My First Time Cheating [MFF]

This story happened when I was 19 years old.

At this point in my life I was bartending and going to college in my home town with plans to move 9 hours away to finish my program. I had just gotten out of a long term relationship with a girl I was not over. All of my close friends moved away to college already, so I had no one to really talk to at this point. I spent a lot of time with work friends.

It was a point in my life where alcohol and drugs were a daily occurrence and my job didn’t help. My pot dealer was the other bartender, and my drinking buddies were co-workers. Not a healthy point for me, that’s for certain.

One evening I was on one of the few days off. I was at home a few hours away from going back to where I work to meet friends for drinks. While I was waiting, I went on a local ICQ group for singles. I was trying really hard for the rebound since I hit a dry spell for a couple of months after breaking up and needed something to help me bounce back. I figured meaningless sex would do that.

While on ICQ, this user PM’s me. She keeps talking about knowing me, but keeps her info vague and won’t send a picture. Still, she insists we know each other. This went on for about an hour. Our messages became very flirty. Finally, I told her I was going to “Billy’s Bar”, the only local nightclub. This was the plan after a few free drinks at the place I work.

This unknown person says “I’ll be there and if you find me I will buy you a drink”. I ask “what if I don’t find you?”. She says “Well, your loss”. Cocky but intriguing.

After some pre-drinking with my co-workers we made our way to Billy’s Bar. Once inside, we did rounds. Rounds were basically just walking around the bar looking for people we knew, or people we want to know. Pretty much solely women. It never worked, but we didn’t know that at the time. Hopeful youth I guess.

After several rounds and not finding anyone I recognized, I kind of gave up. I had a feeling she was messing with me and creating a wild goose chase that I would never solve. I gave up for the most part. I mean I kept my eyes open, but wasn’t actively looking around.

Some of my co-workers grabbed me to go do shots. As we got to the bar, there was a small line in front of us. We stood there waiting, then I noticed someone I recognized. It was a girl named Mirna.

Mirna was this beautiful eastern European girl who was best friends with an old ex of mine. To be honest, Mirna was the reason that ex and I stayed together for as long as we did. I wanted to be around Mirna, and that ex was how I did that. At least until she figured it out and stopped inviting Mirna. We broke up shortly after that.

In the couple of years since then I had run into Mirna a couple of times. Mostly from a distance or in passing. I wanted to say something, but never did. Well, I figured this was the night I wouldn’t be afraid. Liquid courage helped with that.

Mirna got her drinks and turned around. She had two, so in my drunken stupor I said “Are you double fisting it, or are one of those for your boyfriend?”. She laughed and said “Nah, just some loser”, then hands me the drink. I was confused and not really sure why she gave me a drink, or who this loser was. No idea she was making fun of me.

I ask her what the drink is for, and after some sarcastic mocking she says that she promised that if I found her she would get me one. At this point I completely forgot about that. I just figured Mirna is fucking hot and I wasn’t letting my newly found courage go to waste. It was totally shocking and unexpected that she was the same person I was speaking to early that day on ICQ, but here she was.

We spent the rest of the night tucked away into a dark corner of Billy’s Bar talking. She was actually drinking water, so I switched it up as well. She drove me home that night and we made plans to hang out that weekend. We kissed goodbye and left.

That week leading up to the date we chatted on ICQ for at least an hour a day. Both of us were quite cocky and I think that is one of those things that drew us closer.

Finally the weekend came. I had a plan to take her to the local lake and cook her dinner over the fire and polish a bottle of wine. Instead she calls me a few minutes before and says she has to cancel. Fuck, I knew this was too good to be true. My ex (her friend) and I didn’t exactly end on good terms. That was when I learned honesty isn’t always the best policy. I said some poorly chosen words when I was breaking up with her. I took some shit from her friends for it, but nothing I couldn’t handle. I figured this was a long thought out plan to fuck with me.

