A brief history of nearly all my sexual conquests. [Clare] | 2016

Clare

Clare was my third girlfriend and we met on the same dating website as my previous sexual tryst, Renee. The first time we had sex was an impulse decision on both accounts, it was 3am on a Saturday morning and we were texting after having both gone out for the evening with friends. She invited me over and I obliged, catching a taxi to her flat the next suburb over.

She was four years older than me and very good looking, though you wouldn’t know it from her insecurities. In her mind her platinum blonde hair, perky C-Cup breasts and firm ass that can only come from hours in the gym weren’t enough for guys. She was comfortable being naked however she felt her body should be better and it showed in her personality. My thoughts on her showed in a different way and for our first dozen sexual encounters I suffered from premature ejaculation. Nevertheless we got over that and began dating three weeks after first having sex, including one very memorable occasion.

Due to timing more than anything else I was due a visit at my parents and Clare came along for the ride. She got on well with my mother, better with my grandmother and better yet with my brothers. It was wonderful to see how she mingled so well with everybody. That night we went to the local pub for some beers and she used it as an opportunity to show off, sticking her tongue down my throat at every available opportunity. The more she drank the more she tried to dry hump me until eventually I decided to take her back to my mother’s house to save her further embarrassment.

Upon arrival she went to the bathroom while I stripped down to my underwear to get ready for bed. As I began to climb in Clare returned to the room completely naked and in pigtails. While we had discussed my enjoyment for pigtails before she had never acted on my fetish and this came as a welcome surprise. With a confidence I have yet to see matched she strode over to me, dropped to her knees and took my cock from my underwear to place in her mouth. The sensation hit me all at once and I quickly felt myself stiffen in her mouth as she sucked and slurped happily at my cock with an over the top level of enthusiasm. I grabbed hold of a pigtail with each hand and began to use them to steer her head, pointing it in the direction I wanted her to go. When I moved it down towards my balls she obliged, gently nibbling and kissing my sack like two delicate peaches.

Moving her head down further she continued to oblige, licking at my taint and running her tongue up to my balls in a way she had never done before. This was all new territory for us and yet Clare was somehow enjoying this more than I was. I decided to push her a little further and rocked my hips back, elevating my ass in the air. With no more hints needed Clare began to lick and tongue my asshole in the same way she had my balls. It was amazing. The feeling washed over me as she ate my ass and I used her pigtails to push her head, and subsequently her tongue, deeper into my ass as she continued to oblige my every wish. After several minutes of having her eat my ass I grabbed her pigtails and jerked her head towards my cock. Somewhat reluctantly she began to suck my again and I made a mental note of the fact she enjoyed eating ass more than she did sucking cock.

Rather than using her pigtails as a guide I used them as handles as I began to thrust my cock in and out of her throat. Clare obliged by cupping her hands around my ass so I had better access to the back of her throat and I took full advantage of it, thrusting and making her gag until she had a large amount of spit running down her chin and onto her perfect breasts. She stopped only for air and continued to suck me like her life depended on it. As I felt the familiar build up of an orgasm begin to build I let her know I was going to cum shortly. She ignored this in favour of sticking my cock as far down her throat as it would go and as I felt myself about to cum I used her pigtails as handles and thrust myself as deep as I could go.

A thick, warm wad of cum shot deep past her tonsils and into the back of her eager throat. Clare gagged as wave after wave of thick cum poured into her mouth and opened her mouth wider to allow that which could to drip out onto the floor. As the last load shot into her pretty little mouth I took my cock out of her mouth and she looked up at me. Her eye shadow had run and her face was covered in spit and cum but she had a large smile on her face, pleased that she had given such a good blowjob. It took several weeks to convince her to eat my ass again and she never wanted to deep throat quite as deeply again but she had nonetheless given me the best oral sex of my life up to that point.

That was Clare.

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