Hi, I’m back! In the last story I shared, I started my 2-year long enslavement by my master, Mike, my high school bully. Now, I want to give a fair warning this time. My sex life with my bully was a BDSM dom/sub relationship. I never did anything against my will and did say no to him from time to time, but frankly, I had way more fun when I said yes. I did most of what Mike wanted and I loved it, when I’m degraded, insulted, and ordered around I feel like I’m at my most calm. I know that may sound weird to some, but I spend a lot of time overthinking things and questioning myself, so it’s such a wonderful break to be controlled, I can just turn my mind off and feel great and please others.
***Fair warning, the following story contains these kinks: Cheating, submission, rimming, degradation, insults, prostitution (?), age gap, unattractive male partner.*
*TLDR:* I fuck an old unattractive stranger for an unknown exchange of goods or services. (I was going to make this a shorter story, I don’t know why it got so long. So many memories came flooding back to me)**
At this point, I had been serving my bully for over a year. I’ll admit that I stupidly went through phases of being in love with him but I realize now I just loved his cock and the way he fucked me. He was an absolute garbage person and I’m sure he still is to this day. During the school year, he would often meet me in the disabilities club room where he first fucked me. Usually, he would only fuck me outside of school, but I would serve him in other ways. He’d text me, tell me when to meet him and where, and I would show up, get on my knees and rim him and/or suck him off, even after he worked out without showering.
He had been dating his bimbo girlfriend (also his bimbo future wife) for a few months at this point and the frequency of our meetings never faltered. I would even go on dates and have relationships with guys that knew nothing about this. He and I were never caught. The sneaking around just made it hotter to me (no regrets, judge me all you want). Going on a bad date and having them drop me off at ‘my place’ afterward, only to be riding his dick 5 minutes later, made the night so much better.
Mike called me over one Friday night (Bimbo’s girls’ night out) and he gave me a new task. I was to put on my slutty outfit I brought, go two floors down to Apartment 23E, and fuck the man inside, doing whatever he asks. This was a pretty shocking order, I had fucked one of his friends before (maybe two at this point, I can’t recall) but never a stranger. He gave me a look that said “So, are you gonna do it, or chicken out?” or maybe it said, “You’ll say yes, it’s just a matter of time, whore.” He knew I always wanted to fuck a complete stranger, one whose name I didn’t even know (Jacob was a relative stranger when I first met him), and since he kept pushing my boundaries making me do dirtier and dirtier things. I took it as a challenge and put on my outfit.
I’m 5’5, my hair is naturally brunette but I honestly can’t recall if it was dyed at this point (my hair is also super curly), my breasts aren’t the biggest but they’re perky and rounded so I like them and I probably weighed around 125lbs at the time. I put on a faux leather mini skirt that didn’t even try to cover my ass, fishnet stockings, black heels, and a cropped black denim jacket that showed off my midriff. I buttoned up the jacket with nothing underneath and after my inspection by Mike, he slapped my ass and sent me on my way. If you’re wondering why I didn’t show up wearing this to Mikes, you’ve never been a woman in a Canadian winter. Layers first, sexy later.
I asked a few questions before I left because my heart was in my throat, so freaking nervous. So I knew he was much older, probably 50, scrawny with a beer gut, and bald. He also needed to wear a condom. I didn’t want to know his name but I did find out that I was doing this to pay for something. I may have also done two shots while getting dressed to build up the nerve.
On my way down, I took the stairs to avoid running into anyone at the elevators (I really looked like a whore and it was quite embarrassing, but thrilling.) When I got to 23E, I knocked on the door, stepped back, and stood straight so he could see me through the peephole. When he opened the door, I thought that Mike’s description was pretty accurate, except he was closer to 55 and his horseshoe bald pattern was mostly grey with some patterns of a dull brown. He wasn’t wearing a shirt, just denim jeans and socks, holding a beer. He did have a pretty big gut but was rather skinny everywhere else. He also had a small chin which disappointed me. I like chins. His apartment reeked of cigarette smoke, even from the hallway.
“Get inside. Take your heels off.”
I guess he didn’t like that I was as tall as him with my heels on, so I took them off once I was inside. He locked the door behind me which made me pretty scared. And he wasted no time, groping me immediately like I was a prize show dog being inspected. Grabbing my ass, lifting up my skirt to look at my little pair of panties that barely covered anything, and spanking me towards the living room. He went through the kitchen, getting another beer and meeting me in the living room. His place was a bit of a sty. All of his furniture was old and poorly kept. He had several full ashtrays on various surfaces and his carpet was filthy. I was not looking forward to kneeling on it. Mike lived in a decent but old building, so it was surprising that someone could have the same apartment, but one is decorated by IKEA and the other is decorated by a dumpster. The television was one of those old giant CRTs, sitting on a couple of milk crates and plywood and a few stacks of porn DVDs and bargain bin movies laying around. Frankly, the adrenaline of doing something so taboo was the only thing keeping me going, this stranger wasn’t attractive to me, AT ALL. He sat down on his couch, which seemed to sink too much under his weight, and lit a cigarette. I was frozen in place standing next to the TV, probably shaking and looking around like a scared pup, but when he started undoing his belt and pants, my attention went back to him.
