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Kavindhu34 Kavindhu34 22-25 64 Answers Sep 16, 2010

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I was at an older guys house to watch ****. Looking back I guess it wasnt a good idea to wear those blue corduroy short shorts that I had hoplessly outgrown. But I did like the feel of the corduroy on my bare bottom. Soon we were both lying on a sofa, he in back of me watching the ****. He started to massage my bottom. His hands went into my pants massaginf my crack. I could guess what was going to happen next. Slowly he slid my short shorts down my legs and off. Now I could hear his pants being undone (zipper -button bein undone). He was whispering how much he wanted to **** me. I was shocked and scared - but was curious and horny. His soft hands massaged my cheeks like kneading bread. Soon he was rubbing my crack and then he put his finger (and fingers) into my anus. I was getting so excited - my curiousity got the best of me so I invited him in. From sliding his engorged **** up and down my crack, he told me to hold my cheeks and open up. I heard him open a condom wrapper and felt him fidgeting as he put on his "glove". As he continued to whisper how much he was going to **** my brains out, I felt it go in. The feeling was overpowering. It hurt a little at first (the first inch always does) but soon I felt pleasure as he went deeper inside me. He started moving in and out slowly and gently but was soon picking up his pace. I'm sure that anyone in the apartment building could have heard the loud slapping of thighs on bare *** cheeks. He let out a loud moan and then withdrew. He put my short shorts back up. At first I felt ashamed of my first time. But after about a week I wanted it again.

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My first anal was when I was 17 and was picked up hitching by a truck driver who was in his 40s - had a bit of a gut, beard and was quite hairy but not hirsute if you know what I mean. I had already sucked him in the cab of his truck and we got a motel for the night. He kissed me and ******** me. I had practically no body hair and long hair (in the 70s a lot of us did). His **** was huge - I guess about 8" and a lot thicker than my six inches were. He sat me on a couch and sucked me a bit and fingered my anus. He was quite gentle. He had some vaseline and lubed me up a bit and soon he entered me. It was incredibly painful and I remember begging him to stop, but he said it would pass, and it did. Once he was deep in me, he began to move - slowly at first and then he built up to a regular rhythm. I had my legs wrapped around him like a girl. He was kneeling on the floor and his belly was pressing on my ****. Eventually I came. He stopped kissing me and leaned back and ****** me until he came inside me. We did it again that night and the next morning at the motel. When he dropped me off I sat on his **** in the cab of the truck for one last ****. My bum was sore as but I was incredibly turned on the entire time. I never had anal again. I am now 50.

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i hope i get to do some thing like this some time

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That's a great story.

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wow, I am amazed you never repeated the experience.

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I would love my first time to be like that, great story

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My first time was many years ago as a teenager when I spent a month at a residential ballet school. I'd fallen for this boy a year earlier, but hadn't dared to approach him. Then been a year older and a year bolder I strutted my stuff in front of him after class one day. I'd tried to make it obvious all through the day's classes by chatting to him every chance I got and at the end of the day I was rewarded when he waited for me to gather my stuff together. We smiled at eachother, kissed and went to his room. I remember him gently pulling down my tights and taking my **** in his hands as he sank to his knees and then gently taking my **** in his mouth and giving me a most wonderful blow job. We kissed after I'd *** and I could still tatste the *** on his lips. He asked me to get on his bed on all fours and he gently inserted a lubed finger into my love channel, then another and finally a third before withdrawing them and shoving 9 inches of rock hard **** into me. I remember it hurt like hell, but as he started to **** me the pain went away to be replaced by intense pleasure. I'd never felt anything like it and when he shot his load the feeling was out of this world. He slowly withdrew his limp **** and I felt his hot ***** dstart to run out of my bumhole onto my leg. What beautiful memories!

