My fantasy anal deflowering

I am a young (25), fit (5'9" 128lbs run 8 miles daily) attractive (neck length auburn hair, brown eyes) woman working as a paralegal in a law firm in Washington, DC. I also have a intense desire to loose my anal virginity in the office... This is my story...

I don't when I really got interested in having anal sex. Maybe it started in college when I started going on Depo Provera for birth control. I think that is the first time that I became aware of sensunous of my butt. I got shivers the first time my doctor told me about the shot and where he was going to give it. I remember him leading me to the examination table, watching him prepare the injection and finally him asking me if I wanted a nurse present. When I said "no," he told me "you need to bare you butt and bend over the table for me Meagan." I was so nervous as I unfastened my jeans and slid them together with my panties down and bent over the table. "You're going to feel a little sting now Meagan, just relax." He swabbed one of my butt cheeks then pinched the flesh between his fingers. I gasped a bit as the needle penetrated the cheek and he injected the serum. "Alright Meagan, I'll see you in 11 weeks."

Or maybe it was when me and my boyfriend were watching porn one day and I watched a woman get fucked in her ass. She seemed to enjoy it and I was definitely curious. I started thinking about it but, surprisingly, my boyfriend (who was extremely hobophobic) associated anal sex with homosexuality and wanted no part of it. I found myself more and more preoccupied with the thought of loosing my anal virginity. When I started working at the law firm, I worked long hours.... sometimes 10-12 hours a day, often on Saturdays too. I had no time for a relationship, no boyfriend but had a yearning to feel a cock in my ass. I was getting frustrated sexually and finally one of the younger associates of the firm noticed it and, jokingly, volunteered "Meagan, I think you need to get laid girl, you seem so preoccupied land tense ately." I related how I was because of the long hours and lack of a boyfriend. He smiled and said "do you want to work it out here?"

To make a long story short, a few weeks after that initial encounter we had a very difficult case that we were working on and he asked me if I could stay even later than normal. I agreed and we worked fitfully late into the night. Finally, it was time to leave. It was well after midnight and the metro was shut down for the evening. I was stuck at the office, but Paul said "I'm going to get a room at a hotel and you're welcome to join Meagan." Then adding "No tricks Meagan, promise, no need to you to spend the night here. Seperate beds...if that is what you want." Anyway, we got the room, had my first sex in a year or so and exploded in his arms. We didn't sl**p much that night and he was definitely the best lover I've ever had with a long (8in) and thick (2in) that was just what I needed. That night was the first of many we had... at his play, at my place, a hotels... but not at the office and not in the butt.

One day he asked me what some of my sexual fantasies were. "Perhaps we can make your fantasies real Meg" he said. I blushed and told him that every since we had been having sex together, I had fantasized about him bending me over desk in the office and fucking me. "Really?" Paul said? "Yes, really!" I replied excitedly. Then I mentioned my desire to loose my anal virginity. I thought his eyes were going to pop out! "Anal, Meagan? Most women I know don't want to take in the ass, especially with a cock my size." Nervously, I asked him, "Have you had anal sex with a woman Paul?" "Yes," he replied but like I said I don't get it very much. I thought about what had transpired, what had been said. My heart was beating so hard when I realized what had been said... and not said. "Well, young lady, lets give you your fantasy" Paul said, then added "and if you want, I'd be glad you take your anal virginity at the same time." I was stunned! Paul continued "However, I want you know that my experience with the girls whom I have had anal with before, struggled taking me." "Struggled" I asked innocently. "Yes struggled Meg. You know the size of my cock and even experienced anal girls have found it quite painful taking me in their ass." I swallowed hard. "I'll be as gentle as I can Meg, but it will definitely hurt you. Do you think you can handle it Meg, do you think you can take it like a big girl?" "The first time is always the hardest on a girl but it can and does get better Meagan, especially if the woman has anal sex on a regular, frequent basis." "Is that what you want?" Nervously, I replied "Yes." "Are you sure Meagan? Because once I start to put it into your butt, its going in Meagan. All the way in. There's no backing out. There's no chickening out. So be sure you want it!" "Yes, I want it." Paul kissed me gently and told me that tommorow after work then. (TO BE CONTINUED)

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Categories: AnalFirst Time
Posted by meagan_anne_1986
2 years ago    Views: 2,254
Comments (13)
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1 year ago
Great preparation, Megan!
Lube is great!
1 year ago
Awesome, Megan. Such detail and very well written. I cant wait to read more.
1 year ago
Looking forward to reading part II and III.
2 years ago
Great story, I can't wait to read on!
2 years ago
Great beginning.
CherylHole
retired
2 years ago
Nice
2 years ago
Very good Story! I will have to read the rest now :)
2 years ago
"my boyfriend (who was extremely hobophobic)"

...afraid of the homeless?
2 years ago
That's a fucking hot story can't wait for the next part!
2 years ago
Hot story! keep em coming!!
2 years ago
Great story butt have to hear the ending
2 years ago
wow hot start, more soon please
2 years ago
Great Story Megan ! we want the rest of it !