Anyway, here it is!
The Gift of a Lifetime
I know it's kind of a cliche, but sex changes everything. After Amy and I were together for that first time, it was like a whole new world opened up to us. Or to her. Everything was usually her idea. I'm not exactly assertive, so I just went with the flow. She wanted to try new positions, so I did. She wanted to be naughty in public places, so we were. She was so adventurous.
I remember thinking that maybe she was searching for something. Was she dissatisfied with my performance, such as it was? Or was she just kinky? Of course, the thoughts ran over and over in my head; that's just the type of person I am. I worry. A lot.
Anyway, I guess one day, Amy was feeling particularly frisky when she was going down on me. She took my entire penis and my testicles into her mouth (with room to spare, no doubt). And then I felt her finger slip into my anus. I flinched. i couldn't help it. I mean, it's not something you expect, is it? But like I said, I wasn't in the habit of saying no to any of Amy's sexual experiments, so I forced myself to relax as she worked her finger in and out. All the while, she kept me in her mouth, tonguing and sucking. Once the intial shock of being penetrated wore off, I sort of lost myself in the feel of it all.
I had never felt anything like it before. It wasn't so much the pleasure of it (though there was plenty of that). It was the feeling, the idea of it. I felt naughty. I felt submissive. I was in her hands. And I liked it.
After I came, Amy sat beside me, stroking my hair. "I guess you liked that, huh?" she asked with a knowing smile. I could only smile in response. After that, whenever Amy went down on me, she'd have at least one finger inside of me. Sometimes, she didn't even bother with my penis, and just concentrated on my anus.
I don't know why, but I was always more comfortable when she neglected my penis. Sure, it didn't feel quite as good (though it came close), but...I don't know. The best I can describe it is that it felt right.
I don't know if that makes me strange. Maybe all guys would like it if they gave it a chance. Or maybe not. I don't know, and quite frankly, I don't care anymore. Maybe Amy's adventurous spirit is becoming infectious. Maybe it's rubbing off on me.
So where was I? Oh, yeah. Our sex life took a bit of a strange turn on Valentine's Day that year. We had just been on a wonderful date -- Amy took me to a very expensive restaurant -- and we were in her dorm room. Her roommate, as usual, was out.
"I got you a present," she said.
I didn't know how to respond.
"I know we agreed not to do presents this year, but, well this one is kind of for both of us. So I figured it would be okay," Amy said, handing me a box. "Go ahead. Open it."
I unwrapped it, and then opened the box. What I saw when I opened it was a little disconcerting.
"I know how much you, um, like it when I put my fingers in there. So I thought we'd go for something a little more...stimulating," she explained nervously.
I knew the look on my face was one of shock. I mean, what other expression is there when your girlfriend gives you a strap-on dildo for Valentine's Day? I don't care how adventurous or open your sex life is, it's still bound to elicit a few strange thoughts.
"If you don't like it, we don't have to --"
Her tone broke me free of my shock. It was so weird to hear embarrassment in her voice. She was always so confident, so strong. And here she was on the verge of tears, and it was because of me.
"N-no, it's not that. I, um...I was just surprised is all," I said in as comforting a voice as I could muster.
She perked up. "So you really like it?"
"I don't know. I'm willing to give it a shot, though."
"Oh, you'll love it. I'm sure of it!"
And she launched herself at me, hugging me tight. The hug became a kiss, and the kiss...well, it wasn't long before we were both naked.
She reached for the box.
"Oh...you want to do it now?" I asked tentatively.
She shrugged. "Why not?"
I don't know why I was so hesitant. It wasn't like I hadn't had anything in there before. What was the big deal? Or at least that's what I told myself. But I knew, even if I couldn't admit it to myself. There's quite a big difference between a finger and a strap-on dildo.
What was I supposed to do, though? She plainly wanted to use it, and I couldn't really deny her that pleasure.
"If you want to," I said.
She was so excited -- like a kid on Christmas morning. -- as she strapped the harness on. When she was finished, she said, "Come here." I did. She grabbed my hand -- it was so tiny next to hers -- and she placed it on the rubber dildo. It was so realistic. It had veins and everything. And it was big, so much bigger than her finger. So much bigger than my own member. She guided my hand up and down its shaft.