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that's a lovely story I did a few summer intensive and met some lovely boys along teh way

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My first anal sex - as a bottom - was wonderful. My partner was hot and hung (9.5 inch black monster ****). We just met earlier that night and I told him I was an *** virgin and I wanted him to be the first man to ever **** me. That turned him on beyond belief - and turned me on even more!<br />
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He was the perfect big **** top for a first time bottom. He was slow and careful and he ****** me the way I told him to. Slow at first then faster and deeper as I got comfortable.<br />
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I came with his **** in my ***. He was ******* me from the side and we were making out passionately, and he jerked me off as he ****** me and as we french kissed until I shot my load.<br />
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Then he pulled his **** out of my *** and took off his condom so I could suck him off and make him *** too. Which he did soon after I put his big black **** in my mouth.<br />
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After we were done ******* we hung out for a while on my bed. I asked him to give e a grade for my first time *** ******* and he laughed and said I got an A-plus. Then he asked me what I thought about the experience and my answer was that I enjoyed it and that it was hot sex and I was glad I finally did it. And I'd probably want to do it again, but if I had to choose between ******* girls or getting ****** by guys - only one and never the other - I would choose ******* girls without a doubt.<br />
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His reply to me was that whenever a gay guy (like he is) has sex with another man, he always knows after only one **** if that man is gay or bi or straight. And he knows there is no doubt that I'm straight.<br />
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Which surprised me since I was a great first time bottom and I consider myself to be bisexual - around 90% straight and 10% gay but gay enough to enjoy being ****** by a big black ****.

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i feel the same about my sexuality but id never tell any one

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I feel the same also

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the first time i had anal sex it was fantastic i had always wanted to try it , the adrenalin that flowed through my body as his **** slid gently into my anal ***** with my knees up to my chest so he could talk dirty to me as he got faster and harder thrusting deeper into my gay **** as i wanked myself with him it was the most awesome sex i had ever experienced as he shot his gay babies into me and *** myself , o baby love ****.

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It feels awesome! Imagine an intruder pumping in and out, touching just the right spots! If you do it in missionary you can see the pleasure in his face! His **** will be pulsing and throbbing inside of you! After adjusting you will feel unimagineable, fufilling pleasure! You should be able to feel the head of his **** moving inside of you! If he last long enough, you will feel your body begin to quiver and then start to shake! Most awesome feeling ever! You should have extra bounce in your step for a week or two!

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no I didnt on my first time...I was with my first gay lover at the beach, and he knew a buudy who packed 8 inches and knew where he was staying..(hmmm guess maybe Mike had him earlier) we stopped by after a couple of beers at local club, and proceeded to light up and smoke a couple of joints, Mike said, to help me relax(right there I KNEW something was up). so here we are , with a attractive guy to make a great *********, so we jumped in each other, taking turns doing oral//getting...,,,this guy packed a NICE 8=9 incher whic was almost too big to service orally..att that time I I just knew Mike, and a couple other guys, who erer slightly above average like me, 61/2 inches...somehowm the tables got turned as I got rimmed for the first time that night, then felt a finger up my butt...at tfirst it made me 'freeze', but Mike told me to relax and pretend I was taking a sh..t...that thought seemed to work, then I got 2 fingers and then the real thing...at first, it hurt a bit, and then when he was in allthe way, My G spot was rubbed and felt like *******...he lasted QUITE a while, for I came before he idid, with a volley of spurts, more than I ever saw before from my loins--while Mike watched(he LOVED to watch guys get off) and jacked off...I was able to catch HIS load in the last couple spurts<br />
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gawd, I bled for a couple days but loved it....then when I had a date 6 months later, I topped my date one morning when we woke up together...That felt so good, when he came, his hole tightened on my ****, making me in volcanic spurts in his butt

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If you have a good, patient, caring top for your first time, it feels amazing - unbelievable! When the top is not patient, doesn't care about you and only cares about pumping himself off, well, it can certainly hurt to the point that you don't/can't enjoy it. <br />
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I was very fortunate that my first involved, serious, anal **** was with a top who not only was patient, but only had about a 5-6" ****, so it went very well for me. To the point that I couldn't wait to get nailed again! First, we had played together a few times before we decided to ****, so I was comfortable and trusting of him. Then, before he took me, he gave me a real nice *******, used a finger, then two, got me all relaxed, such that before too long, I was really ready for it.<br />
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When he entered me and I felt him slide all the way into me, it was perhaps the best feeling I've ever had with sex! It felt incredible, not only physically, but mentally as well. I was able to escape into a fantasy where I was a women getting it from a guy. So, emotionally it was as good as physically. As much as I enjoy getting taken, it never feels as good as the first time. Well, the first time I was taken when on poppers was also incredible. I was begging for it.

