Amazon Pegging

This story was originally written for theApril Fools 2026contest.

I am also working on The Survivor Project this year and not only am I trying to write in every category, but I have added the extra challenge of trying to include the same character, Randall, in at least one story in each category. Wish me luck.

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Amazon Pegging

Amazon Pegging

My older lover ties me up for an Amazon fuck, with pegging.

My older lover ties me up for an Amazon fuck, with pegging.

It started just after an early Saturday morning romp with my sexy older lover, Margot. "Randall? Do you trust me?"

Still catching my breath I turned my head and looked at her, "What? That is an odd question." We were both naked, although she had pulled the sheet up to cover herself somewhat. Just to stay warm, though, she was certainly not afraid of letting me see her naked. That was how we had met, after all.

"Do you?" She looked like she was serious, like she didn't know for certain.

"Of course I trust you! Why do you ask?" I rolled onto my side and stared into her eyes, searching for understanding.

"I want to do something to you. With you. But you would have to trust me." She reached out and touched my face.

"What do you want to do?"

She let out a deep breath that I don't think she realized that she had been holding, "I want to tie you up and fuck you."

I raised my eyebrows and asked, "And how is that different from our normal sex?"

"I've been talking to a friend about how she fucks her younger man. He lets her push his legs up to his chest and then she mounts him. It's called Amazon position, I think."

I laughed, "I know what you mean. I've seen videos. I'm not sure if I'm flexible enough, though. We should check it out, first. Maybe right now?"

Margot grinned at me. She knew I was just looking for an excuse to get inside her luscious pussy again. "Horny fucker! Ok, let's test you out."

Margot had a padded hope chest at the end of her bed. Normally I just left my clothes there when I stayed over, or even when I visited for a quickie, but she had me pull it away from the bed a little as she moved our clothes.

I sat on the end of the chest and Margot stepped between my legs; she bent over enough to kiss me deeply. Her large boobs sagged down a little and swayed back and forth as my tongue chased hers in and out of our mouths. She always smelled slightly of vanilla, even though she now also smelled like our sex from last night and this morning.

Rubbing my hands across her back and ass was nice. Margot was very physically active, she did aerobics classes and played tennis regularly and I loved the feel of her strong tone muscles. The feel of her skin was also very erotic, even though it wasn't as smooth and pliant as that of women my own age. It felt more like soft paper due to all the time she had spent in the sun. The tan lines of her bathing suits were visible even though she sometimes enjoyed nude sunbathing in her back yard. Her breasts, ass and pussy were tan, although not nearly as sun darkened as the rest of her body.

Margot pushed me back onto the hope chest and it was almost too short. I had to adjust to keep my head on a corner while my ass was on the diagonal opposite corner. Lifting my legs I held them behind the knees which left me spread wide open for her. To be honest I felt surprisingly vulnerable as she leaned over to cup my balls and stroke my dick to full hardness.

Taking my dick into her mouth freed her right hand and for the first time in the months since we met she also ran a finger across my asshole. I jumped at the sudden contact and she let my dick fall out of her mouth.

"And if you let me play with this I'll let you do the same to me afterward."

I didn't want to agree to anything while my little head was in charge, so I said, "I'll think about it."

Margot smiled as she walked up over me and held my dick pointing straight up. "I've never let anyone do me in the back before. You would be my first." She swiped me against her sex a couple of times and then stretched up before dropping down to take me inside.

Sighing, she slowly lowered herself onto me with short bouncing strokes. Once she had me all the way in she grabbed hold of my feet for support and started raising and falling onto me. The feeling was new, feeling her thighs on the outside of mine as she fucked up and down. Having my legs raised up meant I couldn't thrust as much as I normally would, but I did my best to meet her movements.

After about five minutes with her legs spread wide across me she looked down and said, "This is harder than it looks! Let's try the other way." Withdrawing herself she turned around and backed up over me. I saw her smile at me from between her legs as she seated herself and started twerking up and down. Holy shit, it was so good.

Margot thought so, too, since she moaned out loud, "Oh, this is so good!"

