[M]y [F]irst sexual experience [MF]

**Disclaimer:** To anyone who is looking for a quick dirty story. Look elsewhere, this is a long story that is not nearly as raunchy as the majority of stories on this subreddit. I will attempt to provide a little background in my life so that you can understand why this moment was so important. I will mark where the “good”/sexual stuff starts but I believe the “good” stuff becomes “great” stuff with a little understanding of the characters. Also, I used to be a good writer but I have been out of practice since college, so this may be a little rough. Final note, I am a Male and this is written in my point of view. Now that that is out of the way let’s get started.

The story takes place like 10 years ago during summer after my graduation from High School.

*** BACKGROUNG ***

First, a little about me, because I know you are all dying to know who I am. At the time I was 6-foot-tall and kind of thin (155 lbs.). Okay I’m actually only 5’ 10” but 6 foot sounds better. I was in pretty good shape because I played sports year-round (soccer, tennis, and even captained my basketball team). I was also pretty smart; I took a total of 8 AP classes in high school and finished top 20 in my class with a GPA of 3.95. You may think, ‘this guy has it all. He is a sports stud and genius; he must get all the ladies.’ That is an incorrect assumption. I was a virgin through high school who had only kissed one girl.

I was the lone wolf that was everybody’s acquaintance but nobodies’ friend. I like to think of High School as synchronized swimming with your closest friends. Your score depends on how many friends you have and how synchronized they are. Some people may have like 15 people that are moving in a similar fashion but you can tell are not quite united. They will get a good score because of how many good friends they have. Other people may only have two or three great friends that are in perfect sync, they will also get a high score. My Swimming performance would be a disaster. I would have like 30 people swimming with me but we would all just be flailing to different songs, nobody on the same page as me.

At the time I didn’t see it as a problem because I was liked or tolerated by most people. Looking back at it now, I realize how much it hindered my High school experience. I didn’t have a “best friend” that I could trust no matter what. I didn’t have that one or two people that I could really be myself around. This was partially self-inflicted because I never really allowed myself to completely jump into a friendship. Instead of sticking with one group of friends, I would rotate groups of friends throughout the year. During the soccer season, I would hang out with soccer people. Once the season ended I would rotate to the basketball people until that season was over and so on. I didn’t have many classes with my teammates because I was in the AP classes. I was closest with the “smart” kids in my classes but I only saw them at school, I never had the time to hang out outside of school.

I was a Senior when I recognized this cycle but I didn’t think it was really a problem and it was too late to change anything. My life was fine, I wasn’t physically or mentally bullied, I wasn’t depressed, and I was getting good grades. I was generally happy but I think I needed someone close to share experiences with.

I had always wanted a girlfriend and I had tried multiply time to get close to someone but it just never happened. I think there are three different types of guys: guys who have a lots of friends that are girls but no “girlfriends”, guys who don’t have friends that are girls but can get a “girlfriend”, and guys that are in the middle. I do not have friends that are girls. I tried to be friends with girls but I guess it just always turned into flirting and not simple friendships. My theory is that I was not able to suppress my attraction for women. It is not as creepy as it sounds. I didn’t just run around the school getting boners all the time. It was just inexperience on my part. If I was just shooting the shit with a single girl and I was having fun then I would want to spend more time with this person. Since it is a girl, I would also notice that her eyes are beautiful. I may not have thought she was my type because she had short hair and a tattoo but after finding out more about her on a personal level I might find the look hot. Then I would think:

*I have fun when I am with her and she is pretty, I should try to make her my girlfriend.*

If I was more experienced with women then maybe I could have had plutonic friendships but, I was a high school boy who had lots of pent up sexual tension, so cut me a break. I now understand now that being nice to someone doesn’t always mean they want to bang them.

So here I am, this senior in high school that hasn’t been kissed or even had a girlfriend. I don’t have close friends that I can gossip about the subtleties of sex so everything I have learned about sex has come from *Paradise by the Dashboard Light* or movies. This is when Jess enters the story. I had never met her before but I knew of her. I had actually ranted to one of my teachers the year before because of the classes she was taking.