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My fist sexual anal was three years ago. He was three years older than me and bisexual all his life. He got me to a motel and once there, he took me from behind.<br />
But first he kissed me thoroughly along my body. He got to my **** and sucked it almost until I got crazy. After that, he took my ankles and turned me over a pillow with my *** rose to him. I was prepared to get ****** but instead he rimmed my *** in a way that made me twist. When he got my *** relaxed he put himself behind me and started to push his **** inside me slowly. The first two inches didn´t hurt but when he got all his way inside me, it hurt a bit but it was great. He drove me crazy.

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I've always loved being done missionary style. Besides what was mentioned earlier, I love to be able to wrap my legs around the guy who is giving me such pleasure. That way, when I want him to be more forceful and to go deeper, I can do it by pulling him towards me with my legs and he knows what I want wordlessly. My wife has always loved missionary style, both anal and vaginal, for exactly the same reason. It's a myth that being on your back is either submissive or passive. Sure, so people just lay there waiting to get it over with, or to feel dominated. But we like it for just the opposite reason.

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Was walking home from school and walked by a house with a dirty blonde guy standing in his attic style room. He was wearing a short robe and once we had eye contact he let it fall open to reveal his muscular chest and a gorgeous hair trail that led to his **** that was swinging back and forth into view. I had never experienced this kind of thrill before and could feel this guilty pleasure of excitement but was scared at the same time. Looking for anyone coming I just stood and kept looking up while hanging onto the bus stop. My heart skipped a beat when next he was at the side door of his house motioning to come over. He asked if I would like to come in for a bit and maybe see some more. Looking at his legs and strong forearms, I could see a nice carpet of dirty blonde hairs all over. We went to up to his room and he sat at his desk facing me with legs spread apart while I sat on the end his bed. He said his name was Steve and said he had seen me walk by before and smiled saying he finally got my eye. He had it again because his nut sac was rolling up and down and these two huge eggs were laying on his chair. I was practically stuttering when he asked if I like to see guys dicks and said he did. His robe was now fully open and this enormous **** was getting massaged right in front of me. He was uncut and I am not so watching that skin come up and envelope the head of his **** and then stretch back again was so awesome. He asked if he could see me without my shirt on and maybe more. I took off my shirt then decided to ditch my pants as well. He said he liked smooth guys like me the most. Then flat out asked if I would like to touch him. I moved forward without saying anything and had to get down in front of him to do so. Started touching his hairy thighs all the while watching that **** which was standing at attention. Moved up to his balls gently and upwards to his shaft and started moving that skin around the head like he was. Something about that even today, besides hair, that turns me on. He asked if he could touch me or check me out and I got up and laid back up on the bed. He asked if he could take off my shorts and slipped them down and off. He then got up on the bed and straddled me with his legs with his **** hanging right down and rubbing against my chest. I went back to stroking him and he was leaving little drops all over me. He then asked if I wanted to try putting my **** in his mouth? Sure enough he took me in his mouth and the swirling tongue and light sucking had me ready to *** but he stopped and asked if I could try it out on him. I tasted his saltiness on that huge **** and before long he was back on me. He lifted my legs and started licking my ***! Then he worked a finger into me which kinda hurt. It was another day and lots of finger and lube later that he mounted me. Once moving in and out I felt myself start to tighten around him. His fur on my back was the awesome. Shot so heavily it was amazing. Loved it ever since.