From somewhere, she produced a tube of lubricant, and squirted some onto my hand. I continued to massage the dildo, making it slippery. I knew the time was close, and I was so nervous. Would it hurt? What if I liked it? What if I didn't? What if it was some sort of test? So many thoughts raced through my head, but all the while, I stroked my girlfriends brand new cock.
Amy put her hand on my chin, and lifted my face to hers. She leaned down and kissed me gently. Our eyes locked. It was time.
I was in a bit of a daze as I got on all fours on her bed. I buried my face in her sheets, arched my back, and raised my butt into the air.
I felt Amy's finger at the entrance to my anus, and I flinched a bit. She patted my butt, and cooed, "Relax, baby." Her finger slipped in, the lube coating my insides. I pushed back against her hand, it felt so good. But she pulled her finger out, and I sat there, my heart beating a hundred miles per hour in anticipation.
And finally, I felt the tip of the dildo on my rectum. Slowly, gently, Amy pushed it inside. And it hurt. Bad. It felt like I was going to split in two. I wanted to tell her to stop. I wanted to pull away, but something wouldn't let me. Inch by inch, it went in, until, finally, I felt her hips against my upper thighs. She was in all the way. We stayed like that for a few seconds. I don't know why. Maybe Amy wanted to let me get acclimated to having it inside of me. But it felt like an eternity before she started to pull out.
By the time she had pulled out, the pain had subsided a bit. It still hurt, but not nearly as badly. And then she was pushing back in, a little faster this time. And then back out. By the time she had built into a steady rhythm, the pain was gone. In its place was pleasure, pure and simple.
The way she slammed into me, in and out so furiously, it was a revelation. I couldn't help but moan. I even let out a few muffled screams.
In hindsight, I know they sounded very girlish. My voice had never really changed all that much.
But the sheer physical pleasure of it wasn't the best part. No, what really hit me was the fact that, for once, my mind was clear. I wasn't thinking about any of my thousands of worries. I wasn't fretting over what Amy thought of my tiny penis. I was lost in the act.
We went on for what seemed like hours. I'm not ashamed to say that I walked a little funny that next day. But I know I was glowing. I know that I felt better than I ever had in my entire life.
For once, my happiness wasn't qualified by some addendum. It wasn't a footnote. It was absolute.
If only it could have lasted.
I remember thinking that maybe she was searching for something. Was she dissatisfied with my performance, such as it was? Or was she just kinky? Of course, the thoughts ran over and over in my head; that's just the type of person I am. I worry. A lot.
Anyway, I guess one day, Amy was feeling particularly frisky when she was going down on me. She took my entire penis and my testicles into her mouth (with room to spare, no doubt). And then I felt her finger slip into my anus. I flinched. i couldn't help it. I mean, it's not something you expect, is it? But like I said, I wasn't in the habit of saying no to any of Amy's sexual experiments, so I forced myself to relax as she worked her finger in and out. All the while, she kept me in her mouth, tonguing and sucking. Once the intial shock of being penetrated wore off, I sort of lost myself in the feel of it all.
I had never felt anything like it before. It wasn't so much the pleasure of it (though there was plenty of that). It was the feeling, the idea of it. I felt naughty. I felt submissive. I was in her hands. And I liked it.
After I came, Amy sat beside me, stroking my hair. "I guess you liked that, huh?" she asked with a knowing smile. I could only smile in response. After that, whenever Amy went down on me, she'd have at least one finger inside of me. Sometimes, she didn't even bother with my penis, and just concentrated on my anus.
I don't know why, but I was always more comfortable when she neglected my penis. Sure, it didn't feel quite as good (though it came close), but...I don't know. The best I can describe it is that it felt right.
I don't know if that makes me strange. Maybe all guys would like it if they gave it a chance. Or maybe not. I don't know, and quite frankly, I don't care anymore. Maybe Amy's adventurous spirit is becoming infectious. Maybe it's rubbing off on me.
So where was I? Oh, yeah. Our sex life took a bit of a strange turn on Valentine's Day that year. We had just been on a wonderful date -- Amy took me to a very expensive restaurant -- and we were in her dorm room. Her roommate, as usual, was out.
"I got you a present," she said.
I didn't know how to respond.
