38 Yr F (me) Sex W.16(m) Friend Of Daughter
At the time this happened I was a 38 yr old single mother living with my 14-year-old daughter and casually dating my next door neighbor 10 years my senior. The guy my daughter was dating at the time was her first serious boyfriend (he was 14 or 15 as well) and the first guy she had ever brought over to our house. I say that because it wasn't like I was used to her always having teenage guys around the house. This was actually very new for me.
One night his older brother (who was i believe 16 or maybe 17 but definitely not older than 17 because he was a junior in high school at the time), came over to our house to pick up his younger brother. After pulling up in our driveway blasting his music insanely loud he got out and came inside the house to use the restroom. This meant he had to pass in front of my bedroom door which was open.
It was around 10:00 p.m. and I was already laying in bed practically naked, which was how I mostly slept back then. At this point in my life I went through phases where I would sometimes smoke weed occasionally and it just so happened I had taken a bullet about 15 minutes before he arrived. As he passed by my door he saw me laying in bed, said hi, introduce himself, and told me he just need to use the restroom really quick before they headed home. I didn't know if he smoked weed or not but I could tell that he definitely smelled it lingering in the air. After using the restroom he went back out to the living room I thought nothing more of it. Well, a couple minutes later my daughter came in and asked if I would get her boyfriend's brother high before he left. I was honestly more annoyed by this request than anything else because I didn't want to have to get dressed or entertain anyone since I was already somewhat buzzed and high as it was, I had already settled down for the night and was watching TV in bed, and the last thing I really wanted to do was get a 16 year old kid high while we made awkward small talk in my bedroom. But next thing I know before I could think of a reason to say no he was standiing in the doorway.
So I said fine, I would smoke a bowl with him provided that he hand me my t-shirt from off the dresser and turn around while I put it on.
Doing anything remotely sexual with him was still not even a passing thought at this point. At that point in my life I no longer really looked at teenagers in a sexual way. As far as 16-year-old girl, he was a good looking guy, six feet tall, athletic build, broad shoulders, dark hair, nice jawline, etc...but it wasn't really something I was thinking about.
I handed him the bowl to hit but did not smoke any myself. I was already feeling awkward enough about the situation having this 16 year old stranger sitting at the foot of my bed while I am under the covers half naked letting him hit my weed bowl. At first I felt a little awkward and anxious about the whole thing but his personality put me at ease. He was actually pretty funny and entertaining. Oh and did I mention, super charming and aggressively seductive? After about 5 minutes past and he finished smoking it was like a switch flipped and he went from being a normal 16-year-old getting high on a Friday night to one that was solely focused on seducing an older MILF. I remember she said something about how cold it was in my room and how he would be a lot more comfortable if you could come sit in the bed with me. I remember before I could respond he looked at me and said, "and I bet you will be more comfortable if I come sit up there too." At that point I knew for a fact he was flirting with me and being very sexual in his suggestions and it was around this time that I started contemplating the possibility of what if...
Long story short, he eventually succeeded in his seduction and I can't say that I put up very much resistance. Within 15 or so minutes of meeting this young man and within 10 minutes of him entering my bedroom and within 5 minutes of him climbing into my bed and within probably a minute of him slipping his finger in my dripping wet vagina I found a 16 year old deep inside me, in my bed,
But the truth of the matter is that on that night I had some of the most amazing sex I've ever had in my life. He fucked me really good for a solid 20 minutes before asking me if I was on the pill. I kind of laughed and said no but my tubes have been tied to which he responded in the cutest way ever by saying, "what does that have to do with anything?” He had no clue what I was talking about! But I knew exactly why he was asking. So I told him he was welcome to finish inside me. Which he promptly did.
After we were finished we hung out for another 10 or 15 minutes. I got him high again and as he was leaving had my daughter go out to their car before they pulled away with the excuse that if he came back inside I would give him some weed to take with him. Which I did, after he fucked me again for another 10 or 15 minutes, this time from behind and really rough, even slipping it into my asshole (without even asking or saying he was going to do it) for the last couple minutes. I have never been a big fan of butt sex but I have done it a few times so this wasn't my first time around. But it was the first time somebody had just took it up on themselves to do it without even wanting me which I found oddly erotic. I would even go so far as to say this was the only time I ever found butt sex pleasurable. Ever.
A lot of women in my situation would make excuses and say they were going through a rough patch or they were drunk or they were just looking for attention and they normally wouldn't do something like have sex with a 16 year old... And while it's true this was the only time as an adult I ever had sex with a 16 year old or a teenager for that matter, I wasn't drunk or going through a rough patch or confused about anything in life.
Everything was relatively normal. I owned my own hair salon and made decent money, own my own house my own car, and was actually in a relationship with a man who lived right down the road. It was not uncommon for this man who is my boyfriend at the time to just pop in and out without calling first since he lives so close. I talked to him earlier in the day and knew that he was going to be working on his car with a couple of friends of his and drinking in his garage. This meant he may or may not come over anytime. And while I obviously would have preferred to have not gotten caught having sex with a 16 year old behind My boyfriend's back, let's just say the reward outweighed the risk in my mind at the time. Judge me all you want for having sex with my daughter's 16 year old friend when I was 38 but the truth is if I'm being totally honest, the only regret I have about the whole thing was only being able to do it this one night. It was fun having carefree sex with a hot guy who knew how to fuck me and had a nice dick that was attached to a nice body to do it with. It definitely beat letting my sloppy drunk 49-year-old at the time overweight not very attractive boyfriend get on top of me with his semi hard dick and flop around for 2 or 3 minutes.
I think most women if they were being honest with themselves imposed with the question would you rather have sex with a hot 16 year old who's going to give it to you good or the fat 49-year-old who's going to make you feel nasty, almost 100 out of 100 women would fuck the 16 year old... And if they say they wouldn't, they having sex with a 16 year old wouldn't do anything for them, it would make them feel dirty blah blah blah, all I have to say is ..(continue confession)