I watched her ass bounce up and down on me and was able to watch her little brown asshole twitch and move with each thrust. I'm sure she wasn't doing it on purpose, but my little head started taking over. I wanted to come, and I wanted to fuck her in the ass. She was leaned forward partially squatted over me and supporting her weight with her hands on her knees.

Then she touched my asshole and I moaned out, "Oh, Fuck! Yes!" My body tried to buck up into her, but I had almost no leverage and barely moved.

"So, will you let me play with you? Will you let me do your ass?"

She kept tapping and massaging my anus until I responded, "Yes. Yes. Yes."

"Mmm, that is good to hear." I felt her hand move from my anus to her vagina. Margot was still twerking her ass on me, but I also felt her start working her clit. At least I assume that is what she was doing.

The vibration from her clit twiddling was transferring into her vagina as she stroked up and down. "Randall! Get ready! I'm about to come!"

There wasn't anything I could do about it either way. Margot was using me for her own pleasure. Not that I minded since her pleasure was getting me off, too.

Jamming herself down onto me Margot started shaking through her orgasm and that caused me to shoot up into her. It was a surreal experience since I had done little of the work but had gotten all the tight stroking necessary for me to come. Amazon position was weird, but it worked for me. And Margot.

Once Margot got off me I sat up and realized that I had been using my upper abdominals more than I thought, they were a little sore. We lay back on the bed and Margot asked, "Was that ok?"

I grinned and kissed her, "Yes, but weird. I couldn't help at all with my legs up like that. I'm flexible enough to do it, though."

"And the other?" Margot asked. "Can I go all the way and fuck your ass?"

It was not something I had ever thought about before, but the brief contact was very erotic. And gay guys liked it, so I guess it must feel good to get fucked in the ass. Right? Even with a fake penis.

"You said I could do the same to you afterward?" Fucking Margot in the ass was something I had thought about.

Margot looked excited, "I never let my ex do it, but yes. If you let me fuck you in the ass, I'll let you do me the same way. Except I'll want you to come inside me."

I felt my desire build, but at the time my dick was done, "That seems like a great plan." We made out for a while longer before getting up to shower together. Her walk in shower made that very nice, too.

We made plans for the following Saturday evening.

I was nervous, of course.

Margot met me at her door wearing one of her sexy silk robes, the one with the big orchid across the front. She had the biggest smile on her face and drew me in for a kiss as the door swung closed behind me.

"Are you ready for this?" She asked as she took my hand and started walking toward her bedroom.

"Yeah." As she pulled me along by my hand I laughed, "Not as ready as you are, obviously."

"You will love it, I promise!" Margot was very ready; she had moved the hope chest further away from the bed so that we could access it from all sides. There were also a lot of straps and Velcro fasteners wrapped around it.

I stopped moving when I saw all of it, "Uhh."

Margot smiled and said, "I know it looks like a lot, but I saw that ropes could cause chaffing and since I don't actually know what I'm doing I thought these straps would be better. Wider." She kissed me as she started undoing my pants.

Margot had given herself to me many times, and she promised to let me take her ass later so I gave in and started undressing. I was excited by the idea of being unable to resist her. Not that I had any reason to resist her, I wanted to fuck her and to be fucked by her. "Ok."

The straps were complicated, but Margot had it planned out. The first strap wrapped around both my torso and the padded chest I lay on. The second wrapped around my stomach and the chest. Both of those also trapped my arms to my sides; there were Velcro wrist bands that connected to those straps. I could move my hands and wrists a little, but my arms were immobilized.

The last straps wrapped around my thighs just above my knees; when they were connected to yet another strap beneath the chest my legs were pulled apart and up to my chest. With the pressure and restraint of the straps I was able to move my hips more than the first time, although barely. Other than very minor movements I was fully restrained.

Margot kneeled next to me and kissed me. "What is your safeword, darling?"

"Applesauce."

"Perfect. If you say "applesauce" I will stop and release you right away." She kissed me again, and the feel of her tongue against my lips made me shiver. "But if you say anything else you will be punished!"

She slapped my ass and it was loud, but didn't really hurt.

"Ok." I said with a grin. We had agreed to the punishment clause and I wanted to test her.

