I have a lot of sexual stories that stir in my head and bring be back to some intense orgasms and taboo moments. I wanted to write them down and share with others these amazing times in my life that I would love to relive over and again, what better way than to write down.
This is the first time that a woman had touched me and what I like to think was the defining moment in my sexual life. This single orgasm has stuck with me to this day as a 30 year old married man, and today I still find myself chasing that euphoric orgasm and exploring something so taboo.

I was 13 years old when I had my first assisted sexual experience. My mom and dad and recently been divorced and my dad was facing a mid-life crisis and began dating trashy women. The kind who have multiple babies from multiple fathers, smoke a pack a day, voices strained by the years of whiskey abuse, and bit chubby from the baby weight. My father began to date this one woman Shelley who would constantly throw late night parties at my dads new home, many a times resulting in the cops being called and him very close to losing my visitation rights. I remember trying to fall asleep and hearing the clinking of bottles and the smell of pot seeping underneath my door as I tried to sleep before school the next day. It never bothered me and actually began to excite me when I met Cindy one of Shelley’s friends….

Eventually I stopped trying to sleep and would sip one or two beers along side my dad until him and Shelley would sneak off and fuck loudly in their room. In this time I would sit and talk with Cindy who was a permanent fixture at these parties. She always seemed to interested in me. She would ask about school and how I must be getting all the girls attention. She would warn me not to knock any of them up or I would pay for life, blah blah blah. Cindy had two kids herself that I didn’t know but spent most of the time at their dads. When I expressed to Cindy that I was shy with girls and could never get one to kiss me, that’s when she began to encourage that I should masturbate to the thought of all those girls at school and this would ease the tension and make me more confident (made sense at that age), today I think she just wanted to talk dirty to me without crossing any lines. Yet shortly after that conversation, that line was crossed.

I took the school bus home from junior high to my dad’s house only to find that he was not home and I was locked out. I walked down to a pay phone and tried to call my mom but she was not answering. I called my father and he said he was up in Palmer, a couple hours drive from Anchorage. I remember being freaked out and feeling alone and kind of pissed at the world for something so simple as being locked out. My dad told me to hang tight and wait because he would send Shelley to come pick me up and hang out with her for the evening until he drove back. I sat on the porch and had no idea what was in store for this evening…

A car pulled up to the house and it was not Shelley, two honks and I realized it was Cindy. She had told me that Shelley couldn’t get off work to get me so I could hang out with her until one of them could open the house for me. I remember feeling at ease once I got in the car and excited to hang out with Cindy. I of course didn’t think anything sexual might happen, but just knew she would be fun to talk to. She asked if I was hungry and took me to the McDonalds drive through and got me some food. She was so playful in the car and asked me to feed her as she drove. My finger slipped into her mouth as she took a bite from my hand and before letting it go she sucked the tip firmly. At that moment I was hard immediately and kept replaying that sensation in my head wondering if it was an accident or if I had just made it up. When we got to her house Cindy said she needed to change and gave me the remote to watch TV in her living room. The house was a total mess and smelled like moldy laundry. Kids toys were scattered on the floor and fast food containers covered the tables and counters. As I sat there I kept thinking about Cindy sucking my finger in the car and it made me want her. Cindy had to have been mid 30’s if not older at this time. She had long reddish hair that came down to her butt, She always wore faded jeans that were tight fitting and what I though at 13 wasn’t exactly sexy. It wasn’t until Cindy came out in small grey shorts and an over sized looney-toons bed time shirt which clearly showed her large breasts. She was not wearing a bra and they bounced gently as she walked around the house. Cindy came to sit next to me and caressed my leg asking if I needed anything. It wasn’t sexual at all but again I was hard instantly and I remember pressing my forearm down on my lap to conceal my hard on which made it feel even better. Cindy began to make small talk about school, girls and lead into a conversation about how my masturbating was going. I remember being very embarrassed but eager to tell her. Cindy dominated the conversation and began to mention how the girls at school must have small breasts and asses. She would laugh often after making a sexual comment and then avert her attention to the tv. I mainly nodded and laughed along with her.

I will never forget this moment and it is engrained in my mind, such a vivid image. Cindy turned to me and said do you like my tits and lifted the looney toons shirt exposing her large tits. Her nipples were huge and for the longest time I though all women had dinner plate nipples… Cindy was a bbw, and had a tummy on her with baby scars. We both laughed when she flashed me and she encouraged me to flash her. I lifted up my shirt and she smacked my flat stomach and mentioned how fit I was. From here it turned into a flashing game. We would sit and watch tv and Cindy would slide over her shorts exposing a very red bush. She would continue to pretend like it was no big deal and keep watching tv until she grabbed my hand and slid it up her thigh and in through the leg hole of her shorts. It was so hairy and warm in there. She used my fingers to spread her lips and I felt the wetness. My hard on was raging now and I had no idea what to do. That was no problem because Cindy took control. She kept my finger running up and down her pussy and began to moan softly. She pulled my hand out and slid it in her mouth tasting her own pussy, I now knew that the finger sucking from the earlier McDonalds meal was no accident. Cindy asked me, “Do you like me?” I answered with a shaky voice and let her know that I liked her a lot. She lifted my shirt and began to kiss my stomach and scratched my smooth chest with her long nails. She stood up and exposed her body to me, first she slid down her grey shorts and there it was a full red bush between her thick chubby legs. She removed the looney toons shirt and exposed two very large breasts. Cindy got down on her knees just in front of the couch and laughed, nervous habit? She asked if I wanted to undo my belt of which I did very quickly. Without her asking i took of my pants and exposed a huge erection through my boxers. Cindy pulled my hard cock from the hole went down and put her lips around it. This was the beginning to a feeling that I have been chasing ever since. I remember it being so warm and feeling her tongue slide up and around my cock. I remember the slurping sound and her taking on my cock which fit perfectly in her mouth. I was about 5 inches hard so she had my entire cock and balls working her mouth, it was amazing. She moved up and down with her lips and moaned loudly. She used her long nails on my stomach and would grab my small ass shoving me down her throat. What could have only been 5 minutes I quivered and began to pump in her mouth. I remember trying to pull out my sensitive cock from her mouth but she refused pushing me down and vacuuming up my cum until every last drop was down her throat. I lay back and my cock was tingly still in her mouth but soft now. She kept it in her mouth for at least another 2 minutes, assuming she was trying to get my hard again but it was a no go. She stood up and laughed and began to dress. I told her that I wouldn’t tell anyone and she laughed at me. we sat on the couch and watched tv until my dad showed up 3 hours later to bring me home. I got home and went straight to the bathroom to masturbate, eyes closed and trying to cum to the though of Cindy. It was at this moment that I knew stroking my own cock would no longer do. I knew what pleasure felt like and I wanted it.
I never had a sexual experience with Cindy again. Eventually my dad left Shelley and her trashy friends behind. I thank her for such a wonderful experience and to this day know she is the reason I am such a sexual person, a sex addict.

-AJ

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