**PART 1: Prologue**
**PART 2: The Experience**
In my early 20’s I was VERY adventurous with my sexuality. I had a nearly year long fling with a man 10+ years older than me, but it ended when he moved away. Somehow this left a void inside me. An itch that did not need to be scratched, but *wanted* to be scratched **badly**. This is how I stepped into the world of BDSM, met some amazing people, had many experiences I remember fondly even now.
**PART 1: Prologue**
A little under a year after my fling I was still unsure if I was Bi or just Bi-curious. Having been going to a BDSM munch for a few months and this was where I met my future keyholder. This was a surprise to me as I did not have a thought in my mind I would be the bottom/submissive. Yet somehow, we will call her Heather, had won me over.
Heather was a powerhouse of a person. 37, 5’3″, curvy MILF with kids in college, Divorced, and was often assumed to still be in her 20s. Her personality was witty, intelligent, and funny. She had a way of putting you at ease while she got what she want, and you somehow got what you needed. This was how I found myself locked in chastity by her.
When we went out with her friends, and they were all much like her in both appearance and personalities. They weren’t always dominants, some were subs, but most were switches. Her friends always would ask who was her new ‘chaste boy’ when they noticed her wearing a key around her neck, but she’d never say it was me. Unless I gave approval. I gave approval for her friend Meghan during a stint in chastity. Meghan was 32, 5’6″, curvy and fit, golden blonde hair, and still crossing things off her bucket list before deciding if she wanted a career and/or a partner.
Yet the way Heather put me in chastity was *so fucking hot*. It would always start with having me go over to her house. But this happened often so I could never predict to expect it. Heather was in control from the moment I stepped foot into her house. She didn’t approach it directly. See Heather had a thing for tease and denial. It was not uncommon for her to invite me over during our FWB BDSM relationship, have me strip naked, tie me down to her bed, and tease my cock, balls, and asshole (most of the time with toys) until I was *BEGGING* to cum. Heather would either be in a lacy bra or topless and wearing boyshorts. Always they were black.
Most of the time she would allow me to cum. Other times she wanted something in return. Most of the time what she wanted in return was eating her out for an hour or more. Other times for her to ride me until she was satisfied. This time she wanted my cock to be drained and locked up. If I did not want to Heather would let me cum, but only by my own hand. If I did agree she’d get me off with her hands or mouth. But immediately after I’d be locked up.
This time I agreed as I knew I could trust her, and trusted she had a goal for this other than to just control my cock with a chastity cage. The smile she got was beaming! It literally lit up the room. But before I could cum she needed to ‘clean me up’. This meant getting my cock and balls nice and smooth. She went into her bathroom and returned with a bowl or hot water, an electric razor, a razor, and some sugar scrub.
By this point she had been edging me for a little over 3 hours. I could not get soft without cumming. I’m not sure if you’ve ever had your cock and balls smooth as the day you were born, but it makes everything *so much more* sensitive. Then Heather left, took her tools with her, and returned the cage and an ice pack.
Before Heather locked me up she told me why. This time she wanted lock me up for a couple of weeks and try to push a limit I had discussed with her earlier that month at a munch. The limit was sharing me with a friend and to include pegging. Her friend had expressed she was delving into her Dominant side, and she wanted a young man she could peg to see if she liked doing it with women or men better. Heather mentioned she might be able to help her, but needed to ask me. Heather asked me if I’d be open, and I agreed. I was *desperate to cum* and Heather did not disappoint. She got a wicked smile, took my cock in her mouth, and slowly sucked me. I made a lot more noise than anticipated, but when I came she needed to swallow a few times to get it down. Once I was soft Heather was quick to put the cage on me. The lock clicked closed right as I was about to get hard again. She put the key around her neck, smiled at me, and jiggled my junk in the cage. “I own your cock, and you are my bitch, for the next two weeks. So long as you behave!”
On another bout of being locked in chastity by Heather she asked if she could share me with one of her friends. This wasn’t uncommon as it was one of the things I wanted to experience, but only with people I approved of and with her nearby to step in if needed. She’d shared me before with two friends. One a woman we both knew who wanted to experience if I was as good at eating pussy as Heather claimed. Another was a man, *much* older than me who wanted a blowjob from me, with Heather watching, while I was caged. Both times were **MUCH** more enjoyable than originally thought, and I’m glad I did them with someone I trusted.
Heather then untied me, teased me a bit for going back in the cage, touched her key to focus my attention on her chest and face, and told me to get dressed and she’d check in with me later that night. Morning and Evening check ins were expected. As were end of the week meet ups to let my cock breathe a bit, for her to tease me, be denied, and then put back in the cage.
**PART 2: The Experience**
On second, and last weekend of my stint in chastity, Heather asked if I was ready to be shared and pegged. I told her I was. She was very excited to watching me experience this. As normal I was naked, wearing just the cage, and told to get on the bed on all fours. This was new, but I agreed. My wrists were tied with rope to my legs just below the knee. I was over a towel, legs spread, ass up and face down. Then Heather surprised me a bit. “I have a requests from my friend.” I looked to my right to see Heather holding a blindfold. “They will be here in about an hour and requested you wear this. They only want you to know who pegged you after.” Realizing this wasn’t so much a request as a command I agreed. Besides I could still talk and stop this if I wanted.
With a giggle Heather put the blindfold on. The last thing I saw was the key to my cage dangling above her cleavage, her hair draping over it a bit, and the bottom of her smile. A moment later I felt hands around my cage and it coming undone. “Oh and my request is you cum from the pegging. If you don’t I’ll put you back in it.” She stroked me a little when she said ‘cum from the pegging’. Always a tease, in the best way, Heather is.