See Jess wanted to be valedictorian of the graduating class. I knew other people that wanted to be valedictorian. I did not agree with her methods because she would take easier classes and get an A+ while the people I knew would take the harder class and get an A. I had never had a class with her because I was working away in the harder classes while she was coasting through the easier classes. She knew she was playing the system but the school allowed her to do it until she was a senior. When she was forced into the more advanced classes, our paths finally crossed.

I’ll be honest, in high school, I was shallow. If you were a chubby girl I would not think you were hot. If you had weird teeth or acne I would not think you are pretty. That is not to say that I just ignored people I didn’t think were “hot”. Once I got to know you, I would soften but my first impression was very shallow. So, my first impression of Jess was “she’s hot.” I had never talked to her but all I could think was “hey she isn’t fat, I’d hit that.” The mind of a teenage boy, how despicable. I looked her up on facebook and found out our birthdays were 2 days apart. We had both turned 18 just before the school year started.

I will skip the cheesy conversations and text we sent but after like 3 weeks I worked up the courage to ask her out. And she said yes! It was facebook, so it was official! I had a girlfriend for the first time. It was great. We would text all night and all day. I learned that she loved the Beatles and hated Yoko Ono. She didn’t drink or do drugs which I didn’t either so that was good. I learned that her family were strict republicans but that she didn’t follow that. I learned that she was a feminist and Sandra Day O’Conner was her Idol. I also discovered she was very religious and didn’t believe in sex before marriage. I was not very religious but I can respect her beliefs.

I will gladly discuss religion with others because it is a topic, I am very well versed in. I had the same opinion of it then as I do now; You can believe anything you want but you cannot force it upon or negatively affect someone else.

After like 3 months I worked up the courage to kiss her. Yeah, I know it took a long time. I had actually tried 2 other times but when I zigged, she zagged and it just turned into awkward hugs. At 6 months we finally made out. I would describe it but I was very uneventful. It was some sloppy tongue kissing that was all mouth. I was just focusing on trying to kiss that I have no idea where my hands were. I think they were just down by my sides. I do remember that my dick was hard as a rock and if I didn’t have it tucked into my waistband she may have seen.

There are aspects of our relationship that I look back at and laugh. I remember that I once got hard when we hugged and she was so mad at me. She made me read a book about “the Devil’s Temptation”. I had to hide my boners from then on because there is no way I could stop myself from getting hard; I mean that’s what dicks are for. I also remember her asking me if I masturbated. I, of course, said “no, it is wrong.” I think she even believed me. Am I the asshole for lying or is she the asshole for judging people who do? I won’t lie, I felt bad every time I did beat it. I think she had trained me to dislike it so I didn’t do it much. But damn that first time I saw her in a bikini or the first time she changed in front of me (just down to her bra and panties). I probably could have burst right there. I think I spanked it like 2 times a day for like a week.

She wasn’t really that strict and I did enjoy the majority of the time with her. It is funny though; I remember so many of the bad times but only remember a couple of the good times. Its like going on vacation. If everything goes smoothly then you will forget the vacation but if your flight gets cancelled and you need to rent a crappy car, or the hotel room has mice and you have to move rooms in the middle of the night, it will stick with you. You will probably even look back and say you enjoyed the “bad” vacation because it was so funny. Our memories are so malleable.

I had learned and matured a lot during the relationship. In the “honeymoon” phase, I thought it was true love. I thought we would be together forever because I loved being with her. Then there would be some moments where I would snap back to reality. For example, we were watching some movie where Jessica Alba, Jenifer Aniston, or some other good-looking person (I can’t remember who) walked on screen with a bikini. I am sure they are wonderful people with great personalities, but if they are on screen with just a bikini on, I’m not too worried about their personalities. She asked me “Do you think they are hot?” This shouldn’t be such a loaded question because with like 90% of men and women the answer is yes. But I knew she wanted me to say, “I’d have to get to know them” or “Not compared to you” but there comes a time in a relationship where you must stand up for what you believe in. My time was then. I said “Yes, she is hot.” It is odd how telling the truth hurt her so much. There were a couple more moments like this were I realized that we saw the world differently, and you shouldn’t need to change to be with the one you love.

