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"Try to relax, this might hurt a little at first," she said.
She then positioned the head of the strap-on in front of my butthole and slowly began to put some pressure on it by thrusting her hips forward. As I felt it begin to enter my ass, I flinched and pulled away.
"We don't have to do this if you don't want to," she giggled.
"Can I fuck you instead?" I asked, hoping she might relent in the heat of the moment.
"No," she giggled again.
Clearly, she was enjoying the moment.
"Shall I continue?" she asked.
"Ok," I replied.
She then resumed pushing the head of the strap-on into me. It hurt as the head expanded my tight sphincter. After a minute, it felt like the head was completely inside of me and Allison paused for a moment to let me get use to that.
"You like that baby?" she asked as she gently rubbed my lower back.
"It hurts a little," I said.
"Arch your back and stick your butt out more," she replied.
I did as she told me and arched my back, sticking my butt out for her. Once I did, she gradually pushed the strap-on further into me.
"Ooooh," I groaned.
"Try to breathe and relax your muscles. It will hurt less" she said.
"Pull it out, pull it out, please, please," I whined.
"If I do, it's just going to hurt more when I put it back in again," she said as she leaned in and kissed the back of my neck.
I tried to relax myself and took deep breaths as she began thrusting into me a little deeper with each thrust. I winced a little. It really hurt and my ass felt like it was on fire. Sensing my discomfort, she held onto my hips and stopped thrusting for a moment.
"you're doing great." She said.
She then pulled most of the strap-on out, leaving only the head still inside me, then thrusted back into me. She did this a few more times, as I continued to wince in pain. She pushed one more time and buried her strap-on completely inside of me. She then stayed still, letting me get used to the sensation.
"Ooooh," I groaned as I grabbed her blanker with my hands and bent my head down.
"Are you ok?" she asked.
"It really hurts," I replied.
"Just be patient, you'll get used to it," she replied as she continued slowly thrusting.
I then reached my hand and started stroking my rock-hard erection.
"Uh uh uh, "she said as she reached down and swatted my hand away.
"Why not?" I asked.
"According to an article I read, you should be able to cum hands free," she said.
"I don't know if that's possible," I replied.
"Supposedly, the head of the strap-on should stimulate your prostate and you should start to feel good," she said.
"I don't know," I replied with a hint of skepticism in my voice.
"You can do it," she said as she resumed thrusting in and out of me.
My cock was rock hard by this point.
"Fuck," I whispered.
"Just give it a few more minutes. You're doing so well," she said, trying to reassure me.
"Ok," I replied.
"How does it feel to be on the receiving end?" she asked.
"Different," I replied.
"I imagine it does," she giggled.
"Have you ever had a strap-on up your ass?" I asked.
"Nope. Though I have fucked some of my girlfriends up the ass," she replied.
The thought of that made my erection grow a little more. As she continued thrusting, I could feel the head of the strap-on rub against what I assumed was my prostate and it started to feel good.
"How does it feel?" she asked.
"Better," I replied.
For the next few minutes, we didn't exchange any words; each us simply lost in the moment as she continued to thrust in and out of me. Suddenly, I felt an orgasm beginning to build.
"I think I'm gonna cum," I said.
"Cum for me, baby," she whispered.
As she continued thrusting into me, I resisted the urge to reach down and stroke my own cock.
Suddenly, without warning, I began to cum. My whole body spasmed while Allison continued to fuck me even as I came; shooting huge sheets of cum across her blanket.
After I came, Allison stayed still for a few moments with the strap-on still deep inside of me. Gradually my cock slowly went limp.
"That was hot!" she said.
"Can you please pull it out," I whispered.
"Oh, sorry," she giggled as she slowly withdrew the strap-on from my ass. I immediately felt a feeling of emptiness.
"I can't believe I came so hard!" I said as I rolled over to face her.
"I told you your body can get use to anything," she said with a smirk.
- COMMENTS
Anonymous8 months agoTouched a few nerves here didn’t you (pardon the pun). Moral indignation from the lesbian side about men not believing that attractive women can be lesbian. Annoyance from the pedants about freedom of speech and not being allowed to comment on stories you don’t like. Self righteous nonsense from the bi-curious men, pretending they enjoyed being pegged. Mix in a little misandrist hot sauce and you’ve pretty much covered all the bases. Oh sorry, add the “All men are bastards” line and you have a full house.
Samantha4198011 months agowhy is it weird that a lesbian would be attractive? and whey do guys think a lesbian wants to have sex with them. Lesbians want to have sex with a guy as much as straight men want to have sex with a guy.
Anonymousalmost 3 years agoI clearly remember the first time I was on the receiving end. We'd talked about it earlier so I knew what was coming. Unlike the story, she spent a lot of time stretching me out and lubing me up. One finger, then two, and finally three. Her "cock" slipped right in. It did hurt a little but not for long. It didn't take long to get to "pegging heaven"
