This is the true story of how I lost my virginity.
I was 13 and my Mom’s best friend Terri had recently walked out on her husband after finding out he was cheating on her. Terri at the time was 46 years old and very attractive (to me at least) for her age, red hair with some gray, about 5’6” tall, she was a large lady but not nasty large I guess a small BBW would be a good deion of her. She had a nice round booty and big tits DD or DDD depending on which one of her bras I checked out. Terri came to stay with us for about a month while her husband moved out of their house and she got her stuff together. While she was staying with us she walked in on me in the bathroom as I was getting out of the shower, she only saw me for a minute but she saw everything.
I was nothing much to talk about, average kid, a little short for my age but in the shower at school I was always bigger than the other kids. Some of them would tease me about it but it never bothered me much as I knew they were just jealous. It was about a month after Terri moved back home that she called my mom and asked if she could “borrow” me for a day as she had some chores she needed a “man” to help her with. My mom volunteered my services and the following Saturday she dropped me off at Terri’s at around 8am. Terri was turning the basement into an office and needed help moving stuff in the basement and carrying stuff up to the attic. It was July and it was hot, Terri didn’t have AC anywhere but in her bedroom so it was hot and stuffy in the house. The basement was cooler so working down there wasn’t bad but once we started carrying things up to the attic we got sweaty.
Before we started moving stuff upstairs we took a break for some cold drinks. Terri had always been a favorite of mine, I always thought she was hot and when she hugged me I would get lost in those huge titties. We talked as we rested and she started asking if I had a girlfriend. I said no, and she said that was a pitty from what she had seen. I knew exactly what she was talking about because she had become a masturbatory favorite of mine where instead of walking out of the bathroom that day she closed the door behind her and we did everything my perverted little mind could think of. I blushed and she told me she didn’t mean to embarrass me, that I certainly had nothing to be ashamed of and that most men would give their right arm for what I had. I just kind of stammered out something unintelligible and seeing my discomfort she suggested we get back to work. She gave me a big hug which got my already growing cock rock hard and I know she felt it pushing into her thigh.
The attic was basically a hole in the ceiling on the second floor, it didn’t have one of those drop down ladders so we had to get a regular ladder from the garage to get up there. We fell into a ritual where we would pile stuff up in the hall then Terri would hold the ladder steady as I carried things up and arranged them in the attic. I was wearing a pair of loose shorts and I had gotten into the habit of not wearing underwear because all my mother bought me were tightie whities and they were mostly uncomfortable especially when I would get excited. I was up at the top of the ladder moving some boxes away from the hole so I could climb up when I felt Terri’s hand on my thigh just above my knee. I had been semi-hard ever since our discussion and hug and when I felt her hand touch me I went full on hard. I looked down and she was looking up but not at me but at the incredibly obvious hard on I was sporting in my pants. Her hand slid up my thigh into the leg of my shorts and I felt her begin to rub my balls. My knees got weak and I almost fell off the ladder, she looked right into my eyes and asked if Iiked that. I nodded yes and felt her hand wrap around my cock and begin to stroke me. She asked if anyone had ever done this to me before and I shook my head no. My mouth was so dry I couldn’t talk. She then told me to relax and enjoy. She took her hand out of my shorts grabbed them with both hands and pulled them down. My cock sprang out hitting my stomach. She grabbed it again and standing on her toes she slid her mouth down over it. I had jerked off many times but nothing had ever felt as good as this and I came almost immediately. I tried to warn her but she either didn’t hear me or care because she took my load in her mouth and swallowed every drop. She kept sucking until it became uncomfortable then as she was rubbing the head on her lips she looked up at me and asked if I liked it. I couldn’t tell her how much I liked it quickly enough and sounded mostly like a babbling idiot. She said she enjoyed it as much as I did but it had to be our secret and we could do it more if I didn’t tell anyone. I readily agreed and she said it was time for my first lesson.