Anyway, so it has been 10 months and we would make out like once a week but it was getting antsy, because we couldn’t do more. After a weekend of thinking about it I decided I was going to break up with her. Now before I am called a terrible person because I am going to break up just because she wouldn’t put out, let me explain my reasons.

1. We were going to colleges that were 14 hours away. That is a long freaking drive.
2. Her parents were terrible. They were hardcore republicans and I dreaded seeing them.
3. She didn’t get Valedictorian (she got salutatorian) and I think she deep down blamed it on time spent with me.
4. She didn’t want sex of any kind and I was starting to need some sort of release. I was struggling to control myself. I didn’t want to force her to do anything she wasn’t ready for.

Okay so I have decided to end it but I was going to wait until after our senior trip to do it. I still wish I had someone close to me that I could have talked to about this. Should I have just told her right away that I wanted to break up or was I correct in waiting until after the senior trip? I guess I’ll never know.

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*** SEXUAL STUFF ***

Jess (my girlfriend) and I had planned a 4 day trip up to the beach with some of her friends after we graduated from High School. We had decided to wear our bathing suits in the car so we could go straight into the water when we got there, so I threw on my bathing suit and a white T-shirt and went to pick up Jess.

Jess had a mature beauty about her. Her face always reminded me of a distinguished lawyer that was independent and beautiful. Very pretty too look at but if you got on her bad side, you would regret it. She had dark black hair with bangs that ended above her dark brown eyes. Cute is not a word that would describe her face but it is a good adjective for her body. She was 5’5” ish maybe 115 lbs. with okay size A or B cups that always looked better because the bras were insanely padded. She had a flat stomach with a good-sized booty. She did well filling out jeans and yoga pants.

I pulled up to her house. She walked out of the house with a hoodie and sweatpants. Don’t get me wrong I love when ladies dress down to be comfortable but it is like 80 degrees outside so I didn’t understand the outfit.

I had to put up with her over-protective parents before finally escaping. When we get two blocks away, she takes off her hoodie and pants to reveal her actual outfit. She has on a white tank top that does little to hide the black strapless bikini top and some tight bootie shorts. She was looking amazing and showing off way more skin than usual. I realize why she was wearing the hoodie; her parents would never let her leave in what she is wearing. We drive over and pick up the rest of the people going with us.

Jess stays up front while her friends Brie and Kate sat in the back with Kate’s brother. I was driving a truck because we needed to haul some stuff in a trailer. It was a long drive (like 8 hours) and we left pretty early. It wasn’t long before everyone else in the car was asleep. It was just me and the road.

After a while jess woke up because she was not comfortable leaning against the window. The truck had a front bench seat so Jess decided to laying her head on my lap. In couple minutes she was asleep again. So, it was just me and the road, . . . and the boner that was growing. Her head was on my dick with just a thin pillow and my shorts dividing them. I couldn’t stop thinking about her just ripping my pants off and going to town on my cock. After like 10 minutes she shifted a little and moved her hand under the pillow onto my junk. It must have been by accident but it was the closest I had ever been to someone else grabbing my dick. It took a lot of willpower to resist gyrating my hips to get some friction going down there. She finally shifted so that her hand wasn’t touching my dick but during the adjustment the pillow shifted forward and her head turned toward me. She was still on the pillow but now she was breathing directly onto my crotch.