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My first anal experience was when I was in my third year of comprehensive school ( I was 13). I met this 18 year old on Facebook called Shaun I recognised him as he was in sixth form in my school. I started asking him if he was gay he said yeah am I? I said I'm bi-curious and I desperately want to try it. So we arranged to do it in the school gym at lunchtime the following day. So I met up with Shaun in the gym at lunch then we both ******** naked and started wanking each other off. Then we got into the 69 position until eventually he lubed my *** hole up and slowly inserted his 7" **** in my ***. I let out a huge groan that echoed in the gym, then he *** inside me. We got caught by a teacher they phoned our parents and sent us home. I have since be a homosexual this happened two tears ago I'm now 15 and Shaun is 20 I am living with Shaun and we continue to **** every night.

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I haven't had my first anal sex yet but i want to, im 14 and i want to have a huge **** just inside of me and then *** inside of me. <br />
Anyone out there wanna **** me hard and *** inside me and ill even give you a ******* you will never forgett and you can *** on my face and i will swallow ;)

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My first time was in my mid 20s just after I’d moved to a new town and new job. Shortly before moving I’d met a guy my age in a bar who also wanted a change of job and town and asked if he could move and share with me. I was reluctant as we had nothing in common, but couldnt think of an excuse that wouldn't offend him, so I agreed. Having little money all we could afford was just one large room, sharing a double bed; no big deal I tried to convince myself, I'm sure a lot of guys sharing have this arrangement. The first night, lying on my side with my back to him, trying to get to sleep, I felt a tug on my pyjama trousers and felt them being pulled down, then a greased finger probing into my bum-crack. I didn’t know what to do so just pretended to be asleep. I tensed as the finger went up my hole probing around in it then withdrawing, then a sudden sharp pain as the head of his penis suddenly entered my bum-hole. I tensed again and he quickly withdrew, then reinserted it, more gently this time. It was still painful but bearable though I found it impossible to relax to lessen the pain. He slowly thrust it in up to the hilt so I felt his pubic bush rubbing on my bum-crack, while he gripped my shoulders from behind for support. He thrust it slowly in and out for what seemed an age until I felt a throbbing deep up my bum. Finally I felt him unloading inside me. He slowly withdrew; not a word was said between us, and he just turned over and went to sleep. I lay awake a long time, thinking; I was sure it was really wrong, what had just happened. Already struggling with the fear I might be gay, or queer as it was called those days but never having actually done anything with a man I hadn’t enjoyed this first time up the bum one bit. It had felt painful and degrading and if this was what being gay was like I really didn't want it. We never spoke of it next day either and toyed with the idea of just pulling out of the sharing arrangement, but decided to stay on, hoping what had happened that night was just a one-off. It turned out not to be; he was to put it up me every night from then on for the two years we shared together, and weekend daytimes too. It was to become easier though I'd say I got to tolerate rather than enjoy it, but we're talking here about the first time, so that's what I've written about, as honestly as I can remember it after so many years, hoping my experience might help other first timers to know what to expect.

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so you got bumfucked every nite for 2 years ?

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That's right, he never missed a night. As for me I never really got to actually enjoy it, though missed the routine when the relationship ended. He'd even do it when I had straight friends from my previous life staying overnight, sleeping on a mattress on the floor feet away from us. I was shocked first time one stayed that he couldn't lay off just this once. Though we were quiet doing it, I was sure they'd realise from the movement of the bedclothes what was going on. I'm sure they did as though nothing was ever said after, I never heard from any of them again, no doubt disgusted that the regular guy they'd once known had become a queer.

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no doubt.

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Hi there , I was curious.... if he penetrated you every night for the two years you shared together and never once asked you if you wanted to get screwed, then how did it happen "weekend daytimes too" ??
I'm guessing when you were in bed the position you were in was on your sides more like spooning, but these daytime ********, what position where you placed in?

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For these daytime sessions I was placed on my back with my legs in the air either side of his shoulders while he entered me from the front, as opposed to the rear, spooning position he used at night. I was done every weekend daytime this way, holiday daytimes too. He’d just say when he felt like doing it, never ask if I did too, just expect me to get myself ready, lie on my back on the bed, spread my legs and get screwed.