She took my hand and led me into the bathroom where she stripped and we got in the shower as she had me wash her she explained the different parts of her body paying special attention to her pussy and clit. Once I had washed her she started washing me. Of course I was rock hard again. She said that she had forgotten how good a young man was got on her knees and sucked me off again. Thankfully this time took a little longer and once again she swallowed my load. We dried off and she led me to her bedroom, she lay down on her back and had me get between her legs. Then she gave me the first of many lessons on pussy eating. She had me start by kissing and licking her thighs slowly making my way up to her pussy, she had me run my tongue over her lips nibbling on them and pulling them with my lips, sliding my tongue back and forth between them and pushing it inside her. All the time she had her hand on the back of my head guiding me and telling me what to do. After sliding my tongue in and out of her a few times she guided my head up to her clit where she had me make little circles around it with the tip of my tongue then flick it back and forth across it. She started to become very animated moving her hips up into my face and holding my head tighter against her pussy. Her clit was big and all I could think about as it was rock hard against my tongue was that it was like she had a little cock. So without her direction I wrapped my lips around it like she did to me and started sucking it in and out of my mouth. She started to shake all over and cried out as she mashed my head into her pussy. She started telling me to not stop as she continued to cum all over my face. She didn’t squirt but she got really really juicy. She grabbed me with both hands and pulled me up on top of her thanking me as I got my first real kiss. Her lips were soft and gentle and she told me to slow down, loosen up my lips to make them soft and we kissed for a bit as she ran her hands over my back and butt. I was grinding my hard cock into her belly. Next lesson she told me. Rolling over so I was on my back and she was straddling my waist she asked if I was a virgin. I said yes and she said not for long. She reached behind her and started to stroke my cock and then slid her bottom back grinding it on my cock. I felt her rotate her hips back as she sat up and the head of my cock fell into the hottest wettest most amazing feeling I had ever experienced. Then she started to slide back and down and I lost my virginity as her tight wet pussy slid down onto my cock until I was balls deep inside her. She moaned as I slid into her and I knew I wasn’t going to last very long like this. She didn’t move up and down but started to just rotate her hips forward and back then in little circles. Her big tits just swaying above me as she did. This was the most amazing thing I had ever felt and I told her I was going to cum. When she heard that she started to ride me hard and fast and we ended up cumming together. She collapsed down on top of me and we kissed for a long time with my cock inside her and her slowly grinding her pussy on it. I grew hard inside her again and she sat up and started to ride me moving up and down with long slow strokes the length of my cock. Her tits started bouncing and swaying and I was mesmerized. She leaned down lifting one of her tits to my face telling me to suck it. I gladly took that fat nipple into my mouth as she started riding my harder and faster. She told me to bite her nipple gently and I did and she started cumming on my cock. As she collapsed on top of me I was fucking up into her and she rolled me over on top of her and told me to fuck her. Instinct took over and I started to bang the shit out of her pussy until we both started cumming again. We lay there side by side after making out and talking when the phone rang. It was my mom asking if Terri wanted her to come pick me up. Terri told Mom that we didn’t get nearly as much done as she had hoped for, that we hadn’t eaten yet and if she didn’t mind she would like to keep me for the night so we could get an early start in the morning. Mom agreed and I started getting hard again thinking about spending the night with Terri. Terri noticed my reaction and dove down onto my cock sucking it like a woman possessed. She threw her leg up over my head straddling my face and pushed her pussy onto my mouth. I started eating her and I could taste my cum inside her. I wasn’t grossed out because I regularly lick my cum off my hands after jerking off. We came together and ended up falling asleep in each other’s arms.
I woke up to the most amazing feeling and it took me a few seconds to realize where I was and what had happened but it all came together when I felt Terri sucking my rock hard cock. Best way I had ever been woken up. She swallowed my load again and crawled up on top of me kissing me. I could taste my cum in her mouth and I started kissing her hard. We ended up fucking 2 more times before morning. Then spent the rest of the next day fucking and sucking our brains out only taking breaks for food and water. Terri was sucking my cock when my mother rang the doorbell to pick me up. I came down her throat and got my pants on as Terri opened the door thanked my mom for letting her use me and gave me a hug and a kiss on the cheek as I walked out with my mom. Terri and I spent a lot of time together that summer I would sneak out at night and she would come pick me up and we fucked like newlyweds.
She told me her husband has a very small cock and when she saw me she was amazed that my soft cock was about the same size as her husband’s was when he was hard. She had only had 5 sexual partners before me and 2 of them were women. She ended up divorcing her husband and we continued to see each other on and off even after we both married. She became very sexually active and eventually introduced me to several of her girlfriends. But those are stories for another day.