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A Virgin Until 29

Posted by: Author: Age: 39 Posted on: 1 comments
3 likes 99 views Category: Sex Stories First Time Tags: Male-Female, Sex Stories First Time

The title is correct until I was 29 I was a virgin. I had done other things but was never able to get a women to go all the way with me. This is my story.


Growing up I was the short fat kid that most people picked on. Once I had enough I usually hit the other kid and wound up in trouble. My parents tried giving me less food but I always got more. When I was in 12 I went to a fat camp. I was 112 lbs and lost 15 and still I was the heaviest kid in school. When I was 18 I had one girl who liked me. We went out for a week and the first time she touched my dick I exploded on her. She told me to get lost and told the school what happened. My last few months of school were hell. I never went to my proms since no girl wanted to go with me. I went to college and it was no easier. I went out on a few dates and never had a second. My freshman roommate left after 3 weeks and the school never gave me another roommate. I was lonely and ate, drank and ate more. By the end of the year I was 275 lbs. The freshman fifteen were the freshman 75 for me. I was at the gym one day when the head trainer pulled me into his office and told me I would be dead if I didn't change. He then asked what I was doing that summer and I told him nothing. He made a call and I was going to be working as a counsellor at a fat camp. I went to the camp and lost 35 lbs. I was happier and more outgoing. When I arrived back at college I went to his office but he was fired and the new trainer didn't give a crap. Over the next two years I gained and lost my weight. Going into my third year at the camp I finally had a girlfriend. We met the first day when I showed her where her bunk was. She told me her name was Samantha but everyone called her Sam. She had put on 25 lbs during her freshman year and wanted to lose it. I told her I gained 75 and have lost 50 over the past 2 years. I then said I also put it back on and more. We dated all summer and we never went further than touching. One night someone rented a room and we went to party. Once we got their everyone left and they guy stopped me and told me to have some fun. He then gave me a condom and smiled. Sam and I started to kiss and soon I was naked and she was in her underwear. She then told me she was having her period so no sex. Sam jacked me off and I sucked her tits and we kissed a lot. This was the furthest I ever went. Sam lost 40 lbs and I lost 60. Once summer was over I was going to see Sam at college. About two days before I was going to leave she told me not to come. I asked why and she told me she actually had an ex-boyfriend at college and when he saw how much weight I lost he wanted me back. I turned to food, beer and more food again and put on 75 lbs. Once I graduated from college I was over 300. I looked terrible and my mother wiped her hand at me. I couldn't find work and soon I was in a book store and one of the managers quit. I went over to the head manager and asked if his position was open. She told me to fill out a form and she called up the regional manager. I heard her say he is overweight but he is always in the store. Over the next two weeks I was interviewed twice and have a managers job. I love to read and this is a dream job. Over the next year I learn the jobs ins and outs and soon I go from assistant day manager to night manager. At 25 I am still living at home and still about 300 lbs. One day a woman comes in and she is a knock out. I help her with a book she is looking for and then ask what it would take me to go out with her. She smiles and looks at me and says 100 lbs and I would date you. I laugh and she hands me her card and she is a Lori and a registered dietrition. She takes me over to the diet sections and hands me a few books and then to the bodybuilding sections and gives me more books. On the back she gives me her number and tells me to call her when I am in better shape. Over the next few weeks I read all the books and design a eating and fitness plan. I go to the gym a block from the book store and sign up. They are running a special and I pay $250 for two years. I have a trainer show me the correct way to do the 30 exercises I want and away I go. Since I work from 2:00 pm until 11:00 pm I have all morning to workout. I start off slow and do a warmup cardio, weight training and then back to cardio. I start going from 45 minutes at the gym until 2:30 hours in a few years. About 6 months in a woman comes up to me and tells me how good I look and how much weight have I lost. I tell her 45 so far and still have 55 to go. She introduces herself as Jaime. We talk for a few minutes and then get back to work. Over the next two years I see Jaime at the gym and we always talk. I never thought about her sexual and one day she happens to be in the book store and I see her. I go to her and say hi and Jaime looks shocked to see me. I tell her I am the store manager and have been here for a few years. She tells me she was picking up a book and decided to come in here. After talking for a few minutes Jaime asks why I never asked her out. I look at her and say because fat guys don't go out with good looking women. Jaime tells me I'm not fat and asks how much I have lost. I tell her 97 lbs. Then she leads me to a mirror and say look at you next to me, you are not fat. I look at Jaime and myself and say my god I'm not fat. I then look at her and asks if she will go out with me. Jaime says no, I'm going out on a date tonight. Then she laughs and says with her father. we set up a date the next night and I'm on cloud nine. The next night we meet at a steakhouse and have a great meal and Jaime invited me to her house. When I arrive Jaime has changed and is wearing shorts and a tee shirt. I am still in a pants and a button down. she asks if I want to change and I tell her I have no change of cloths. She goes into the back and comes out with a shirt and shorts. She says they are her dads and they should fit. Well the shorts are to tight and the shirt has no sleeves. I come out and she sees the shorts are tight and tell me to take them off. I am wearing boxer briefs and she looks me up and down and tell me I look good. She stands up and shows me in a mirror and I have muscles. I Flex and Jaime laughs at me. She is behind me and I feel her breast in my back. I get turned on and I get hard. Jaime looks down and asks if she was turning me on. I tell her yes is a high pitch voice. We go to her couch and she asks if I want to kiss her. I nod and we kiss. Once we break apart I smile and tell her I am a virgin. Jaime laughs and I tell her again. She looks at me and I tell her my story. My dick is now out of my boxer briefs and Jaime asks to be my first. I ask why and she tells me she has watched me change from my former self to now and wants me to see that it was worth it. She stands and strips and she is naked in front of me. I gulp and look at her hard body. I then strip and my dick is pointing right at her. I follow her into her bedroom and tell her I may cum looking at her. Jaime and I lay on the bed and after kissing she starts to stroke me. I last one minute and tell her i'm going to cum. I then cum and Jaime eyes light up and she tells me to cum for her. After I am finished she tells me that was very intense. I smile and tell her she was the first women to touch me in 8 years. Jaime smiles and says your night is just starting. Jaime lays next to me and I kiss her neck, lips, arms, breasts and then her legs. Jaime asks if I ever dined at the Y before. I say no and she tells me to listen to her and do what she says. I nod and put my wife in between her legs and inhale. The smell is erotic and I get hard again. Jaime tells me where to lick and suck and in a few minutes I hear her moan. I look up and she pushes my head down. Soon I am licking her clit and Jaimes starts to buck and telling me to keep sucking. I do and Jaime pushes my head deeply into her pussy and gives one final moan and then stops. I fell her vagina still pulsating an when I kiss then she tells me no more. When I come up for air my face is covered with her juices and she tells me I am a natural. We lay together and in a few minutes Jaime fells my hard dick. She smiles and asks do I want to leave the virgin world. I nod yes and Jaime tells me to fuck her. I get between her legs and try to slip it into her pussy. I go low and she tells me not tonight and helps guide me in. Her pussy is very wet and I slide in and slowly start to fuck her. In minutes I am grunting and tell her i'm going to cum and She tells me to give it to her. I squirt my cum deep inside her and fall on top of her. She rubs my head and tells me welcome to my web.

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