I mentioned in the background section that she didn’t like when I got boners around her so, I had become pretty good at hiding them. A lot of the time I would wear two pairs of boxers just to keep them more hidden. If I was wearing two pairs then I may not have felt the breathing on my cock. Heck if I was wearing one pair of boxers/briefs I may not have felt the breathing on my cock. At this moment, be it a blessing or a curse, I was not wearing any boxers. I was wearing my bathing suit because we were going to race to the water when we got to the beach. I wear bathing suits with the mesh so there was essentially one layer of cloth that was stopping the air blowing out of her mouth from contacting my dick. It is incredible erotic and exotic to feel someone blowing on your cock. The warm air was enveloping my cock. I didn’t want to move because it felt so good. Again, I imagined her just gobbling my cock down her throat. After like 1 minute I could feel the tinkling in my balls… I was going to cum. Some may say it impressive but I think it is more embarrassing that she was going to make me cum just by breathing. Well, I panicked a little because she was so close to it. There was maybe three inches between her mouth and my crotch. I was going to shift a little to move her head away but before I moved, I looked down and saw her body.

During the shifting the blanket that was covering her had fallen. She must have been cold because her nipples were about to cut through her top. She usually has so much padding on her bras is no way that her nipples could poke through but the bikini top couldn’t hold the nipples back. I also saw that the tank top was riding up and I could see her smooth white stomach. It was all too much and I could fell my dick pulsate but the thing that actually put me over the edge was a just below her stomach. I had never seen her in less than a bra and panties and I had only seen that a hand full of times. When I looked lower, I realized that the knot that held her bikini bottoms must have come untied. The booty shorts and bikini had ridden down and I saw a tiny patch of black curly hair. I felt her breath one more time and I busted in my pants. There was no holding back after seeing that.

I don’t have a pubic hair fetish. I have no problem against it but it doesn’t get me off by its self. It was the idea of seeing something that she was hiding from me. I was attracted to every centimeter of her and that was an extremely attractive centimeter.

It was not the best orgasm because I had to suppress it so much, but it was the first time I came without my hand. It was just some well placed clothing, or lack of clothing, and some hot air blown on my pants. I guess you could say it was my first blow job ?. I probably lost some readers (if anyone is still reading this) with that joke but I must push on because the best is yet to cum. ? (there go the rest of the readers).

So, I finished the drive. It was weird just sitting there with cum in my pants but I was able to cover it so nobody noticed. We finally get to the house and all run to the water. It is a fun time, swimming and sunbathing and just hanging out. Jess and I try not to be too “couple-y” because the others were all single and they would get uncomfortable. Jess and I would find a way to steal a kiss here or there; nothing too serious until the final night rolls around.

The house has a room with two beds, a room with one bed and a living room with a couch. We brought a blowup mattress so the girls take that into the bedroom with two beds. Kate’s brother takes the other bedroom so I get the couch that is in the living room. It’s a small comfortable couch but the location isn’t great. Everyone has to walk by it to get to the bathroom so I am constantly waking up because of the toilet flushing. I swear, they had to pee more times than 70-year-old with an enflamed prostate. I was constantly getting woken up and apologizes to.

It was the middle of the night and I hear someone go into the bathroom. It is the third and final night of this but I still get so annoyed. I just laid there fuming waiting for them to flush and leave so I can try to sleep again. After a minute, I heard the bathroom door open. Then I feel a body lay next to me. I assume it is Jess. It is a tiny couch so two people do not fit on it well. She must have been half off the couch because when I try to turn over to face her, I end up knock her off. As she was slipping, I desperately reached out and try to grab her. I get a handful of ass as I am able to catch her and pull her back. He booty is probably her best feature. It is large and fit. I always sneak peaks when she is in tight pants. I catch other guys looking too.

I had only ever grabbed her butt when she has jeans on. This is because she always seemed to be wearing jeans. While the booty is very nice, jeans do not do it justice. To truly understand how nice her butt is, you have to feel it without jeans on. She was not wearing jeans that night. I didn’t realize it at first because I didn’t know what I was grabbing. When I finally understood that she only had underwear on and that my hand was squeezing a cheek, I was shocked so I let go. This caused her to start to slide off again. Instinctually, I grabbed that ass again to keep her from falling. It was glorious. Her butt felt so much bigger without the jeans holding it back.

