I lost my virginity to a [M]IL[F]…well at the time milf wasn’t a word yet.

From my title you could probably guess that this story takes place quite a few years ago. To set the stage a little bit, it was in the mid 90’s and I was your typical high school kid, somewhat shy and awkward, skinny but athletic. I was on the basketball and baseball team and lettered in both. I had never had a real girlfriend although girls told me they thought I was cute I was just to shy to ever ask any out, the only place I felt comfortable in my own skin was on the court or baseball field. Well that was until we got a computer and I was introduced to AOL chatrooms. All of the sudden I could talk to girls and if one didn’t like me, oh well on to the next and so on. And this is where my story begins, some of the conversation has be paraphrased because I don’t remember exactly what was said, but you’ll get the gist of it.

I was on Christmas break so naturally I was staying up as late almost every night chatting away and I was just about to call it quits and go to bed when I got an instant message from a random person that just said “hi”. The screen name was obviously meant to be feminine so it immediately caught my attention, upon quick glance of her profile she seemed to be a real person and quite a bit older than me. I replied back timidly thinking that this is probably a mistake and she clicked on the wrong name. And to my surprised she began engaging in conversation and was very easy to talk to. I even picked up that she was flirting with me a bit. At this point I’m thinking this has to be a guy but my keen bullshit meter that I acquired from the past year of chatting online wasn’t really pinging. I learned that she was 32 years old and that she was a nurse. She asked me about my extracurricular activities and what my plans after high school were. It was a pleasant conversation and I added her to my friends list before we said our goodbyes for the night.

The next night I signed on just to see if she was online and to my delight she was and she IM’d me before I had a chance to write her. “Hey cutie, how was your day” popped up on my screen and immediately replied back. We picked up right where we had left off the night before and she was definitely flirting more and more as the night went on. I slowly lowered my guard and started flirting back because I just couldn’t find anything to suggest that she was lying about who she was. I sheepishly asked if she had a picture, which was kind of uncommon back then since no one had camera phones and you actually had to scan a picture that was already printed. All of the sudden, “You’ve got mail” came through the speakers and I quickly opened the message to clicked on the attachment. After a few seconds the pixelated image came into focus and I was looking at a bleached blond with dark green eyes and her shirt could barely contain her huge tits. All the blood rushed from my brain to my cock and I was speechless. Could I really be talking to this woman? My instant messenger pinged, “are you still there? did you get my pic?”, all I could muster was “wow”. She replied with a :). Up till this point she had been driving the conversation but I decided to take a chance but my teenage brain could only come up with one question, “how big are they?”. “36DD” she replied. “Are they real?” this was what I actually said, still embarrassed by it today. “Real expensive” she joked back. We both had a good LOL.The conversation got more explicit after that, all inhibitions were out the window. She asked me to measure my cock both the length and width, I reported back with 7″ long and 6″ in circumference. Then came the question that made my heart jump out of my chest, “do you wanna meet?”. I didn’t know what to do, there were stories all over the news about bad things happening all the time to people who met strangers off the internet. I wanted to have sex with her so bad I thought it’s worth the risk. I quickly devised a plan in my head to meet in public first and if she wasn’t the person from the picture I would leave. She gave me her phone number and we planned to meet at the mall by her house the next day. That night I couldn’t sleep, I was so excited, horny and nervous all the same time. I must have jerked off 4 times before I finally dozed off.

The next day I called her, my hands were shaking so bad I could barely dial the number. A woman answered, ok good start so far. She was friendly and had this sexy raspy voice. We agreed on a time and specific place to meet, a Wendy’s parking lot next to the mall. I got in my car and started off, it was about a 30 minute drive and it was dark by the time I got there. I arrived first and began to panic and horrible thoughts starting swirling in my head, “this was all a hoax, at any moment people are going to come out with a camera and point and laugh”. But then a white car pulled up next to me, it was similar to what she described and I looked at the driver who was looking right at me. It was really her, she smiled and waved me over to her car. I got in her car and we talked a little bit and we left for her house.

We walked into her home, it was dark except for the light coming from the bedroom. She took my hand, led me back and told me to sit on the bed. She shut the door and as she turned around she began unbuttoning her shirt and I could catch glimpses of her dark green bra as she moved down each button. She was standing right in front of me as she opened her shirt and her huge tits were just inches from my face. She took my hands and placed them on her chest and I’ll never forget the sensation of feeling my hands overflowing with boob and how heavy they were. I instinctively began to squeeze them and I could feel her nipples through her bra which became the focus of my attention. She took off the bra and I began to suck on her nipples until they were rock hard and she began to moan softly. She instructed me to take off my clothes, I was fumbling around nervously and when I looked up I noticed she was laying on the bed in just a thong that matched the bra she had on earlier. I was in awe and had to just stop and stare, she was small in stature only about 5’1″, 125 lbs and had a very small waist which looked even smaller when her large tits weren’t confined to a shirt and bra anymore. I felt my cock trying to escape my boxers and I saw her eyes focus in on it. She moved to the edge of the bed and began stroking my dick through the fabric with her eyes locked on mine and gave me a mischievous smile. She pulled my boxers down and I could feel her breath on the head of my throbbing cock. She looked up and said “wow you weren’t lying about being thick” and began to stroke me harder. She pulled me towards her by my dick and told me to lay down on the bed. She positioned herself on her knees and elbows between my legs and began to suck my cock in long slow movements as she used her hand to stroke what wouldn’t fit in her mouth. It felt incredible and the view was even better, she was still wearing the thong and her ass was in the air moving and flexing with every pump. I was going to cum soon at the current pace so she slowed down and came up and began kissing me and removed her thong at the same time. We laid there kissing and I moved my hand down to feel her shaved pussy which was dripping wet. I slid one finger inside which caused her to let out a small moan and I began to work it in and out. She was thrusting her hips to my movement and we were in rhythm. She asked if I was ready, and I wasn’t sure what she meant but still said “yes”. She got up on her knees and straddled me. She reached down and stroked my cock as she rubbed her pussy against the tip to make it nice and wet and slowly pushed down until I was inside of her. All of my senses were going wild, I could feel the warmth and wetness of her pussy around my dick, her skin was so soft and silky against my body as she began to ride me, her enormous tits were bouncing in my face. She began to moan loudly and she worked my dick faster and faster, then she was calling out my name. I honestly didn’t know what to say so I just stayed quiet and let her ride me till she had an orgasm and laid on top of me panting. After she caught her breath she began to suck and stroke my cock, within a few minutes I was on the verge of cumming and she told me she wanted it in her mouth. As I came she squeezed my balls and milked every last drop into her mouth.

That was it, that was the beginning of my fetish for older women. We met up a few more times in the following months, she was training me and I was definitely willing to learn. Our last encounter occurred when I was in college and that’s when she revealed that she was married and had a family but he didn’t mind her “having fun”. She asked me to fulfill a fantasy she had always had and I agreed….

Part 2 may be coming soon…

Source: reddit.com/r/gonewildstories/comments/7t5iun/i_lost_my_virginity_to_a_milfwell_at_the_time