Then I felt her get off the bed, kiss the side of my head, and whispered, “I’ll be back with my friend. Just enjoy yourself.” I heard small footsteps leave her bedroom and then silence. I lost track of time and my mind wondered on who it could have been who wanted to peg me. If it even was a woman. About to get lost down the rabbit hole completely I heard small footsteps come back into the room. Whoever it was didn’t make much noise, they didn’t even talk. The first time I felt them was when they put a bottle of lube on the towel between my legs. Next some gloves. Then their ‘strap’. I had seconds to realize it was big, thick, and *heavy* before I felt them get on the bed behind me.
Now I felt vulnerable feeling them size themselves up to fuck me. I heard the gloves go on, the strap get put in the harness, and the lube bottle open. The lubed finger surprised me as it circled my asshole. Soon a slender finger pushed itself inside me. It twisted a bit, filled me with a bit more lube, and then another joined it. Then another. Soon I was getting finger fucked by three fingers, hard, and unable to stop from making noise. Then the fingers left my asshole. I heard something odd only to have the tip of a pointy toy fill me a couple of inches. I’m a bit embarrassed to say I cried out as the cold lube was pushed into me by what I could only assume was a turkey baster. I could feel their smile as they patted my ass. Needing this much lube got me a little concerned, and I heard a noise that filled me with dreadful excitement. They began to lube up their strap.
When the noise stopped I felt them shift behind me, grab my hip, and put the tip of their strap against my hole. It was **BIG**. Easily eclipsed my asshole, and felt almost 2 inches in diameter. I got nervous and tried to control my breathing as they pushed and stretched me out slowly. The strap getting further and further into me as they pushed. Then as I let out a gasp of pleasurable discomfort and surprise I felt it ‘pop’ into my ass. Well it was just the tip.
I was given a moment as they adjusted behind me, grabbed my hips, and then began to press their strap into me. My asshole was stretched more than I’d experienced before and was on fire. My hole was about to get wrecked, and I was about to get used like a fleshlight and I knew it. Soon I was being pulled back upon the strap’s shaft and filed up. It took minutes, I don’t know how may but easily 5, to fill me up completely. I’d never been so full! Whoever was pegging me was kind and gave me a moment to adjust to this new ‘intruder’.
After I had relaxed enough for them they pulled everything but the tip out. I’d never been filled so much the void it left was… a new experience. There was a pause of a few seconds before it filled me again. I made noises up to this point which were reasonable for a young man experiencing this. Yet as they built up a rhythm that… stopped.
Soon I was moaning, crying, and screaming into the pillows and mattress. Fully lost in subspace I became just like the girls in porn getting railed like I was. I was embarrassed, but also having so many prostate orgasms I didn’t care in the moment. After a surprising moment of clarity I remembered the only way I was going to cum was from getting fucked. For this to happen I had to give in completely. Mentally this was a bit challenging, but with such a large strap it happened before I realized it.
A moment later I was *begging* for them to fuck me. Use me like their whore, like a free use slut, all inhibitions lost. Only the desire to cum was all that was left. Like being lost in hyperfocus completely. Whoever was fucking me loved it and fucked me harder. They even thrusted in so the strap hit my prostate more.
Soon I was near shouting for them to fuck me. That I was close to cumming. To make me cum. A minute or two more I felt something build in me. My sentences became broken, then soon words were difficult to form, and then I felt it. My cock throbbed and soon I was cumming harder than ever before. My asshole clenching the strap as cum pumped out of me.
They didn’t stop fucking me when I finished cumming. I heard a vibe going as they quietly pleased themselves. They kept fucking me a few minutes until they came themselves. Soon the fucking slowed. Then stopped. After a moment I felt the strap pull itself out of me. I knew I’d gape. I didn’t know my hole could get so loose.
I laid there tied up, blindfolded, drained, gaping, and exhausted. Processing what just happened. I heard the harness being taken off and put between my legs. Next the gloves came off, they got off the bed, and untied my hands.
I laid there as I heard them leave the room. It took a few moments for me to get the ropes off my wrists and legs, move and reposition myself. I flipped myself over on the bed, only realizing then how sore my asshole was, and took off the blind fold. It was then I saw it.
The strap was *massive*. And I’d taken it all. Easily 12 inches, as thick as I thought, and frim. I could see on it where the lube built up fucking me. I’d taken all of it. I’m certain I turned red blushing from realizing this. Then I heard Heather from the living room, “Come out here, as you are, when you’re able to.”
On shaky legs I made myself stand up and made my way to her living room. There I saw Heather, her friend Meghan, sitting and giggling on the couch. Both were clothed, but made sure they showed off their bodies. Meghan got up, walked over, stood in front of me looking up into my eyes, and put her hand on the side of my face lovingly. “Thank you for this.” She smiled an erotically charged smile. “You make lovely noises. I’ll remember this for awhile to come!”. Then she grabbed her purse, and made for the door. “Thanks for having me Heather. We need to do something like this again sometime soon!”.
After she left Heather gave me some aftercare. But first she had me kneel, legs open, in front of her. She smiled down at me, “You looked like such a hot slut taking something that big like a seasoned whore!” I turned beet red from embarrassment. “Now, lets go take a shower.”
Source: reddit.com/r/gonewildstories/comments/skthd3/mf_the_time_my_keyholder_pushed_my_limits_femdom
What a sexy story! Thanks for sharing!