"I know we agreed not to do presents this year, but, well this one is kind of for both of us. So I figured it would be okay," Amy said, handing me a box. "Go ahead. Open it."
I unwrapped it, and then opened the box. What I saw when I opened it was a little disconcerting.
"I know how much you, um, like it when I put my fingers in there. So I thought we'd go for something a little more...stimulating," she explained nervously.
I knew the look on my face was one of shock. I mean, what other expression is there when your girlfriend gives you a strap-on dildo for Valentine's Day? I don't care how adventurous or open your sex life is, it's still bound to elicit a few strange thoughts.
"If you don't like it, we don't have to --"
Her tone broke me free of my shock. It was so weird to hear embarrassment in her voice. She was always so confident, so strong. And here she was on the verge of tears, and it was because of me.
"N-no, it's not that. I, um...I was just surprised is all," I said in as comforting a voice as I could muster.
She perked up. "So you really like it?"
"I don't know. I'm willing to give it a shot, though."
"Oh, you'll love it. I'm sure of it!"
And she launched herself at me, hugging me tight. The hug became a kiss, and the kiss...well, it wasn't long before we were both naked.
She reached for the box.
"Oh...you want to do it now?" I asked tentatively.
She shrugged. "Why not?"
I don't know why I was so hesitant. It wasn't like I hadn't had anything in there before. What was the big deal? Or at least that's what I told myself. But I knew, even if I couldn't admit it to myself. There's quite a big difference between a finger and a strap-on dildo.
What was I supposed to do, though? She plainly wanted to use it, and I couldn't really deny her that pleasure.
"If you want to," I said.
She was so excited -- like a kid on Christmas morning. -- as she strapped the harness on. When she was finished, she said, "Come here." I did. She grabbed my hand -- it was so tiny next to hers -- and she placed it on the rubber dildo. It was so realistic. It had veins and everything. And it was big, so much bigger than her finger. So much bigger than my own member. She guided my hand up and down its shaft.
From somewhere, she produced a tube of lubricant, and squirted some onto my hand. I continued to massage the dildo, making it slippery. I knew the time was close, and I was so nervous. Would it hurt? What if I liked it? What if I didn't? What if it was some sort of test? So many thoughts raced through my head, but all the while, I stroked my girlfriends brand new cock.
Amy put her hand on my chin, and lifted my face to hers. She leaned down and kissed me gently. Our eyes locked. It was time.
I was in a bit of a daze as I got on all fours on her bed. I buried my face in her sheets, arched my back, and raised my butt into the air.
I felt Amy's finger at the entrance to my anus, and I flinched a bit. She patted my butt, and cooed, "Relax, baby." Her finger slipped in, the lube coating my insides. I pushed back against her hand, it felt so good. But she pulled her finger out, and I sat there, my heart beating a hundred miles per hour in anticipation.
And finally, I felt the tip of the dildo on my rectum. Slowly, gently, Amy pushed it inside. And it hurt. Bad. It felt like I was going to split in two. I wanted to tell her to stop. I wanted to pull away, but something wouldn't let me. Inch by inch, it went in, until, finally, I felt her hips against my upper thighs. She was in all the way. We stayed like that for a few seconds. I don't know why. Maybe Amy wanted to let me get acclimated to having it inside of me. But it felt like an eternity before she started to pull out.
By the time she had pulled out, the pain had subsided a bit. It still hurt, but not nearly as badly. And then she was pushing back in, a little faster this time. And then back out. By the time she had built into a steady rhythm, the pain was gone. In its place was pleasure, pure and simple.
The way she slammed into me, in and out so furiously, it was a revelation. I couldn't help but moan. I even let out a few muffled screams.
In hindsight, I know they sounded very girlish. My voice had never really changed all that much.
But the sheer physical pleasure of it wasn't the best part. No, what really hit me was the fact that, for once, my mind was clear. I wasn't thinking about any of my thousands of worries. I wasn't fretting over what Amy thought of my tiny penis. I was lost in the act.
We went on for what seemed like hours. I'm not ashamed to say that I walked a little funny that next day. But I know I was glowing. I know that I felt better than I ever had in my entire life.
For once, my happiness wasn't qualified by some addendum. It wasn't a footnote. It was absolute.
If only it could have lasted.
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