I am a 53 years old [M], single now. When i was a 22 years old, I was single and just looking to hookup. I had a girlfriend in high school and got laid daily. After she broke up with me and ran off with an older dude, i kind of went of the rails and started juggling a few different girls leading up to this infamous night.
Colleen was my FWB hookup. She was about my age. We would get together every Thursday because her mom worked late. I lived on the north shore of Long Island and she lived way east, about 45 minutes to an hour away. Her mom worked near where i lived. I would get home from work, take a shower and head out to her house. Colleen was a redhead, blue eyes, medium build, big tits and LOVED giving head.
One night i got home from work around 5pm. I got the usual call from Colleen asking if i was coming over. I jumped in the shower and headed out east to her house. We really didn’t waste to much time once i got there and we would go at it for an hour or so, ending with me finishing in her mouth, which she loved. Her mom would usually call before she left work to let her know she was leaving. A few times, i was pulling out of the driveway as she was pulling in. Her mom liked me, so it wasn’t a big deal.
I got in my car and headed home. It was probably about 9pm when i left. My plan was to go home, take a shower and head out to this bar to meet up with friends. After showering, i was heading to the bar and remembered it was bowling night and Girl#2 was at the local bowling alley.
Kathy was this girl who worked at my job in the Accounting department. She was the biggest cock tease i have ever met, but for some reason i put up with her shit because i wanted to fuck her. She wasn’t that great looking, but what a body, what an ass on her. She was about 5’2, slim and petite, kind of flat-chested. I had tried for awhile to get in this chicks pants, but she would just come up with excuse after excuse. I would go to the bowling alley and wait in the bar for her, but she would finish bowling and walk her bowling partner to his car, wink, wink. I found out she was banging this married guy, but wasn’t getting anything from her. We made out a few times, but nothing further than that. I headed to the alley and she was just finishing. I asked her if she wanted to hangout, get a drink. Again, got the usual excuse about having to get home, etc. I basically made up my mind to forget about her. I told her i was leaving and she asked if i was mad. I was pissed, but said i wasn’t. She sensed that i was frustrated with her cock teasing and asked if i would drive her to her car that was in the back of the parking lot. I drove her to her car and waited for her to get out, but she sat there asking me over and over if i was mad. I insisted i wasn’t and she said can we get together maybe on the weekend. I said, yeah, whatever’, knowing it was bullshit. So she looks at me real hard for a second and then pulls me in for a passionate kiss, with her had on my crotch. I ended up getting a pity BJ from her. It was just to keep me interested. It was an alright BJ. I never did get to bang her.
After the car BJ, i headed over to the bar to meet my friends that worked at the country club i worked at on the weekends. Here i encountered Girl#3.
Kimberly was another girl from work. She was two years younger than me. We worked in the same department and had hung out a few times after work. She was kind of a lush and got hammered after two beers. I would turn around and she would be making out with some random dude. I would always give her a ride home from the bar because she didn’t drive. A few times she put the moves on me, but couldn’t bring myself to do it.
So, i walk into the bar around 11pm and see Kimberly at the bar with some random dude, drunk off her ass. Kimberly was cute, strawberry blonde, about 5’5, medium build, A-cups, if that. She sees me and immediately staggers over to me. The guy seemed relieved and made his exit as i was talking to her. The bartender told me he cut her off awhile ago. I knew all of the bartenders because i hung out there so often. I paid her tab and told her i would take her home. I get to her house she shared with her mom and she tells me her mom is away for the weekend. Now, i can’t let her walk up a flight of stairs and into her apartment as inebriated as she was, so i walk her up. She tells me to have a seat in the living room while she goes to the bathroom. After about 5 minutes i hear these noises coming from the bathroom and i immediately thought she was throwing up. I walk through the bedroom and knock on the door and she says come in. I walk in and she has her shirt half way over her head and she is in just a bra. So i get her shirt off for her and she takes off her bra and her tits didn’t look that bad despite being small. She had nice long nipples. I kept telling myself, don’t do it! But the little head won over again. She brushed her teeth and changed into a t-shirt and panties and got into bed. I made sure that she had a glass of water and a bucket next to the bed just in case. I told her i would talk to her tomorrow and she said can you stay until she falls asleep, i said OK. She insisted i take my shoes off and lie down on the bed with her. Oh boy, here we go. I lie down on the bed with her and we are just cuddling, i was rubbing her shoulder waiting for her to fall asleep. Her hand went from my chest to my stomach to my crotch and there was no turning back. As drunk as she was, she was down for anything. Luckily i had a condom in my pocket from Girl#1. No BJ from Kimberly, but several positions, doggy, cowgirl, etc. Very surprised at how aggressive she was. We would hookup a few more times years later. Kimberly finally fell asleep and i went to the bathroom and took yet another quick shower before leaving. I thought about just going home. I was totally spent at this point, but had to meet up with my friends and tell the about this evening i had.It was probably about 1am now and the bars close at 4am, so i just said fuck it and headed back to the bar.
When i walked in a saw one of my co-workers from the country club and he asked what i have been up to. With a big grin, i told him that i needed to get a drink and i would tell him. I was standing at the bar ordering a drink when Girl#4 approached.
Deborah was a girl i was in love with, but never made a move because i didn’t think she was interested. We would flirt and joke around, but i never took her serious and she never really gave me any indication that she liked me more than a friend.
Deborah was jut my type physically. She was about 19,20 years old at the time, 5’7, dirty blonde colored hair, blue eyes, big tits, small waist, very sexy looking. I was always surprised guys at work didn’t go after her. She was so sexy. She wasn’t slutty at all, but i guess she had a wild side. I would find out.
I was at the bar about to tell my friend about the previous girls earlier in the night and the one girl whose house i had just left when Deborah came over to the bar and sat down and started chatting us up. I couldn’t tell my friend the story with her there.
So, it is now about 230am and i was surprised she was still there. She was drinking beers and having a good time. The bar was starting to thin out. I was going to call it a night and walked over to the group of people from work that were sitting at a table. I was saying good night and Deborah asked me if i was leaving. She asked if i could drop her at her car that was in the parking lot at the country club. I said no problem. Now, looking back, she could have asked ANY of the other 4 or people people at the table to drop her off, but she asked me. I had one last beer and we headed out to the car. The country club was literally a minute from the bar we were at. The parking lot was completely empty and the only car in the back parking lot was her car. I drove to her car and parked next to her car and basically was going to say good night, see you tomorrow. She turns to me and says’ oooooh, is so dark here, hehehe’. There were no lights except for the light from the moon.
I was totally taken off guard. She says, you wanna? So, me being the naive kid i was, i said, ‘wanna what?’ She gave me this ‘you gotta be kidding me’ look with a smile. I immediately knew what she meant and she was serious. She climbed into the back on my small sports car and peeled off her clothes. I nearly came right there. Imagine secretly undressing a girl with your eyes for years and having her bare ass naked in the back seat of my car.
Thank god, i had one more condom left in my glove compartment. I had bought a box and left in my glove box because of never having a condom when i needed one. That’s another good story i will post. Despite the small back seat, we managed to have an amazing bang and dropped my fourth load of the night. We never hooked up again, but remained good friends for years. I got back home at about 5am. I recently reconnected with Girl#3 on FB and we had a good laugh.
Source: reddit.com/r/gonewildstories/comments/6980xm/m_my_wildest_night_ever