Margot raised her eyebrows and then spanked my ass for real, and this time it did hurt. "Ohh!" escaped without my meaning it.

The strike also hurt Margot because I saw her shaking her hand as she said, "That is ok, and moaning is fine, just don't say anything. Ok sweetie?"

I started to open my mouth and saw Margot raise her hand again. I grinned as I nodded instead. Margot chuckled at my pushing the limits.

Margot stood up and moved to stand over my penis. Given that I was naked and expecting sex I was a little surprised that I was only partially hard. Margot traced her fingers from my knee to my groin and then carefully up and down my hardening shaft. I watched her movements and saw that Margot was watching me.

"Hmm, this won't work. You will know what I'm doing. Let's amp this up." Margot turned to her bed and pulled a couple of things out of a duffle bag.

The first were small cone shaped pieces of bright orange foam. She held one up in front of me and squeezed and twisted it. Stuffing it into my ear I realized they were disposable earplugs. As she squeezed the second one Margot asked, "Is this ok?"

We hadn't talked about this, but I nodded as she stuffed the second one into my other ear. The sensation was weird. I could still hear, but everything sounded very far away. There also seemed to be a humming noise, but I think that was my imagination.

The second item was expected, it was a sleep mask which she pulled over my head before leaning in and kissing me. I was plunged into darkness as she seated it over my eyes.

"Now we're going to do what I want to do. But don't worry; I'm sure you'll like it." Margot said. Even though she was right next to my ear she sounded so far away. Maybe she had moved away since I couldn't see or hear where she was in the room.

Something barely touched my thigh. I wasn't sure I felt it at first, but there it was again on my other leg. I couldn't tell what was touching me, but it didn't feel like a finger. Whatever the gentle touch was moved to my penis and slid up and down both sides. I started to get hard again but then the sensation stopped.

There was no contact for a while and then something warm and wet touched my lips. It was Margot's tongue and she swiped it across my lips several times before kissing me deeply. She moved away and I felt something else tentatively touch my lips. It too, was warm, but it was hard and dry. The scent was her familiar vanilla but included a very slight sexy sweaty smell that I recognized right away.

Slipping my tongue out to probe I immediately found Margot's hard nipple and flicked it quickly back and forth several times. I was rewarded by having her nipple brought to my lips so that I could suckle it. What ever the gentle touch on my dick was, it returned as I was distracted.

Margot moved away again and this time she moved between my legs and started licking me while running her hands around my body, including brushing over my anus. I was a little surprised that she moved to my ass that quickly, and I was even more surprised when I felt her start to probe me. Her finger tip was wet and slippery as she started to penetrate me.

"Mmm!" I didn't want to say anything else as she started to probe into me. I really didn't want her to use her fingers on me since she has fairly long nails and I didn't know how she could do it. The only penetration, at first, was the pad of a fingertip and it felt like she was lubing me up a lot. That was a relief.

She moved away again before bringing her face next to my head. "Lick this. You are going to want it as wet as you can make it." Her voice sounded so far away.

Margot pressed something hard against my lips and I reached out to lick it. It was obviously a dildo or vibrator of some sort. It didn't seem very big, maybe as big as a cigar? I knew where it was going, though, and did my best to get it as wet as possible as she started to fuck my mouth. I pursed my lips around the toy while swirling my tongue around it. In case you are wondering there was no scent, so either it was new or Margot had washed it well since the last time she used it.

As she withdrew the fake dick she kissed me on the forehead.

The toy felt much bigger as she probed it against my anal opening and gently slid it inside. "Uhn!" I almost said my safeword, but I didn't want to be a bitch and chicken out that quickly. Relaxing as much as I could she was able to stroke in and out several times, eventually getting almost the whole thing inside. It couldn't have been very long, probably no more than four inches. That felt plenty big enough, though.

Leaving the toy inserted into my ass Margot started jerking me off, and then started licking the head of my dick. I was approaching my peak when Margot stopped touching me and moved away. I realized that I was breathing heavily, and that my dick was twitching a little. I was so close.

