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After a date night with lots of talk about ass play, our main character gets excited about a sexy surprise his girlfriend has in store for him. He anticipates being able to have anal for the first time with her but then the tables are turned and he learns about the pleasure of pegging…

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Transcript

I loved Thursday date night. Each week, one of us would choose either an activity and restaurant so that we could continue to try new, fun things together. Usually, that also meant we would fuck like animals when we came back, becoming newly attracted to one another again. Brianna was a super relaxed surfer girl type from California who came to London working for a tech company. I was your typical British dude who loved to watch the footy in a pub when it was raining outside. Sometimes I don’t even know how we work, we are both so opposite, but I guess that adds to the newness of our relationship, we’re always exploring each other’s view of the world.

I planned date night this week and we had an incredible time at a new play in the Westend and then a delicious dinner at a nearby Sri Lankan place in Soho. We continued our night by going to a wine bar with a speak-easy on the corner and listened to jazz music as we drank our Muscadet. It was bloody romantic, even I was feeling ultra-connected to Brianna. We drank more wine than we should on a weekday and might have made out like teenagers at the wine bar.

We had discussed a lot of things, including sexual fantasies. Both Brianna and I were pretty open in the bedroom, but she had expressed to me early on that she wasn’t a big fan of anal. Which was totally fine, we all have our boundaries. We had fiddled around with toys on me before and I loved prostate play. It was naughty in a society that was so uptight, so I knew that lots of British men were secretly, deeply pleasured by it.

Our conversation turned to this subject and Brianna cryptically said that she was keen to spice things up by trying some new bum fun. She didn’t tell me exactly when she meant by it but damn, I was excited either way. This morning when I wake up, there's a note on my nightstand. It's from my Brianna, who went to work early, it read, "tonight, it will be you, me, and a bit of butt play”. I raise my eyebrow and decide not to wank off in the shower today, I’ll save myself for Brianna and her lovely ass, later.

I try and focus on work, but I can feel my mind flitting between actual work and thinking of the incredible time Brianna and I will be having later, I try and keep sat at my desk as I keep getting hard. I get home earlier than she does and start preparing dinner.  

Brianna comes home and tells me about her long day, while I’m setting the table. I pour her a glass of wine and she relaxes, finally out of work mode. By the time dinner is ready and she has a certain twinkle in her eyes. At the end of the meal, she has turned on her sexual prowess and asserts herself,  

I’m going to go upstairs to refresh myself. When I call for you, you come upstairs. Immediately," she tells me with a strict, but cheerful undertone in her voice. I’m surprised at her metaphorically cracking the whip, she’s usually so laid back and go with the flow, this is a huge character change for her, but I kind of like it. I sit, patiently waiting, like I was told, until after about fifteen minutes when I hear her voice calling me. I proceed upstairs, excited.

 In our room, she stands in dark blue lace lingerie with open crotch panties. But it's not her pussy that the panties reveal. It's a feeldoe, strap on that is held in place in her vagina that is able to stimulate her whilst she’s using it.  "Come over here babe", she says. I tentatively walk over and she pushes me down onto the bed. "When I said anal was involved, I didn't point out who would be on the receiving end", she smiles.

 I look her up and down, admiring her lush figure and my eyes halt at the feeldoe. I can feel my heart racing, pounding in my chest. I’m full of so many different emotions. On one hand I’m extremely turned on by my sexy partner and the way she is controlling the situation. On the other, I’m still trying to process that the feeldoe is going up MY ass, it was not what I was expecting at all. But I decide to let the first feeling overtake me and I can feel the blood pulsing through my cock.  

Brianna climbs on top of me and pins my arms down with her legs. Her beautiful bottom is right in front of my face. When she bends over to jerk my cock, I can see the feeldoe pointing towards her lace encapsuled breasts. I can tell that her pussy is wet, and the juices are glistening around her cock, while she jerks mine. I give a low gruff moan, melting into the pleasure of her hand wrapped around my hardness.

Brianna starts to whisper into my ear, "I know you crave this, being pegged under my control." I have never experienced this dominant side of her and it’s one of the hottest things I’ve ever experienced. She takes her hand off my cock momentarily and drips some lube onto her fingers. I feel the coolness of it as her hand makes he way down to her "Tonight, I’ going to make you mine” she tells me while a fingers slides inside and touches my prostate. I gasp, feeling the pleasure slide up my back to my brain.

Brianna smiles at me and lowers her body so that her mouth wraps around my shaft and she slowly moving my cock up and down her throat. It’s almost too much to bear and I feel my orgasm coming closer. She senses then and then I feel the weight lifting from my arms, as she stands up. She looks at me, with an eyebrow raised and then spreads my legs, and playfully wraps her hand around my balls. "Ready?", she asks. I nod and after a few seconds I can feel the head of the feeldoe sliding in. A rush of arousal comes over me. Never had I thought that she would take the reins like this, pleasure me like this.

There’s a bit of pain at first but then my asshole relaxes and I’m able to enjoy the touch of pain with pleasure. Brianna is masterfully, rhythmically thrusting into her and I enjoy physically feeling her power. She groans as the feeldoe hits her g-spot and I know she’s enjoying this as much as me. Brianna is one of the lucky women who can cum from internal stimulation.

She reaches down and grab my cock, rubbing it as she continues to penetrate me. I meet her eyes with mine and see her mouth opening, she’s about to cum and I too cannot hold it in any longer. I feel closer to her than every before. Then I hear her scream and it send me over the edge and, with my cock pointed to her chest, I release my cum all over her breasts and quake with the incredible pleasure of an anal orgasm, my ass gripping tight around the feeldoe as I finish.

Brianna is panting and looks down at herself, covered in my white, sticky, liquid and she laughs, telling me she couldn’t wait to do it again.