I didn’t hear from Mirna for a few days and figured that was it. I went back to my old ways of heavy drinking, eat sleep, repeat. Then nearly a week later Mirna writes me again. She asked if I was mad at her. To be honest, I was disappointed because I had my hopes up, but I wasn’t mad. I didn’t care enough yet to be mad. She said something came up but she couldn’t tell me. Whatever, I had already come to terms with this not working.

Then Mirna asked me to do a make-up date the next night. She said she would plan it. I agreed, but wasn’t holding my breath. Good thing because the next day she cancelled again. I gave up all hope for her at this point.

Then just as I was about to go to sleep, she wrote me again. This time it was a simple “Are you awake?”. “Yes” I responded. “Can we meet right now?” she asked. “Sure, come to my place” I said. “Be there in 20” she replied.

I honestly wasn’t expected her to show. I figured if she bailed this time I was just going to block her on ICQ and not deal with her again.

Surprisingly, 20 minutes later she arrived. I invited her in and made her a drink. She refused and asked for a water. She then sat down and told me she wants to tell me something but is very afraid of how I will react. I had no idea how to react so I just told her “well let’s hear it and we’ll see how I react”.

She tells me that the reason she has had to cancel on my twice is because she has a baby. That also explains why she is sticking to water. The first cancellation was because the childs father forgot it was his weekend and took off out of town. The second cancellation was because the child got sick.

My immediate thought was “FUCK!!!!!!!!” I knew this was too good to be true. This physically perfect woman who has an amazing and fun personality has a kid. Of fucking course she does.

I put on a calm face and told her that I am shocked she has a kid. I told her that I don’t know the first thing about kids and that I didn’t know how to respond to this. Then I asked her how she wanted me to respond. She just said, “well I was hoping we could still give it a go”.

I wasn’t really looking for a serious relationship. I wanted a fling. Still, I agreed to go on that date. We set a date/time and made it happen.

She planned this date. It was simple, a picnic in the park followed by a walk along the river. We ended up at my place afterwards. There was making out, but nothing more. It was a great night.

We had several more romantic dates, each one getting better and better. We never had a dull moment or a point where we didn’t know what to say. After the 6th date Mirna asks me what I want from her and this relationship.

I knew this was coming so I was prepared, or at least thought I was. I told Mirna that I wanted to have fun while I am here, but would be moving 9 hours away in a couple of months. I didn’t want to complicate things by getting too serious. I knew Mirna was upset by this, but I couldn’t lead her on. Mirna reluctantly agreed that we would keep this casual.

At this point I still hadn’t made it to second base. Mirna was a good bit shy about her body after having a baby. I understood that and didn’t pressure her.

A few nights after this talk about remaining casual, I was at work. Mirna and a big group of her friends came in and sat nearby. I stopped over and said “hi”, then went back to my job. I could feel them staring at me a lot. I recognized a few of them from when I was with my ex. It was a little uncomfortable, but as they were leaving Mirna stopped by and said “my friends approve so I have a surprise for you tonight”.

After work Mirna was waiting for me at my place. I was interested in this surprise, so I immediately asked her. She pulled out a condom and a note. I read the note first, and it said;

*”I’m too embarrassed to say this so I wrote it down. I’ve only had sex three times. Once with my first boyfriend and I didn’t want it but he forced me. Then two times with the father of my child. I have never had foreplay of any kind and am too shy for that.”*

I was a little confused. I told her that if I ever make her uncomfortable, to let me know. We went downstairs and after that note I wasn’t sure if I should try, even though she did hand me a condom.

We laid on the couch watching a movie. We had a heavy fleece blanket over us and were down to shorts and t-shirts. I was spooning her and had my arms around her. She smelled like strawberries. We slowly rubbed our bodies together while in this position. Finally, she rolled over and faced me.

I asked her if she was okay. She said she was scared. This is the first time she was naked around anyone since having her baby. She was very insecure about her body. Honestly, I was a little afraid of what I was going to find. Her fear just got me on edge.

