Role swapping and ‘mutual anal'[MF]

I consider this the first time i get properly pegged because the girl was amazing and the dildo was a good size. I did it once before going after a craigslist ad but the woman was old, odd, and the dildo was tiny….so i went back to craigslist and to try again.

I found an ad posted the night before for a girl who was interested in “mutual anal”. I wrote to her interested what “mustual anal” meant. we start to text and it turns out she is addicted to anything anal but her boyfriend doen’t like anal at all she she is starving for some anal play. She likes to use a strap on and then get pounded in her asshole. I tell her about my past experience and how disapointed i was, she then tells me that she has a big cock for me to worship and will strech my asshole out. I boast the same, confident that my 7.5″ cock is bigger than what most girls allow near their assholes. We text like that all morning until I suggest we meet for a lunch fuck. She agrees and sends me the address.

I leave the office with a full hardon and driving to her house in full andicipation. I get to her house and eagerly knock on her door. She quickly lets me in and shuts the door behind me. We exchange some pleasantries and light conversation about weather and my drive over all while slowly making our way to the bedroom. It was the kind of conversation we both partook in because that was what was expected but we both knew neither of us really wanted to…it was just a way of getting comfortable with a stranger before getting naked.

When we got to the bedroom she stood in the door way and motioned for me to go in, but i decided to end the conversation and make the first move. I went into the door way put my hand on her side and leaned in to kiss her. She returned my kiss and i could feel her relaxing. She was letting go of her aprehension of me as the new stranger and we were finnally getting down to buisness. Sheryl was her name and she was a half white half black mix, she wasn’t too much shorter than me standing at about 5’10”. She had curly dark hair and a few extra pounds but she was well kept for sure. as we kissed we slowly walked towards the bed and were sheading clothes along the way. As soon as her bra came off she snapped into a different person, she gripped my hair pushed my head down then said “suck these tits like a good little boy” i looked up and sucked, licked and nibbled on her nipples as her head went back and she let out some groans.

with a smile she brought her head back and pushed me onto the bed and said “be right back, get ready to be streched”. excited i took off my pants and underwear and lay on the bed softly stroking my cock in anticipation. She comes back with a huge grin on her face, and a huge strap-on. This dildo was big, my cock is 7.5″ long and 5.2″ around, and this made my cock look small. it was probably 10 inches long and maybe 6 inches around. I looked up at her and said “you weren’t joking you have a big one, i looked down at my cock and said “and i thought mine was big” she said “honey, thats adorable….now lets get you bent over”

I bent over like a good boy but said “i don’t know if it’ll fit, i’ve never had anything that big” to that she replied by saying the same thing i just said but in an exagurated whiny voice. The humiliation she was giving me was really turning me on. I felt the cold lube hit my asshole jumped a little, she slapped my ass hard and said “you ain’t felt nothing yet” and then pushed a finger inside me, then two and she said “whats all this complaining you are taking these fingers like you are a little slut” she then put in a third finger which hurt a bit but she didn’t care, she was satisfied that i was able to take her by then so she took her fingers out, put some more lube on my ass then stood next to me lubing up the giant cock like she was jerking off…all while staring at me.

She took up her position and put the tip of the dildo at my ass and started to push. dispite what i was expecting she was very gentle…but firm. She pushed the cock in and out of my ass what probably was milimeter by milimeter but it felt like it was foot by foot. I shreaked and said painfully “i don’t thin it’ll fit…it is too big” she then just leaned forward, yanked my hair back and whispered in my ear “just relax, and breath” with that she gave it a big push and the dildo poped in my ass. it was painful and she saw it on my face and she said “stop acting like it hurts, didn’t you see how much your ass just swallows it up” let go of my hair and threw my face forward and started to to go to town on my asshole.

At first she just was trying to fit all of it inside me, pushing in it an inch deeper then pulling it out. Very quickly the pain went away and made way for the pleasure. She saw the point that my face loosened and my hands stopped gripping the sheets and she said “thats it, you love it now, what a faggot” and she then pushed the rest of the dildo into my ass. It felt weird but good and she was thrusting and slapping my ass with her thighs. She kept telling me how good my ass looked eating up her cock. I’m not sure if guys actually have anal orgasms but after a few minutes of her pounding the shit out of my ass i felt a buildup inside me and my ass convulsed, and i had similar feelings of an orgasm without the cum. I think she noticed this becuase she said “omg this is so hot, i’m dripping wet, take me now”…she slowly pulled the cock out of my ass and heald my ass cheeks open then said “mmmmm look at that gaping ass, what a stupid slut you are”

and as soon as she was out of my ass and she took the strap-on off she was a different person. Her body language was softer, she looked up at me with innocence in her eyes instead of lust and power that she had before. My cock was throbbing so i told her to flip over and put her ass in the air. her pussy was litterly dripping, i could see the drips that were running down her leg. I gathered her juices with my finger and used it to finger her asshole. Her asshole was very tight, and it took a little time for it to get my second and third finger in, but her ass accepted it.

I then took my my position next to her lubing up my cock staring at her while i did it. i asked “are you ready for a good fucking” With her cheek pressed against the sheets she just bit her lip and nodded.

I took my positoin behind her and circled my cock around her asshole before dipping it in. she was very tight still and my cock was not going in, so i tried to be gentle, easing it out then putting it back in with a little more pressure. I could see her closing her eyes and clutching the sheets. a situation i was in not 15 minutes ago. So i did what she did, I grabbed her by the hair, yanked her head back and whispered “remember, as you said….just relax and breeeaaath” and as i was saying breath i kept constant but increasing presure in her ass. She then let out a long breath and as she did my cock slid slowly into her asshole. She let out a little shreak of pleasure/pain so i slapped her ass hard and exclaimed “wow i knew you were a good slut…now push yourself and take the rest of my cock”

I stood still as she moved her body back and forth sliding my cock deeper and deeper. She was about half way down my cock when she started to move back and forth humping her ass on my cock. I think she thought she had taken my whole cock then because she started to get into it and then wound up for one good hump and she slammed her self onto the rest of my cock, let out a howl of pleasure and surprise.

After my initial pounding I was having trouble keeping my self calm. and her howl quickly pushed me closer to cumming. I put my feet in a squat, grabbed ahold of her neck from behind and started to pound her asshole with all the force i felt she pounded me with. She let out a moaning yell and i felt her ass gripping my cock more, her legs then gave way and she collapsed out from under me while she had her orgasm. I was very close to mine, and in my lust i didn’t let her finish her orgasm i just flipped her over to her back and put her knees to her ears and pounded her ass until i unleashed a huge load deep while i was deep inside her (wore a condom).

I pulled out of her and we lay there sweating and catching our breath. We then debated over who fucked who better or who was a better bitch, or who takes a cock like a better slut. we actually didn’t see eachother again, not because we didn’t want to but work and other things got in the way until maybe she found someone new.

Source: reddit.com/r/gonewildstories/comments/8vhzsa/role_swapping_and_mutual_analmf