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Further to my previous reply, my memory has been jogged on this and I recall that the first time I was penetrated was actually lying on my back just before my first time being bum-****** in bed. My room-mate had already seduced me through the preliminaries of gay sex, hand jobs, blow jobs etc when he casually asked if he could "put it up my bum". Curious, I let him try; lying on my back as I've described. The first insertion hurt like hell, so I made him pull out and he appeared to forget about it, until that night he took me properly from behind in bed. Now properly "broken in" next time he tried it with me on my back I was able to tolerate that too and my conversion to his regular gay bottom was complete.

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I've done anal to others on many occasions but I'm 58 years old and found myself on the receiving end recently and it was fantastic , it wasn't as sore as I thought it would be I've tried ****** and butt plugs before but the real thing is far superior , driving home afterwards I felt like a naughty girl giggling with joy while his *** was leaking from my *** soaking my knickers, I cant wait for the next time

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my first time was just a year ago. i had just turned 15. this is when i was still unsure of my sexuality. i was over his house and both his parents were away on vacation. we got bored and started doing dares haha. he dared me to kiss him, so i did, but it was so much more then a kiss. he stuck his tounge in my mouth and i tasted his warm breath. i remember it tasted like the fruit punch rockstar, my favorite flavor haha. wile making out i got a *****, which was obviouse through my tight shorts. he noticed to and began stroking it through my pants. then he continued to pull my shorts down just far enough for my **** to come out. he continued to stroke it, . and then leaned in and started sucking it. it felt amazing and i jizzed in his mouth. then, i proceded to pull my shorts all the way off. he said he would be right back, and then returned with a bottle if lube. i took it from his and slathered his **** with it, after making out a little more i leaned over the arm rest of the coutch. he rubbed and prodded my *** hole with the head of his 8.5 inch ****, and then suddenly shoved it in. it was a rush of pain and excitement all in one. wile still inside of me, he leaner in and wispered "are you ok?" i replied "it hurts" he asked if i wanted to stop but i said no and we continued. he started off nice and slow and after the first minute the pain was replaced with pure pleasure. right before he was about to reach climax, he pulled out. i could tell i wasnt his first. we then went into his bedroom, and i layed down **** up on the bed. he asked if he could take a turn. i said yes but i dont know what to do. he said it was ok and he would take control, without so much as a drop of lubricant he mounted me and began bouncing up and down on my 7 inch ****. it felt amazing. since i had already *** in his mouth earlier, it took nearly an hour to *** again, however he never stopped. each minute felt better than the last i came. he knew i was about to *** because right before he went down hard as he could so that every last bit of my pulsing **** was in his ***. we made out a little more and i said "but you never came" "he asked if i wanted ti change that and i agreed imediatly, without re lubing, he put his armsbunder my legs and lift so that my *** was slightly over the bed. he then proseded to pump in and out vigerously. he only put a few inches at first until i begged him to **** me harder and told him i wanted every inche. after what seemed like a blissful eternity he gave on final thrust and pushed as far in as possible. he came so much the it began to seep out of my *** around his still throbbing ****. i will never have any intercource with any man or woman as great as that

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I had always been curious about gay anal sex. I went to a gay bath house in Chicago and hooked up with a young guy there. I ended up sucking him off and he had the sweetest tasting *** I have ever tasted. I swear it was like his diet must have been pure sugar. I asked him to suck me. He was lousy at giving head. He was really rough, lots of teeth and violent motions up and down my ****. I tried to get him to not use his teeth and he just said, "Well, that's the way I do it." I wanted to suck him again and he said he would not be able to get off a second time that way, but he wanted to **** me. I finally agreed. His **** was not very thick and was probably perfect for the first anal **** of my life. I had a little container of lube and greased my *******. His **** slipped in with little trouble. I ws surprised there was little pain, just the pressure of his **** slipping past the entrance. Then it felt good. I was face down on the bunk and he was on top of me. I remember how good it felt to have a **** in me and to have his weight on top of me. I liked the experience, the way it felt with his **** inside of me, but I didn't especially like him. I was disappointed that I could not feel his ***. I thought I would feel the hot *** inside me, but that did not happen. I would love to have it happen again with me on my back with my knees pulled up so I can watch my partners face and kiss while he **** inside me.<br />
jayvee696969