I decided to take off her shirt. She had on a thick bra which she said was to ensure milk doesn’t leak through her shirt. Oh fuck, I forgot about that. Now I am afraid to play with her tits. I moved on to her shorts. I reached down them to begin fingering her. She stopped me. I could see that she was worried about what I would think.

Instead I started kissing her. We were in a full on make out session. My hands were rubbing her ass and her tits. I would occasionally rub her shorts as well. Then I told her to trust me. I said that if this makes her feel uncomfortable to say so immediately.

I pulled her shorts down exposing her freshly shaven pussy. I guess she knew she was getting action, if the condom didn’t already give that away.

I then pulled down my shorts exposing my erection. I made her lift her top leg and I put my cock against her pussy. She put her leg down again pinning my cock between the tiny gap she had. We dry humped like that for several minutes. I used my hand to push my cock more firmly against her pussy as I ran it back and forth.

After minutes of that I could feel the friction almost totally go away. She was wet. I mean really wet. I rolled over on top of her and knelt between her legs. I leaned in for a kiss and slowly worked the tip around her pussy. She was loving it. She was breathing heavy and getting wetter.

Finally I pushed my cock inside of her. I went in deep and immediately was caught off guard with how tight her pussy was. She just had a child for fuck sakes. I had to say it, “wow, you’re very tight”. She smiled and said she asked the doctor for an extra stitch. Apparently that’s a thing.

I fucked her slowly. I could feel every part of her pussy gripping my cock. It only took about 10 minutes of that before Mirna started shaking. It was right at that point that I remembered the condom. I put it on once she finished because I knew I was close as well. I went back inside of her and finished almost immediately.

In the next few weeks we regularly discussed our status and I was adamant about keeping it casual because I was leaving. I didn’t want to do long distance. I also came to realize that Mirna was looking a lot more long term than that. I guess having kids will do that to you.

Over the next couple of weeks I realized that I needed to distance myself from Mirna. I figured it would help both of us ease into the end once I moved away.

That was when I met this cute little blond. My only sober hobby at this point was mountain biking. One of the waitresses at work was telling me she had a friend who just got a new bike and wanted to show me. We agreed to go for a ride that evening. Me, the co-worker, and her friend Kim.

We decided to meet at a trail in the middle of where Kim and I lived. My co-worker bailed last second but pushed for Kim and I to still go. We had a great ride that day lasting over 4 hours. At the end of the ride we ended up at a small pond. We were sweaty and covered in mud, so I decided to jump in for a dip. I stripped down naked and ran in. Kim stood there on her bike in shock that I would do that. I pressured her into joining me. She said she would, but not naked.

She pulled off her shirt and shorts and was left standing in her bra and panties. She came into the water and we splashed each other a bit. Then I told her that she should get naked. I’m pretty sure I made chicken noises even. She gave in. She took off her bra and panties.

The water wasn’t exactly crystal clear. It was a mud bottom, so every step made the water that much cloudier. Still, her breasts were exposed. She had very round breasts with perfect little nipples. They were very perky, but she was very fit so it made sense. After meeting her milf of a mother, it made even more sense.

She came over to me and I said I don’t believe you are naked. She grabbed my hand and put it under the water and onto her pussy. Yup, there was more uncertainty. She was definitely naked. I had a bit of an erection at the time because her tits were nice and I was 19 years old. It happens.

Kim was standing really close and then it touched her. She gave me an odd look as if to say “is that what I think it is”. I am sure I went red blushing. Then she reached out and grabbed it. I pulled her in closer and she wrapped her legs around me. We made out in the water in what was now moonlight. Before we went too far, we stopped and went home. We both showered and decided to meet for drinks once we were clean.

My friends were having a party that night. It was perfect. Kim came over and her and I spent the entire night in the backyard of this party at the fire pit. We complained about how sore we were from biking. Then we decided to give each other massages. The backyard was empty. Most people were inside doing beer bongs or downstairs testing the gas mask bong we made that summer.