I said, “Your booty is a wonderland.” *I am so smooth. And I don’t even like John Mayer.*

She laughed and said, “thanks, but it is trying to pull me away from you. Let me try this.” She then pushed my shoulders and shifted so she was straddling me. My soldier was at attention instantly and there was no way I could hide it. She laid her head down on my chest, while my full erect cock was right below her glorious pussy. I was waring shorts and she was wearing panties but we both knew that they were essentially touching. I was completely stunned. This is by far the most sexual thing we have ever done. Minutes or hours may have passed; I had no sense of time. I had no idea what was going on, but I didn’t want to move because I didn’t want it to end. I felt her shiver. I wanted to pull the blanket up or hug her to keep her warm but I realized that my arms were pinned at my sides by her knees. I shifted my shoulder to free my arm and she shivered again then let out a gasp. I think she was holding her breathe because she started to breath really heavy. I still had no idea what was going on.

My right arm was almost free. I shifted up a little bit and she let out another gasp. With my arm free, I was able to pull the blanket over both of us. She lifted her head up and said, “It is too hot for that.” And shrugged it off. *But you are shivering*. She then leaned down and kissed me. We were not good kissers, but we were both young so we didn’t care. She had her tongue down my throat when she grabbed my hand. She guided it under her tank top and onto her bare breast.

I hope every guy is able to remember the first boob they touch because it is a very unique moment. I feel like there isn’t a way to truly explain it. To touch something that you dream about and realize that the action itself is not the best part. The best part is the reaction you elicit from the woman by just holding the boob or flicking the nipple. When I touched Jess’s boob, she let out the most glorious moan. She was still kissing me so she moaned into my mouth. I quickly freed my left arm and grabbed her other boob. It was an odd feeling because my arm had fallen asleep pinned at my side. I felt pins and needles as I softly caressed the breast and pinched the nipples. She had to bury her head in my neck to muffle the moans.

Then she slowly started to shift her hips up and back. I know she could fell every inch of my member because she would slide up to my tip and down to my balls. The friction pulling my pants down with each grind. In seconds the head of my dick was completely exposed as she slid back and forth. I could feel the beginning of an orgasm building in my balls. I could feel the warmth and wetness on my cock as he pussy slowly slid back and forth. I was still playing with her nipples when she stopped grinding and she started shaking. She was biting my neck really hard. I just held her boobs in my hands until she relaxed. I thought something was wrong so I asked, “Is everything okay?”

She took my hands, placed them on my chest then she stood up and said, “yeah I should go because I told Kate I was just going to the bathroom.” Then walked back to her room.

At the time I had no idea what had happened or even if the night was real. I suspect that she had had an orgasm and I will likely never know if she really did. She may have just been close then realized that it was a mistake or something. What I do know is that I had a raging monster half in my pants that needed to be tamed. So, I went to the bathroom and beat it. It only took me a couple seconds because I was so turned on. I actually had to beat it 2 more times that night before I could actually fall asleep.

** End of Sexual Stuff **

It is sad to say but our relationship was never the same after that night. She didn’t say more that two words to me the whole drive home. I tried to call her a couple times to talk about it but she didn’t want to. I felt terrible but I don’t know what I did wrong.

We finally met up to have dinner two weeks later. It wasn’t my intention to break up with her while she was clearly not okay with what had happened, but we started talking and determined it was the best option for both of us. We tried to remain friends but we found that we really didn’t have that many things in common. We slowly talked less and less until it had been like a week since I had heard from her. She seemed happy at school so I didn’t want to get in her way. It has been like 8 years since I have seen or heard from here. Maybe I should see how she is doing?

Thank you for reading this far. I haven’t told this full story to anyone before so it is nice to get it off my chest.

Source: reddit.com/r/gonewildstories/comments/dau7ah/my_first_sexual_experience_mf