I’m the world’s worst boyfriend (or at least I used to be), [mf]

This is my first post, and I have a lot of stories to tell. (all true). Some funny, some sexy, some lucky, and some strange. If you enjoy this at all, please let me know. And spoiler alert, monogamy is difficult for me. I probably need counseling, but you aren’t going to convince me to get it.

So the back ground story today, is me, dating a girl (A). She has her best friend (T). T is my ex girlfriend. We had dated a year earlier but never slept together. She broke up with me, I started dating A, end of story (almost). I worked with T’s mom, and T’s mom had a friend (R), whom also worked with us, and subsequently was the downstairs neighbor of T and her mom.
I was in High School, 18, senior year, and I had a perfect routine. Go to school, get out at 3, tool around for a bit, sleep with girlfriend at her house, then go to work for 5 hours, go home and then do it all again the next day. One day though, I see T in the halls at school and she asks me how me and A are doing. We talk for a couple of minutes and she tells me that she regrets breaking up with me, “mostly because we never got a chance to fuck.” Mr. non monogamous was developing on this sunny day, and I respond that I’d be happy to stop by anytime to fix that, but I make it clear that I’m not breaking up with A just to sleep with her. She says “stop by today after school”!

Like any prepared 18 year old, I have a costco supply of condoms in my car, so at 3 o’clock, (gotta be at work at 5), I tell A i’m going to be a little late, and I meet T at her apartment. If you remember though, R lives below T, and R is best friends with T’s mom. So I’m a little worried about getting caught, and i’m worried that T is going to tell A what a shady ass hole boyfriend I am. But after 5 seconds of exploring my morals, I arrive at T’s apartment, and walk up the stairs and gently knock on the door. (T’s mom is working btw), making this the perfect time to see her.

We don’t waste any time, door closes, making out, I carry her to her bed, and she tells me to go to her moms room (okay?), who cares what room, point being, I had my condom on and was sliding inside of her in less than 10 minutes of walking through the door.
So I pound it out, get up, flush my condom and wash my dick off, and she wants to go again. Spoiler alert, I had 2 condoms on me! (yay), I put on another and this time we have sex on the couch. I’m a little more winded now, as I sit naked on the couch, condom clinging to my sagging dick, full of cum, I reach down and pull the condom off and i’m holding it in my hand. She stands up and sits on my lap, reaches back and grabs my cock, and starts rubbing it, which felt great. I start getting hard again, and she tries to slide it inside her, but I stopped her. Simple explanation was, I didn’t want to get her pregnant, cause I knew she was crazy, and I wasn’t ready for all that. Unfortunately, this pisses her off and she tells me I can go. OKAY. Its almost 4 and I have to run to A’s house and fuck her before work anyhow. (highly motived 18 year old here, proud I was going to bang 2 girls in 1 day). Unfortunately T doesn’t let me wash my dick, she hurries me out the door, like I did her wrong.

I sneak back down the stairs and as i’m mid way down, R’s door opens (UH OH). R is about 40, and has huge titties. She is a little over weight, probably weights 180? At least DD’s, cut face, dark curly long hair. She opens the door and says “hello!, what are you up to?” And I say as quick as I can respond, “just dropping off some stuff for T.” By this time I have casually walked to her door as she was standing just outside of her apartment, under the stairs, talking to me. She says “it sure didn’t sound like you were just dropping off something, sounds like you were giving her something.” (apparently R’s ceiling was bouncing as I banged the shit out of T). My heart drops at this point in time, because I’m thinking that R will be telling T’s mom that her daughter was upstairs getting pounded by her fellow co worker.” Instead, R says, “i can keep this a secret if you can keep a secret too?” And in the best possible plot twist, she says, “come inside I want to show you something”

So I walk inside R’s apartment now and she asks me, “did you at least wear a condom?” and I was like, “fuck yes, of course” and she responds with a “good, I don’t trust her to not try to get pregnant.” R then states, “you don’t have to worry about that with me, my tubes are tied,” for which I say “let’s put that to the test.” Now at the time, I was thinking that we would schedule something, maybe come back the next day? or over the weekend? NO, R grabs me by the hand and leads me to her bedroom. I tried to stop her, being the courteous young man whore that I was, to let her know my cock was dirty, but R had my pants down and my cock in her mouth within seconds. She proceeded to suck my cock like I had never experienced before. I knew right away that older women were special and that girls my own age could be fun, but had a lot to learn. A few minutes later, we were in 69, and I was eating only the second pussy I have ever eaten, and R was sucking my cock so hard, she gave me a hickey on the tip. Not long after, I mounted her, pounded her for a solid 2 minutes, and had my 3rd orgasm in the last hour. I came inside her, got up, told her I was going to be late but I wanted to come back sometime soon. Pleasantries exchanged and I went to the bathroom to quickly soap and water my cock, so I can drive to A’s house (she was expecting me after all.

Its now about 430, I’ve got to be at work at 5. A’s parents get home about 5 from work, so I didn’t have much time. I honestly was too tired to fuck anymore, but A had soft skin, a pretty smile, and was laying on her bed when i got to her house. I let myself in like I always did, she comments on not thinking that I was going to stop by. We kissed a few minutes and Amazingly, I felt him coming back to life. A, was on the pill, and we never wore condoms. At the time I felt really bad about sliding inside her knowing I was risking her health, as I had just risked my own, but threw caution to the wind, and I fucked her harder than I had ever fucked her before. My stamina was strong and my dick was numb from the abuse it had just received. I finished with just enough time to get dressed and drive to the store.

One of the first people I see when I walk in, was T’s mom. She smiled and asked me how my day was. I simply told her, “so far pretty amazing”

Futures stories: Tell me if anything sounds good
-aol adventures including deaf girl (kind of funny)
-married lady in her driveway (I was used),
-college girlfriends roommate,
-married mom of 2 (I hope this wasn’t your wife)
-diabetic disadvantage (funny story)
-fucking girlfriends aunt

Source: reddit.com/r/gonewildstories/comments/7tpak9/im_the_worlds_worst_boyfriend_or_at_least_i_used