After several hours of isolating ourselves from the party, we walked back to my house which was only a couple of blocks away. Once we got there, we laid on the floor and turned on a movie. The movie was just background noise because we started making out almost immediately.

I remember thinking that Kim was cute on our bike ride, but when Kim put some effort in, she was a bombshell. We got hot and heavy quickly. I pulled her pants off exposing her white panties with a small blow bow on the top. I kissed her all over as I took them off.

Once they were off, I kissed her thin blond mount. I worked my way down to her clit where I slowly licked it. Moving my tongue in circles around it while using a finger to lightly graze her vaginal opening.

It wasn’t long before Kim stopped me and said she was close. I told her that’s fine, you can cum as many times as you want. She laughed and said that after she finishes, she gets too sensitive to continue. She pushed me onto my back and pulled my pants off. She grabbed my cock and said “it feels bigger than it did at the pond”… DAMN COLD WATER!!!

She began licking the tip. Then sucking the tip. She was using a little more of her teeth than I like so I had to stop her. I just told her the tip is extra sensitive. So she went deeper. She was very robotic like, but it was still a blow job and even a bad one still feels good usually.

After sucking on my cock for a few minutes she climbs up on top of me. She slowly moves the tip of my cock back and forth on her pussy. Then she put in the tip. It went in with ease because she was so wet. She went a little further. Fuck, she is tight as well. She kept going down, inch by inch by inch until she was all the way on.

She leaned up, stuck her chest out and slowly grinded back and forth. Every thrust felt like my cock was hitting her ovaries. It felt like my cock was too big for her tiny little pussy. Her thrusts got faster and faster, then all of a sudden she began moaning. Her orgasm felt like it lasted for minutes. Once she was done, she asked if I could go doggystyle because her clit is too sensitive.

She rolled over onto all fours. Her ass was firm and round. It was as pale as the rest of her skin. I could see her pussy was red from grinding me so hard, no wonder she was sensitive. I admired the view for a second before moving over to her. Her back was arched and her pussy was open. I grabbed my cock and slid it inside of her. Once I was in I noticed that her labia was gripping my cock. Every time I pulled out, her skin would pull out as well. It looked like I was about to tear her it was so tight around my cock.

I slowly fucked her for a few minutes before she put her shoulders on the floor. She leaned to the side and looked back while her shoulders were down. It was hot. I had never made eye contact with a girl I was fucking from behind. She made these hot faces that were a combination of joy and pain.

I finished quickly once she began looking at me. I came inside of her after she told me she was on the pill and it was okay.

After we finished, Kim rolls over and looks at me. She says “what’s going on with you and Mirna?”. FUCK!!!!

I told her the truth. I said we were casually dating but weren’t exclusive. I told her that I like Mirna, but I am leaving for another city in a couple of weeks. It turns out Kim was heading to the same city and to the same college. I immediately saw the potential here. Kim was okay with that explanation.

Even though Kim and I were starting something, I never did stop seeing Mirna. She was kind of my dream girl and we got very close for those last couple of weeks. Then a few days before leaving I made the tough call and told Mirna that I care for her but don’t want to continue this any further. I figured it was unfair to her for multiple reasons. Kim being one of them. She still didn’t know about Kim. Mirna was heartbroken, but that’s how it had to be.

A week later I packed up my car and drove 9 hours to my new home. The first night I met up with Kim who helped me unpack the few boxes I took with me. Mostly just CD’s and computer stuff.

Kim and I had spent almost every day of the first month together. I was speaking to Mirna on ICQ regularly. She was struggling with the distance, but it seemed to be getting better.

I really liked Kim. I especially liked fucking Kim. The problem was that Kim felt a lot more like a good friend then a girlfriend. We had a talk about that and decided that we weren’t relationship material. We decided to be friends with benefits instead. We still hung out like a couple, but there was never any commitment or exclusivity.