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I had been to see this man to get spanked 3 times then on the fourth I had anal sex.<br />
The first time I went to see him I got there feeling nervous, we discussed how the it will go then we started. First I was spanked on my jeans then I remove these to be spanked on my boxer shorts, a few more spanks he pulls these down to spank my bare bum then told me to *****. After he finished spanking me, I was still naked (he was still dressed) and we sat down and talked about how it went, while we were talking he said I had a lovely arse and **** and he would like to touch me sexually if I visited him again.<br />
The next time I visited we talked and I agreed to be played with, even at 39 I hadn't really been touched by anyone else that way so I would give it a try. The punishment went the same way as before with him spanking me on my jeans then being told to remove them and spanked on boxers but this time when he pulled down my boxers he felt my bum and balls which got me hard. Then when I was told to ***** he wanked me a bit before he undressed and asked me to **** him then he spanked me some more. After a good spanking we sat down (both naked this time) and chatted again about how I felt about what he had done to me, he said he would like to do a bit more with me next time if I agreed.<br />
The third time I visited we discussed what I would be happy with he asked if he could finger me I said I would give it a go. Again I was spanked on jeans then boxers over his knee then he pulled down my boxers and he slid a lubed finger into my arse this gave me a great hard on he then spanked me again. then he told me to ***** and bend over so he could use the strap across my naked bum, he asked if I had ever used a butt plug. I hadn't and he asked if I would like to try one which I agreed to, he lubed it up and told me to bend over and spread my legs, he reached between my legs and gently wanked me as he slowly slid the butt plug in which I found humiliating (which is what I like best about a spanking) and very exciting giving me a huge hard on. Again we sat naked talking about the session and he said that he would love to **** me next time.<br />
The time came last summer when I visited him again we had talked through what would happen before the day and he asked if he could **** me, I thought to myself I might give it a go and say I will but only with a condom and if I say stop it means stop which he agrees with. I arrive at his punishment room and this time instead of being spanked on jeans etc he just tells me to ***** and I get spanked naked with a butt plug in. Then he says he wants to **** me and to lay on floor face down he lubes my arse then gets on top and slides his **** in me he ***** me for about a min then pulls out and tells me to kneel and **** off while he canes me after a bit I say "I'm cuming" he tells me not to stop and canes harder, I hold on for about 10 more strokes of cane wanking steadily then shoot a large load on the towel on the floor.<br />
I want it

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I was alone with a friend watching TV. I was really horny and was wearing these pajamas that made my *** look and feel really good. I took off my shirt and laid on my stomach on the sofa. I could see from the corner of my eye that he was checking out my body. He got up and went to the bathroom and then he came up behind me and started massaging and spanking my *** like crazy. It felt wonderful. He was spanking lightly and feeling my round butt cheeks through my PJs. Then he pulled them down and rubbed my bare ***. I just laid there and enjoyed it. He laid on my back and rubbed on me for a bit then sat on my legs and pulled out a condom and asked if I had any lube. I was so excited knowing I was about to get ******. I told him where to find lube in the bathroom. He got it, greased himself up and laid on my back again while he rubbed and felt my arms and body. It drove me nuts and I just laid there on my stomach and enjoyed it all. Then he lubed me up with a finger and then slid his **** in. I had to concentrate on relaxing. He wasn't really huge and it felt great. Better than anything. He ****** me really good and I was flat on my stomach the whole time with him laying on my back. It was the best feeling I'd ever had. I was trying to seduce him and it worked! I was 17 years old.

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Nice story - I know the feeing and it can be wonderful.
jayvee696969

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i think i could feel his **** still ******* my *** for hours, and it was great. i still love the feeling of a guy shooting his load deep in my loins and still do today

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