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STORY TIME: I Was The MAN



So a few years ago I was in a Friends with Benefits situationship with a guy named Jason*. I have known Jason practically my whole adult-ish life. We met when we were in middle school and pretty much keep in touch regularly through Facebook and Instagram. I used to only see him when I went home for the holidays. One Christmas break my mother had gone to visit some of her friends up state for the weekend so I was bored home alone so I decided to text Jason and let him know I was home. We began flirting back and forth through text late into the evening. I eventually invited him over so we could mess around.

So around 9 o'clock he comes over, with drinks and some bud in his book bag, we smoke and drink a little. Soon the party moves upstairs to my bedroom were be start making out. Things are getting pretty steamy we strip each other completely naked and he slowly pulls away. 

"What's wrong?" I asked 

"Nothing... I was just thinking" He stammered out.

"About?" 

"Well.." He starts "I've know you for a really long time and I don't think that I could ever try this with anyone else."

"Uhm try what exactly?" I nervously asked.

"Well.." He clears his throat. "You know I watch a lot of porn and I've seen girls do anal and they seem to enjoy it. 

"You want to do anal? I thought you said it would be something wild!: I laughed.

"Well, I want you to do it to me..." He asked sheepishly

"Oh...OH!" I gasped

The room was like dead quiet. I just stared at him and he was looking down at the bed. 

"So are you gay? Or.." I asked 

"NO! No! no nothing like that, I'm just curious. Like they seem to enjoy it so I mean why not? 

Well a little bit about me is that this has always been a little bit of a fantasy for me. I've always wanted to dominate a guy in the worst way so of course I said...

"Well if it's something you wanted to try. I mean I guess I could try it too.." 

His face lit up because he opened up to me in the most honest way. I was happy too because I was able to finally live my dream. You might be wondering how we actually did this. Well there was more than booze in that back pack, there was a strap on. He had bought one a while ago but never used it. It was still in the original packaging and everything complete with lube. 

He bent over before me, booty perched and ready and I inserted it in. I never knew what kind of pleasure a strap on could bring but when I tell you I truly never felt more powerful in my entire LIFE it was amazing. Like I can't explain it, it was just amazing. The wincing, the squeezing, his slight moans. After about 3 minutes he was ready for it to be over.  Then we went on to the more traditional way of intercourse. 

The night ended with a hug and a kiss goodbye. I'm honestly surprised it wasn't a little more awkward than that. We talked for a few months after that and every now and again I'll see him on Facebook but we don't keep in touch as much now but it's nice to know I'll always be his first.

*Names have been changed.

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