Then around the one mark of being in this new city Mirna shows up out of the blue. It happened to be my birthday so she showed up to surprise me. Her surprise was her laying in my bed with lingerie on. Now this was probably one of the sexiest surprises I had ever had, but that could have been very very bad. Fortunately my roommate was on guard and making sure to stop me if Kim was with me. She wasn’t.

Mirna and I made love. She gave me head for the first time and let me go down on her. It was awkward and fumbling since it was her first time, but it showed that she was comfortable with me. We stayed up all night playing with each others bodies.

The next morning Mirna tells me that she can’t not have me in her life. I realized that despite Kim being an amazing person and an incredible lay, my mind was always on Mirna. I missed her.

We spent the entire next day talking about things. We decided that we would give long distance a try. For the first time we became exclusive. Mirna was going back to school the coming semester and was accepted in a school that was only 2 hours away. That made our commutes much better.

The week after committing to Mirna I had a night planned to meet up with Kim. We were friends at this time, but still boning, so that was pretty much the point of the meet-up, at least to me. This time it was different though. I was going there to tell her we need to stop having sex.

Good intentions aside, we fucked like animals after I told her Mirna and I were back together. It felt like Kim was jealous and wanted me to realize what I was missing out on if I stayed with Mirna.

In hindsight now that I am older and wiser, I was thinking with my dick and nothing else. That being said, I couldn’t stop thinking about Kim and how incredible of a lay she was. I basically split my weeks between Kim on weekdays and Mirna on weekends. Kim knew about Mirna, but Mirna only new Kim and I were friends.

This went on for 7 months until the next summer break. We all returned home to work. I went back to my job bartending and Kim started at the same place waitressing. Mirna and Kim started getting close as friends.

It took about two months, but Mirna called me crying. I rushed over to see her, and she told me that Kim told her I was cheating on her. I was silent. I was busted.

Mirna asks me “who is it”. WHAT??? Kim told her I was cheating, but didn’t explain that it was her I was cheating with. That’s kind of fucked.

I decided to tell Mirna it was someone she didn’t know. I said I was so sorry and that I wouldn’t do it again. Lots of words were said that I’m not proud of, but in the end she decided to give me another chance. Unfortunately my affair with Kim had done too much damage. Mirna and I broke up for good. I stopped speaking to Kim at that point. I blamed her when I now know it was all my fault. Immature and selfish youth.

The thing about all of this was that my ex before Mirna and I broke up because she cheated on me. That was a long term relationship and I know how much it destroyed me. I have never regretted anything in my life as much as hurting her that way. She didn’t deserve that. I didn’t deserve her.

We didn’t speak for years. Then one day out of the blue she writes me on Facebook. Apparently she got married to the father of her child shortly after we broke up. She wanted a father for her kid and who better than the actual father. He was a loser who was beneath her, but I think I crushed her self-esteem.

Well the day she wrote me was the day she signed the divorce papers. She had another kid that looked to be about the same age as I would have been in the picture. She confirmed that I was not the father. She said she was pissed at me and had sex with her ex, the father of her child, and got pregnant. She said that was the entire basis of their marriage until they realized it was stupid.

At this point I was with another girlfriend who I was serious about. I still had to see if those feelings remained so I decided to meet her. We went to a local park and had a picnic. Honestly it just felt right to be near her. She still smelled like strawberries, and she still had the perfect face. We kissed for a second, I had to see. I’m glad I did. The kiss felt flat and wrong. I knew at that moment that my current girlfriend was who I wanted. I hated that I had to try, but I needed to prove to myself. For those years I had the feeling that I missed the love of my life. I didn’t realize that I was currently with her.

I’ve made amends with Mirna. She knows I will always love her and be there for her, but we will never be a couple. We parted ways once again and now our relationship is a yearly catchup through Facebook.

Kim and I remained friends after all of these years. She really was a good buddy. I would be lying if I said the thought of sex with her didn’t cross my mind anymore. But I can control myself now. Much better than back then.

Source: reddit.com/r/gonewildstories/comments/5mitox/my_first_time_cheating_mff