A Mostly Unpleasant Surprise Part 4
- 3 years ago
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A Very Unpleasant Evening free porn video
There was one very bad incident where I was blind-sided by an older guy I’d met at one of my favorite bookstores. He led me into it slowly, over a period of months while, all of the time, being very loving and kind.
I’ve been ****d five times. None of them were pleasant and two of them were with multiple assailants; a few to hold me down while they all took turns. Normally I was/am very careful – letting my guard down got me in a position for this to happen. Sometimes, being a slut – like being a hooker – can be dangerous. This was one of the times.
Also, those who have read some of the stories about my growing up, know that my father was very strict, very straight and, didn’t have a problem taking his little boy-slut to the ‘woodshed’ to try and whip my little ass straight.
There was some arousal in that for him; many times he’d have a raging hard-on while he was punishing me. Did he really want to finish the job and give me a good hard fucking after he punished me? His hard cock was saying that he did. I would have gladly bent over (or stayed bent over) to trade half of a whipping or paddling for a quick fucking or, just got on my knees and given him a good sloppy blow job – anything to get out of it! My uncle knew how to get that done…warm my little ass up, get me just into tears and very willing then, give my young little boy cunt a good hard fucking! He was good at it.
I was used to being punished, seemed to attract more dom partners and, suffered through some BDSM films and videos just for the money. I also had two bosses that punished me because they could. I can be a brat at times and realize that I need my backside warmed on occasion – just like any other brat or bitch. Jack knew that and, knew how to handle me with love and loving discipline. Roger was the same way, the only big difference was that it aroused him to bare my backside and turn it red while I raised hell over his lap.
This guy was just beating me to beat me. He truly enjoyed all of it. He layered hours of pain over a big area of my backside and thighs – knowing just how to do it so that nothing was ever ‘numb’ but always burning and throbbing at the peak of roaring pain. That makes it brutal. Just pain for the sake of pain.
I suppose that there were some signs about him but I missed all of them, it was a learning experience and I still have a few marks from it. We met in the bookstore, after I blew him through a glory hole he’d whispered that we should meet outside and go somewhere for a while. We talked for a little while, he suggested a motel room and we had a very nice few hours that night. During sex I had my hair pulled and, had my backside slapped pretty hard numerous times. It still tingled on the way home – I just put it down to a guy that got a little rough once in a while. Over a period of maybe 2 months I was introduced to normal spanking, face slapping and, some mild bondage. Eventually the restraints became more common as did the spanking, a razor strop and a paddle. I was going back for that nice thick eight inch cock of his.
I was always dressed for our meetings and, he even bought me some nice things he wanted to see me in. He introduced some toys to our play, which became bigger as time went on. When we went out, I was normally made to wear a larger butt plug or dildo – these times I would wear a panty girdle to keep the toy in. Then, he found a butt plug that gave new meaning to ‘uncomfortable’. It was eight inches long, two and a half inches across at the widest part and, had a rough ‘non-slip’ finish. Getting it inserted wasn’t the most pleasant thing in the world – getting it out was worse. Once in, it did stay in place, damn, did it stay in place. I could wear panties when it was in (with no fear of having it slip out) or, in shorts or slacks, nothing but a gaff.
I was paddled a few times, while wearing a girdle. He was the second guy to do that; the girdle makes the paddle sting more and, it is much longer lasting. The tight latex held the heat in to really roast my backside. And, like tight shorts or jeans, your cheeks can’t bounce and flex; that really increases the damage and level of pain – especially with a paddle!
The pain level went up over time until I was reduced to tears on a few occasions.
Then one night, I was given a paddling, in a long-leg panty girdle, that had a lasting effect. Not only did I bawl my ass off but, couldn’t sit at all when it was over – although he made me sit down for a while – I called off work because the bruises were so bad I had trouble walking. Sitting for hours at a time was out of the question for a few days. I spent a lot of time in a cool tub or, with an ice cold towel on my backside while lying in bed. It was a pretty bad one.
After that, things calmed down for a while. I carried the marks from that paddling for weeks; the marks from the large holes in the paddle. He knew exactly what he was doing with that paddle too. Each mark was a circle with a raised bruise in the center, outlined by an ashen white circle. The worst ones were all over my ‘sit-down’ area, they covered it. Material of panties or slacks were an irritation when I walked (and it was uncomfortable to walk for a few days), sitting was uncomfortable. I could clearly ‘feel’ the marks, every one of them. I could feel them blossoming as the paddling was given then, later, feel each one as the pain around them went away – the pain from them didn’t go away as fast.
His favorite form of play was ‘spanking the naughty wife’. Most of the time it was just spanking; pealing down my clothes until my bare backside was getting a very good blistering. I found out that, the more demure and submissive I was, the more I struggled and begged him not to spank me and, the more I kicked, wiggled and cried – during the spanking – the more he liked it and, it turned him on more than any ‘pill’ could. There was also some public embarrassment. His favorite was to tell me, loud enough for a waiter, a bartender or some patrons, “Wait until I get you home…that backside of yours is going to get a spanking/paddling/whipping that you won’t forget for a while.” Then, take me by the arm and march me out of the place like a naughty wife/girlfriend.
I didn’t think any of this was too bad. My father had tried to beat me straight while I was growing up, I’d dated and lived with a few dom guys; I had also been in some porn movies. Some had gone into the world of BDSM so I’d taken some spankings and paddlings on film. Most of the time it was easy for me to take the pain, relax completely and, begin to cry like a little bitch. This is what most guys wanted (along with wiggling around and kicking) so, once spanked to that point, they would stop.