“Come over here and get on your knees. You’re suckin’ it first.”
I realized he had a bit of a rural accent to him, one of those Canadian backwoods accents that are kinda hard to nail down. My uncles and aunts have a very similar accent, and for the rest of my time there, it felt an uncle was giving me orders. I got on my knees in front of him and the carpet was worse than I thought, covered in crumbs, ash, and hair. When he got his pants off I could finally see his dick. Not bad, 6 inches, that had a very thick top half, and rather skinny bottom half. He was also uncut and there has always been something I loved about uncut dicks. There is more to play with and maybe being raised Jewish made me think uncut boys are taboo or something.
When I was this close, I realized he was freshly showered, you could smell dove soap on him. Not that it mattered when everything else around you smelled like ash but I went to work. I sucked his cock, jerking him off in long strokes so I could watch the skin of his cock come down and back up. I sucked and licked everything that was covered by the foreskin with glee and continued to play with his dick as he fiddled with the remote to his tv. I started to hear porn from behind me and I turned and saw he was watching some scene of a bolt-ons blonde bombshell getting railed by Manuel Ferrara, who is very sexy. This hurt me a little, I was probably the hottest girl he’s had in years, definitely the youngest and he was watching some MILF porn instead of me. I worked a little harder to see if I couldn’t get his attention. His gut did get in the way, but he kept pushing my head down to make me go further.
I followed a few orders, I took my tits out for him and even tried to give him a bit of a lap dance but the sunken couch made that really hard so it stopped almost right away. Eventually, he stood up and started to face fuck me, yanking my hair hard and shoving his dick as far as he could, his belly stopping me from taking it all the way effectively. At this point, I was very wet. I loved how degrading and insulting this whole thing was, and I just knew Mike was upstairs, ready for me to come back, freshly fucked. The stranger dragged me up to my feet by my hair and told me we were going to the bedroom. He smacked my ass, HARD, and followed close behind me.
I’m not gonna go into a long description of how awful the bedroom was, but let’s just say, if the living room was decorated by the dumpster, the leftovers were all over the bedroom. He pushed me onto the bed and grabbed a condom from his bedside table, slipping it on and climbing on top of me. I spread my legs apart and looked down to watch his cock slowly push into me, I love watching this part. I was probably breathing heavily and biting my lip, knowing me. Then he did something surprising, he kissed me, deeply, thrusting his cock in as far as it would go at the same time. I let out a little screech/moan and I think after a moment I started to kiss him back, even putting my hands on his cheeks to keep him close. He tasted as the place smelled but I just tongue wrestled his fat clumsy tongue in my mouth. This man was possibly older than my dad and I had my legs wrapped around him and was making out with him like we were teens.
He got off me for a second and grabbed a digital camera off his nightstand, a pretty clunky old one, and was about to snap a photo of me so I covered my face. But he barked an order, telling me to put my hands down and I did, but I did flip him off. So if you see a photo of a girl on a messy bed, topless, and flipping off the camera, I guess he put the photo online lol. And please tell me if you do, I’d love to have the photo myself.
I think a combination of his taste, the taboo of fucking a much older stranger, his top-heavy cock pounding into me, and him whispering to me, calling me his baby girl, which all led to me cumming. I’m quite the shaker when I cum so it wasn’t hard for him to notice, but unfortunately, he came quickly after. At the time I was relieved because part of me wanted it to end, but now I wish I had more memories with him from that night.
He told me to get dressed and put his jeans back on, went back to smoking and drinking on the couch. I dressed in front of him since most of my clothes were there, what little there was. Before I left, he simply told me, “Tell Mike he’s all paid up.” The whole thing was probably only 30 minutes. And that’s being generous.
And that was it, I went upstairs to Mike’s, I was spotted in his hallway looking like a tramp by his neighbour. Mike fucked me, but not until after I showered. God, I still remember some of the beautifully degrading things he said to me that made me cum so much that night. Calling me a prostitute, a whore, telling me how if I knew how cheaply I was just sold I would be disgusted. I miss that big dicked asshole sometimes.
I didn’t go home until about 2 a.m. but once I did, I had very little sleep. My boyfriend, Shawn, was picking me up at 7 am to go for a long hike outside of the city. He would have no idea what I spent the last 12 hours doing.
Thanks for staying this long! If you got hard at all reading this, I always appreciate a dick pic. xoxo til next time.
Source: reddit.com/r/gonewildstories/comments/ryf30q/ugly_duckling_f20_is_sold_by_her_bully_to_a_much
Hot:)
Did you give the stranger or Mike rimming that night?