

It was her graduation day. Everyone was in a tizzy getting ready to go to the college before a long day of waiting around for one name to be said so we could cheer our lungs out for 15 seconds. The events started early, her family was there, most of her friends had gone to the same school and were graduating with her. Afterward a big group of us were supposed to meet at a very expensive restaurant half-way between the school and her parents house for a late-lunch/early-dinner. She wanted to go home first, however, and change out of her robes and into something nice. I volunteered to drive her so her parents could head right to the restaurant and get things set up with balloons and other decorations. She had gotten her hair cut for the ceremony and it looked really cute. I loved her with long hair, but this new bob was fantastic and she loved it; anything that made her smile was a good thing. I remarked about how much I loved it on the way back to her house after the ceremony and told her it would go great with the outfit that I had just bought for her.

Dorm Room Video [MF]

My girlfriend and I had been talking about trying out some new kinky things recently. We were young and really exploring what we were interested in sexually. I had only been with one person before her and she had only been with a few people before me; almost all of our interactions with other people had been vanilla. With each other, though, we had found someone to experiment with.

Her dorm-mate was going home for the weekend and we wanted to capitalize on the opportunity for some privacy so we agreed to a weekend-long fuck fest. She and I had been experimenting with photos for a while and I had tried to make a video with my prior partner once — very unsuccessfully — and had taken a very awkward solo video of myself once as well. That said, I wasn’t ready to give up on this fantasy; so I “borrowed” my parents camcorder and stand, took a blank tape, and packed them up for the weekend. I made a pit stop at the erotic boutique near the liquor store which I had seen many times on my way to go visit my girlfriend, and I picked up a vibrator, some lube, and a DVD porno at random — thinking they were all likely the same. They are not. Please be aware right now, all DVD pornos you find in a strange porn store are not, I repeat NOT, the same.

Parking Garage – Almost Caught [MF]

We had gone to the movies at the theater near her college. Despite the fact that the movie had absolutely nothing sexual in it we decided to get handsy in the back row. Well, technically, not the back row, but no one else was behind us… that we noticed. She wore a short skirt and no panties and it was just too tempting not to slip a finger insider her. For the greater part of thirty minutes I just played with her, teased her, and worked her up. Never went too fast or pushed too far to accidentally rouse anyones attention; just a little playful fun for the college kids on a Wednesday night.

When the movie was over we were in dire straights and needed to fuck. We went back to her dorm room hoping to sneak in some playful naked time, but her roommate was there and she was aggressively disinterested in leaving. My girlfriend and her roommate had a chat while I waited out in the hall — I think there was some negotiating going on in the attempt to trade some future favor for a night alone with me. No luck. The roommate was offended at the idea of anyone having sex in the dorm room at any time for any reason. My girlfriend did not inform her that we had been having sex in their occasionally for the past few months when she was in class. The bottom line was — according to the roommate — that it was gross to think of a man being naked in their dorm room and it was not okay to even ask.

Another Photo Shoot [MF]

Link to Part 1 in the comments…

We had been dating for a few months and it was incredibly fun. Here I was, under-employed (I was working in a machine shop totally unsure of what I should be doing with my life), 6’2”, 200 lbs, dark hair, green eyes, athletic build, socially awkward (because it is hard to shake being a long-time D&D playing, video gaming, swing dancing, comic book loving nerd). She was beautiful, finishing her last year of under-grad, 5’4”, 100 lbs, chestnut haired, blue eyed, actress and part-time model with a thick ass, full lips, and an insatiable libido. I felt like I was the luckiest man alive. I had met her through a mutual friend a few months earlier — he had a huge crush on her, but he also had a girlfriend… — and we had been dating ever since. In thinking back on that relationship, we didn’t have very much in common, we both just loved to fuck and couldn’t keep our hands off each other.