This happened when I was 22 and had been out of work for a bit. It led to me having a place to myself for hours and hours. And boy did I take advantage of it!
At the time I was hooking up with a bunch of different guys and each of them for a different reason. One loved coming over just to get a blow job and play with my breasts. He always offered money and looking back I was stupid to have turned it down. Another had a less than average penis. He was constant pressure on my g spot. A different guy was a college freshman who had a habit of cumming in his undies before we got started. My first anal though? He was a somewhat nervous man on his lunch break.
I had hopped on my bed and slid my underwear off, always eager to be filled. This man who would soon become forever imprinted in my memory slowly removed his suit and tried to make small talk.
He asked, “Have you done anything like this before?” And I paused for a bit. Debating if I should pretend to be a newbie as he clearly was or let him know he was dealing with someone with an insatiable craving. I nodded my head in the affirmative.
That ended the small talk. I was a bit worried he’d seen me as disgusting or something. But then he removed his pants and revealed a larger than average hard on. He hurriedly joined me in bed then his hand immediately diving to my clit as my hand grabbed a hold of him. Our lips met softly as our hands were more rough on each other’s lower parts. I was so wet. I needed more than a jelly bean and finger play date. And as if he read my thoughts he grabbed a condom.
At first our lower halves met like at the junction to a “T.” He was vertical and on his side facing me. I was horizontal and on my back with my knees close together. This, I had learned from my less than average playmate, made me feel tighter. And I devilishly squeezed my vagina each time our hips parted. A vise grip almost as to keep him from leaving me empty. Only it worked a bit to well. He excused himself for a bit and went to the end of the bed to calm down.
Now I’m never one to stare down anyone’s awkward moments or rush them along. Quite the opposite. So I stole his previous spot, rolled over onto my belly, and kicked my legs back and forth to wait for him. I suppose this must have been an enticing sight for him as not a minute later he blanketed my body and slid back into my warm and wet hole.
The submissive in me loved being in such a position where he had complete control. I could only slightly raise my hips to better offer myself to him before his body weight reminded me I could do no more. And that he had pounced on me suddenly as though I were prey? I had never been so turned on in my life. But not a few minutes later he would raise the bar again.
Once more he retreated without returning. I assumed it was another cool down moment or that he had orgasmed. But then there was a steady and firm pressure in between my bottom cheeks. I came as soon as he was in to his hilt. With no lube but my wetness he gave me long and measured strokes as I mewled underneath him. The slight pain, the feeling of being driven to another orgasm, and just the taboo of it had driven me out of my mind with pleasure. When he came I greedily wished he hadn’t yet. I wished that he would have stayed there for hours with his long and steady strokes which had brought me euphoria and the slight sting of pain that I so enjoy. But it was over.
As he dressed I sat on me bed watching him. My back hole felt so loose. A reminder of what had happened. Of what I had just done for the first time. He periodically would come kiss my neck. Getting me turned on again with no hope of release from him. I gave him my contact information and soon enough he was in his suit and gone forever.
He did contact me again but we never hooked up again. As great as the experience was I definitely feel as though carrying on with him might encourage surprise anal with other women he might hook up with. Especially if I told him that was my favorite part.
Source: reddit.com/r/gonewildstories/comments/9ajzh4/mf_my_first_anal
Wow! Hot! Do you know how old he was?