But she left me alone. For a long time. I don't have any idea how long, though. Maybe it was only a couple of minutes, maybe it was ten. It was long enough for me to get used to the toy in my ass, and for the urgency of my orgasm to fade.

I only knew she was back when she sucked the head of my dick into her mouth and I felt her fumbling around with the toy. She wasn't really fucking it in and out of me, although it did slip a little further inside. What she was doing was turning it on.

I had never felt a vibrator before, and certainly had never had one in my ass. The buzzing inside was so intense that I felt my legs start to quiver. "Oh, Fuck!"

I knew I messed up as soon as I said it, and I hoped that she hadn't heard me.

She had, though, and she shut of the vibration. I knew that couldn't be all of the punishment, but it took a moment before I found out what the actual punishment would be. My dick was hard, obviously, and I was so turned on that my nipples were also hard. I've just got little vestigial nipples like all guys, but they were hard little pebbles. Until my left nipple exploded in pain. "Ohh!" A moment later the same thing happened to my right. "Oww!" I screamed.

The first punishment was to have my nipples flicked. I don't think Margot realized how much it would hurt. The pain was so intense that I couldn't even remember my safeword. If I had been able to remember it at that moment I think I would have said it.

Muffled, I heard, "Remember, no speaking!"

I think Margot felt bad, though, because she placed her cool palms on my nipples and that helped ease the pain. Returning to my still hard dick she held it straight up and I felt her straddle me and lower herself down. It felt good, but she only took a few strokes before sliding off and turning around to twerk on me.

It took a couple of changes to realize that she was taking ten strokes in each position before switching to the other. Sometimes she went fast and sometimes she dragged it out. Once she even slowly withdrew on the 9th before slamming down for the 10th.

The constant tempo and position changes kept me close and I wanted to come so bad. I even started fucking up into her as much as the odd position and restraints would allow. Which wasn't very much.

After at least ten or fifteen minutes of the most erotic torture I have ever experienced Margot sat herself on me and started twiddling her clit like the first time she Amazon fucked me. I could feel the vibrations of her masturbation and to be honest I had almost forgotten about the vibrator. I could barely feel it.

Until she got close to her own orgasm and switched the thing on again.

It was even stronger than the first time, I guess there are settings and she switched it on high. I think I could feel the vibrations in my bones, and it caused me to orgasm like crazy, shooting blast after blast of cum into my lover. My legs quivered and my hips rolled and I lost track of the world.

I assume Margot came as well, but I never thought to ask. By the time I had come back to my senses and was able to stop my hips from moving she had already pulled off. My legs were still quivering because of the vibrator, though.

I felt her turn the vibrator off before she started using her mouth to clean me off. I thought that was pretty daring since she didn't like oral without cleaning up first. She started playing with the vibrator again and started fucking it in and out of me. The cold drips of extra lube told me that she was trying to open me up. Inserting it all the way inside she turned it on to the lowest setting.

It was very stimulating, but having come moments before I was still soft. She left me alone for a couple more minutes before stepping next to me and placing a hard plastic dick in my hand. The strap on she had chosen was a surprise to me, she hadn't let me see it to me beforehand. It felt a little thicker than my dick, but not by much. It was definitely a couple of inches longer.

From far away I heard Margot say, "Turn your head to the side so you can get my dick wet. You are going to want that, I think."

I've always thought of myself as an experimental kind of guy, but I will admit to being concerned about taking a hard plastic dick into my mouth. Especially while restrained. Margot couldn't feel the dick, and if she accidentally hurt me how would she know? But I trusted her, so I opened up and hoped she wouldn't go too deep.

First she stroked the plastic dick across my lips and I wet it as much as I could with my tongue. Holding my face she put the tip into my mouth and started fucking it in and out. I was right to be concerned because after only five or six strokes she hit the back of my throat and I gagged noisily.

To her credit she pulled out and kissed my lips gently in apology before moving down to my ass. She stroked the small vibrator in and out a couple of times before removing it and placing it on my stomach. Resting the tip of the much bigger strap on just at my opening I felt more cold lube drip over my groin again before she slowly started fucking the dildo in and out of my ass.