First Time Getting Pegged [24M with 24F] [Part 3 A] [Prelude]

This is a continuation of my previous posts about my Fist Outdoor and First Anal Experience.

We had started fucking like rabbits post our initial meets. I would go to her place almost everyday post work and stay over on the weekends. If we did not meet on a particular day because of any reason, we would fuck on video call, if not that then voice call, not that then over texts. We made sure that we came to each other at least once a day. We’d talk a lot after sex. She’d share her experiences, I’d share mine(which didn’t last long). She always attracted female attention along with guys. A lot of her female coworkers would play with her. I always joked about including me in these sessions, I mean would would want to be included.

Our lives started to revolve around each other. We started going out for dinner on Fridays and Saturdays. Fridays would be discovering new places and on Saturdays we would return to our favorites. I was extremely vanilla before meeting her, shes fully responsible for my sexual awakening. We would request for corner tables at restaurants. I always liked quite places to dine and they turned her on for some reason. It started with us making out during dinner, slowly graduated to hand play. Either I’d finger her or she’d give me a hand job. There have been times where we out right had oral sex at some restaurants. Never dealt with penetration though. If she every wanted to have sex in public we’d go to the movies, i always preferred a late night show as there wouldn’t be a lot of people around.

Now this particular instance happened 2-3 months into our relationship. I went to her place, i am pretty sure it was a Saturday. She’d walk around naked in her house or in panties at the most when shes expecting me. She’d put on a long tee or a robe to get the door and then as soon as i am in, she’d take it off. This time, when i knocked on her door, she opened wearing a tshirt, had short gym pants underneath and was also wearing a bra. I quickly realized that she had company. I asked her at door if it was okay for me to come in, and she said yes. I had no clue who the guests were. As i entered the living room, i saw this B.E.A.utiful woman sitting on the couch. I mean my girl looks good don’t get me wrong, but if shes a 7 then this stranger was a 10 and then some. She was about our age, wearing a brightly colored crop top and a pair of denims. I could see her sheer black bra underneath when she’d stretch to get something. Her boobs weren’t as big, maybe a C Cup. She was shorter than my girl by a couple of inches but she was extremely fit. I could see the contour of her abs on the exposed mid riff. Next to her was a guy who looked at least 5-7 years older than us.

My girl told me that the female was her best friend. The couple was engaged and were here to invite us to their wedding which was in a few months. We sat there talking for a couple of hours. The friend would tell us stories of my girl’s slutty-ness and then my girl would tell slut stories of the friend. Me and the other guy would look at each other and wonder what kind of fiends had we gotten in bed with. During the stories i realized that this female was one of the girls who’d fool around with my girl.

As soon as they left, my girl jumped on me and started kissing, i picked her up and she locked herself around my waist. I took her to the bedroom, and lay her down. I was about to ask her regarding her friend and she stopped me. She said she knew what i wanted, she could see the lust for her friend in my eyes. I told her that i didn’t just want to fuck her friend, i wanted her to participate as well. She took that pretty well, i was expecting a slap across the face or something. She the told me that she’d talk to her friend about a threesome only if i was able to make her cum with anal alone. Now, I was never able to get her to orgasm via anal alone. I always had to resort to nipple play or eat her out or penetrate her vaginally to make her cum. To add to my problems, she said i only get one shot, if i cum before she does, then its over.

I take a deep breath, and reach for a condom. She slipped out of her clothes by the time i put it on. I spread her legs and got on top of her. Pushed my dick in her ass and hoped for the best. The problem was that her asshole was too tight and didn’t have enough experience with it. Within a couple of minutes i reached my limit, i tried to reach for her tits and she warned me that it wouldn’t count. A few more seconds and i was done.

I looked at her in disappointment, she came close and gave me a kiss. She asked me if i really wanted to fuck her friend, and i nodded like a little kid. She said she’s willing to give me as many chances as it took but there was no way getting around making her come with anal alone. I almost jumped with joy and started kissing her. She stopped me, got on top and told me that it’s going to cost me. I asked her what would it take ? to which she replied that she’d peg me once before every attempt. The expression on my face dropped.

P.S. I am currently writing the Main Act. I didn’t think this would turn out to be this long hence breaking it into ‘Prelude’ and ‘The Act’.

Source: reddit.com/r/sexystories/comments/u12c1k/first_time_getting_pegged_24m_with_24f_part_3_a