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Why I Agreed to Be a Bend-Over Boyfriend *LINK*

Throwing caution and societal expectations to the wind, I let my girlfriend screw me for a change

The first time my girlfriend fucked me in the ass it was with a small purple strap-on dildo that her ex-girlfriend had shipped from Ohio. Like any lady should before taking her man's anal virginity, my girlfriend took me for a night on the town beforehand. Walking home, after dinner and a long stop at a bar, we decided it was about time I made good on an earlier promise to let her screw me for a change.

Butt sex wasn't my idea. As far as anal is concerned, I'm not exactly a connoisseur. That goes for giving as well as receiving. Aside from a female college friend turned one night stand who demanded it and the occasional forefinger while I'm going down on a woman I haven't thrown much up anybody's (to quote a friend back in junior high) dirt spider. And, aside from receiving the occasional stinky pinky while a girl went down on me, not much had been up mine.

That all changed when I met Mac. Not right off the bat, of course. Our first date, scheduled a few months after meeting through mutual friends, started off as American as apple pie. We met near her downtown office after she clocked out of her 9 to 5 and I took her to her second-ever baseball game. The San Francisco Giants were facing off against Texas. The sun was setting over the bay. We had hot dogs, popcorn, and cold lemonades. American. Ok, the lemonades were spiked with rum. But the rum was from a bottle I had smuggled into the stadium in my left cowboy boot, so the theme still fits. It was probably the most wholesome date I had been on all year.

Toward the end of the game Mac brought up that she had a girlfriend. I'd been living in San Francisco for more than a year, so I tried to hide my disappointment and act like girls brought that up on first dates all the time. Mac quickly made it clear that she was in an open relationship with her girlfriend, who actually lived in Ohio. Emboldened by that information, the cowboy boot rum, and the fact that I had already fallen in love with her in the 5th inning I decided not to let a girlfriend deter my efforts. Mac did the same; after the game we ended up in bed.

It was early on in our relationship when Mac asked if I would let her fuck me in the ass with a strap-on, and I was drunk. But that wasn't the reason I agreed to her proposition. Neither was the fact that we seemed to be half joking at the time. I was curious, but that wasn't it either. I've been curious about more than a few things that I've never actually gotten around to doing. As for it being the first step on a closeted path of desire toward experimenting with men, that just wasn't the case. Same goes for repressed fetishes: Being fucked in the ass was never on my list of secret dirty wishes.

But Mac had been sleeping with women since high school and she and her ex-girlfriends had screwed each other with strap-ons. I thought, given that she asked me about it, she might miss giving someone the business. Mac is a beautiful, intelligent, and supportive woman. I was head over heels for her, and I wanted to make her happy. I thought that along with pretty flowers and little cupcakes, letting her fuck me in the brown eye would be a way to show my appreciation for her. Ignoring the fact that societal standards don't exactly align with a straight male taking it up the ass, I agreed to let her nail me. Besides, I got to fuck her all the time; it only seemed fair.

Trying to be the world's best boyfriend wasn't my only motive. I also was in some weird competition with her exes in my mind. Mac had been able to fuck her incredibly butch ex-girlfriends with a strap-on, so why not me? Sure, they didn't take it up the ass, but I don't have a vagina so my options seemed limited. If those ladies were man enough to get fucked by Mac wearing a strap-on, then so was I.

Or so I thought. After I surprised Mac by agreeing to take it in the ass she asked her now ex-girlfriend, who apparently wasn't as open to their open relationship clause as she had let on, to be sure to send her dildo and harness along with the other personal items she was shipping from Ohio. All of this was new to me, so I was a little nervous. But after the strap-on arrived in its small Fed Ex box I was feeling more confident. It was not big. A few straps, a few metal rings, and a veiny, purple, dick-shaped piece of plastic about the size of two fingers. Taking that thing up the ass, it seemed, would be a cake walk.

We hadn't planned it the night it happened. "Take a dildo in the back door" wasn't written on my calendar. A few weeks had passed since the literal and figurative package had arrived and we were joking about it while eating dinner by candlelight. After some ravioli, a bottle of wine and heavy drinking at a bar near Mac's house, the joking took a serious turn. We had been bantering about our butt sex pact with a friend of mine that we had run into at the bar after dinner. The guy was laughing hysterically. But he also kept looking at me as if to ask, "Are you serious?"

And that's when it dawned on me. I was serious. I was going to do it. At that point it seemed clear to both of us that that night was the night. We excused ourselves and rambled home. Soon I found myself bent over on Mac's bed, my chest pushed up against the mattress, while she strapped the harness around her long legs and smooth hips.When she penetrated me for the first time I tensed up and let out a long succession of soft, high-pitched "ow"s. I was not off to a manly start.

