That time I got DP’d by my then BF and his best friend

I have made it a little goal of mine to experience alot of things sexually before I am too old and get married/kids etc. This was with my then boyfriend at the time Dean.

Dean was dark skinned and played basketball at the college we both attended. We met at a party and really hit it off and it wasnt long before we were a thing. Dean had a few friends but there was one guy he was particularly close too (Shaun).

The sex with Dean was amazing, he was well hung and stretched my pussy every time we fucked. I loved the feeling of having something in my ass while we fucked so often he satisfied me by sliding a finger or two into my tight ass while we fucked or inserted a plug that he picked out himself.

We often joked about me getting tag teamed and DP'd and used it as dirty talk while he slid inside me. I hadn't let Dean in my ass before, the thought of him stretching out my ass like he did my pussy was something that scared me. This was something I was going to have to overcome if I was going to go through with this.

When we talked about who we would do it with, we both said we'd prefer someone familiar as opposed to a complete stranger. Dean mentioned that he brought it up to Shaun and that he had secretly expressed his desire to fuck me. I had heard rumours that Shaun was pretty hung himself. Dean confirmed my suspicions saying that my pussy and ass were going to be tested.

I decided that I probably needed to train my ass in order to handle both guys simultaneously and still enjoy myself. So i decided to buy myself my own little anal training kit. A shit load of lube, two butt plugs of different sizes (1inch diameter and a 2.5inch diameter one) and a 8 inch dildo that widened to 3 inch at the base. They we pretty big to say the least. I gave myself a week of training before the big day. I told Dean that there would be no sex for the week while i spent some 'me' time.

Each night I locked myself in my room and spent a couple of hours stretching my little ass. I started small but by the end of the week I could reach the base of the dildo and could wear the butt plug out while shopping for groceries.

I told Dean i was ready and Shaun they both came over that same night. We started off drinking together and having a good time. I sped things up when I returned from the bathroom in a little thong that could barely cover my asshole when I bent over in front of them and a see through bra.

They quickly got the message that it was go time and I begun sucking them both off while they sat on the couch drinking their beers. I got in a position where I was sucking Deans cock while Shaun worked on my ass and pussy with his tongue and fingers. It wasn't long before I was being spit roasted and I couldn't help but laugh as I was that white girl satisfying two well hung black guys.

I alternated who I sucked and who fucked me a few times before I decided it was time for the DP. They rock paper and scissored who would get to choose which hole they wanted first. Shaun won and decided he wanted to break my ass in first. I straddled Dean and slid right down onto his cock. I leaned forward and spread my ass to make it easier for Shaun to enter. He slid in and I am glad that I had did my training as it prepared me well. However I did not account for the feeling of both holes being stretched and filled simultaneously. I held my position while they both fucked me slapping my ass, tits and face. I made no effort to silence my moans as the feeling was like ecstasy being filled and stretched. After awhile they switched positions and Shaun was in my pussy. I was on birth control so neither wore a condom.

Both indicated they were about to cum to I quickly stood them both up, I got on my knees and they both unloaded simultaneously on my face and in my mouth. I managed to swallow a fair bit.

Afterwards I went to the shower and checked my ass in the mirror, it was loose and gaping a little bit which I thought was kinda slutty :p.

When I came back Shaun had left and had told Dean to tell me to say thanks and that we should do it again sometime. We did it again a few times after until me and Dean broke up (:

Source: reddit.com/r/gonewildstories/comments/3q8ope/that_time_i_got_dpd_by_my_then_bf_and_his_best