He wasn’t one for stopping. I may get a little break to calm down and relax a little, take time to blow him but, the punishment would continue until he was satisfied.
I had no idea what I was being led into. Sex with him was pretty good…I always (stupidly) went back for more.
He called me one night and gave me explicit and exact instructions as to where to go and what to do. It was at a hotel we’d used before and, I was to go there early and be ready at a specified time. When he arrived I was to be standing in a corner and not look around when he entered the room. I went there and got ready then, got dressed and waited. An hour later I’d been slapped pretty good a few times, that put me in tears, I’d been face-fucked while kneeling in front of him then dumped in bed and fucked very hard.
Following that I was given a pretty hard spanking then stood in a corner, holding my tight skirt up with the garter belt and stockings framing my very sore red ass. I was standing there when the pizza he’d ordered arrived and, still shaking all over and, crying a little. My ass felt like I’d sat on a hot griddle and this was just the beginning of it.
I was allowed to eat one slice of pizza (the delivery guy had seen me in the corner with my red ass on display) then, I was put in bed with a leg-spreader bar attached to my ankles, my wrists were tied to the corners of the bed, I was on my tummy, the skirt was up around my waist and he’d inserted a butt plug. That’s when he opened the bag he’d brought and went to work on my backside and thighs with a leather strap. For the next few hours I was spanked, whipped and paddled; when he got an erection he fucked me hard. His favorite paddle was one with three rows of larger holes in it; that thing stung like fire! When he wasn’t fucking me I either had a butt-plug inserted or he fucked me with a dildo. The size of these became larger and larger as it went on. I buried my face in the sheet and bawled my eyes out, my face in a puddle of tears, snot and drool. The pain of the punishment overwhelmed me to the point that I was sobbing out of control…trembling from head to toe.
The most severe trembling was happening in my backside and thighs. They just quaked and I couldn’t stop it, couldn’t control it. I was released once to use the toilet, he escorted me there – I stumbled along with the leg-spreader still in place – he watched me sit slowly and carefully then, walked me back to bed. My poor backside and thighs were just throbbing like hell.
The pain became brutal after a short time, everything from my waist to my knees was a burning stinging mass of spreading pain. There were some moments of what seemed like caring and tenderness from him – followed quickly by another brutal attack on my tortured backside or cunt.
When he tired of playing with me I was gagged, my restraints tightened then, he brought an old glass Coke bottle out of the bag and showed it to me. I didn’t know it but this would be the final butt plug.
Using the top of the bottle, he eased it in deeper and deeper until I started to wiggle around and scream into the gag. He’d stop then and allow it to slip out slowly. He repeated this over and over, stretching me more every time until, the last time, he kept pushing…until my cunt closed around the ‘pinched’ part of the bottle. The pain was horrible, it was a lot more intense than what I felt from my tortured backside and thighs until; he started whipping me with the strap again. Slowly and, very hard, he finished the whipping; from just above my knees to the top of my cheeks.
By the time he stopped, that entire area was just throbbing with pain. I could feel almost every one of the stripes he’d caused with the strap and, the hard welts from all of the previous punishment. My bladder had been pretty full; I emptied a little more of it during the whipping. It was impossible to hold it. He played a little more, with the Coke bottle then kissed me a few times and left…after taking a few pictures. For a while, I thought he was coming back to untie me, as the hours slipped by I realized that he wasn’t. I slept fitfully, when I tried to move the pain woke me up, my bladder became painfully full and, after waiting for quite a while, I just soaked the mattress with pee. It was impossible to hold it. I did work at getting the gag out of my mouth, finally succeeding.
I was left for the indignation of being found by the maid. That couldn’t have been more embarrassing! Bound and, with my backside and thighs looking like raw meat, partly dressed and laying in a bed soaked with pee, spotted with lube and cum…and, with a Coke bottle shoved halfway into my cunt.
When she (the maid) entered the room I begged, I pleaded with her, to at least untie my hands. I could do the rest. She did it then left in a panic.
The most difficult (and painful) thing was getting the Coke bottle out. That was at least half an hour of pulling, straining, flexing my sore little ring of muscle and tears. My sphincter had closed around the narrower part, I had to stretch everything all over again to remove the bottle. This, while every move I made , brought new flashes of pain to my backside and thighs, I was a mess.
By the time I’d cleaned myself up, my gaping cunt had closed a little. I didn’t do much to myself, just enough to make it to my car. It hurt to walk, it hurt to bend hell, it hurt to move! There were two rows of welts, just inside of my cheeks, that rubbed together when I walked. They were from the paddling and, made walking painful as my cheeks rubbed together. My entire backside, top to bottom, as well as most of my thighs, was one big striped bruise. When I moved it felt like my skin would crack open.
I repaired what I could, slipped into my panties and hobbled to the car. It was painful as hell to walk and even more painful to sit down. All I wanted was to get home, get some cold towels on the most painful areas and relax for the rest of the day. It was Sunday morning; I’d make the decision, to go to work or not, later. As a PA/sexretary, I spent most days sitting. That was pretty much out of the question for now.
This was one of the jobs where the boss was fucking and disciplining me. His fun would be put on hold for a while. As it was, it would be a full week until he bent me over his desk, warmed my bare bottom up a little then fucked me; I still had some marks that hadn’t gone away then. There were a few phone calls (from my boss) while I was off. He wasn’t happy about my absence at all and, I knew that I was facing some discipline when I returned to work. His promised spanking would be nothing compared to what I’d taken and, it got me his nice big black cock when it was over, slow and deep.
The promise of that was something I was always up for.
Vera
- 15.11.2022
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