"Are you ok baby?" she whispered. The strap-on was inside me but she wasn't thrusting. Instead she was leaning over me, her weight on my back as her fingers petted my face.

"I'm fine," I lied.

Mac knew I was bullshitting. Her movements were gentle and deliberate as she started to slowly rock against me. My ows dissolved into whimpering.

"Shhhh," she hushed, kissing my back, "you're doing such a good job."

But I wasn't doing a good job, and I knew it. The room seemed tight and close, and what I had thought of as a small piece of purple plastic now seemed large, long, and incredibly hard.

"More lube," I gasped.

It seemed to be the only words I could string together. That and "it hurts." When after a few minutes of extremely placid and unexciting anal sex, I said the former for about the fifteenth time, Mac stopped her slow thrusting.

"There is no more lube."I looked over my shoulder and she held up the empty container. She had been lubing me every time I asked for it and we had gone through four ounces in five minutes. She leaned over me and gripped hard on my hip in order to distract me as she pulled out. I gasped again and rolled over on my side, too drunk and worn out to stay awake.

The next day my ass didn't hurt like all holy hell to my surprise, although I did notice an awkward feeling while sitting and I walked a little bow-legged. I definitely didn't feel like any less of a man for having been penetrated. But I did feel like I had been a letdown. I was worried that I made a bad partner when I was the one getting fucked. I eventually found out that my performance was on par with an ex-girlfriend whose virginity Mac had taken, but that was months later. At the time I just felt like a punk who couldn't handle getting railed.

A month later I decided we should try it again. We were lying in Mac's bed after a bout of Sunday afternoon non-strap-on sex when I asked if she was interested in doing me in the butt. Mac hadn't asked to screw me since the first incident and I thought the reason she was no longer interested in getting down with my bottom was my poor performance. I wanted to make up for what a baby I had been. This time, I was determined to let my girlfriend do me up the ass right.

I got up on all fours while Mac kneeled beside me and strapped on her extremely out of place plastic penis. The room felt open in the afternoon sunlight. "You ready baby?" Mac was rubbing the strap-on up and down, as if she were giving herself a hand job. Although we hadn't discussed butt sex since the first time, it seemed that she had been thinking about it. In her right hand she held an expensive-looking glass bottle, one that I would have thought contained perfume if I had come across it in a department store, as she lubed up with her left. Mac leaned over and squirted the lube on my ass. The bottle was full and much larger then our last one. Written in script lettering was the single word "Pink."

"You couldn't find a manlier-sounding brand?" I asked. She smiled and climbed behind me.

My bravado lost its footing at first. The initial pain was still sharp and I started whimpering immediately. I focused on not tensing up as Mac eased further inside me.

"More lube," I muttered. I don't know much about lube, but Pink certainly gets my seal of approval. The painful friction seemed to lessen. I started rocking back into Mac.

"Fuck," she whispered. She picked up the pace, thrusting into me as I came up to meet her. My whimpering was replaced with gasps and cursing.

After a few minutes, Mac slid her left hand around my waist and started to jerk me off. It caught me by surprise. Reach-arounds were things I had joked about in high school, but now I didn't feel like laughing. I was getting a reach-around with my girlfriend's no-longer-thought-of-as-little purple dildo in my ass, and it felt incredible.

She became less gentle. She gripped my side with her right hand as we moved back and forth. I looked over my shoulder and she was smiling, sweating, and gorgeous as she repeated over and over what a good job I was doing. She rubbed my dick as we moved faster. I exploded all over the bed sheets, and we collapsed.

It's been five months, and despite that afternoon's success Mac hasn't mounted me from behind since. She enjoys it, but points out that given her penis is a piece of plastic strapped to her crotch, it doesn't exactly overwhelm her with physical sensations. While the same definitely isn't true for me (I certainly have physical sensations), getting fucked in the ass is still not my favorite sex act. It's one that I'm down with, but not one that I find myself pining for.

Friends find it interesting that I, a straight male, agreed to take it up the ass not once but twice, and would willingly do so again. My immigrant grandfather thought that clearing the dinner table was a womanly act. I reason that since I clear the table and do the dishes, getting fucked by a woman wearing a strap-on doesn't rob me of my manhood either. For me it wasn't a sexual orientation thing, or a power thing: It was just a sex thing. And if Mac feels like sliding her long legs into that harness tonight, I'll be more than happy to get on all fours and take it in the ass like a man.

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