Billy Helps Me Out

Everybody in this story is over eighteen.

In fact this story begins just after I turned eighteen. I had a lot of goals for myself now that I was legal, at least sexually. I still couldn't rent a car. I very much looked forward to the time when I had a serious boyfriend and wanted to be a good lover. I had several friends who were of age and who had serious lovers and they all now fucked with abandon to the greater glory of God. I was jealous. I knew there was a lot to learn and set about learning it with a vengeance.

Fortunately I knew a lot of boys and was pleased to find out they were more than willing to help me and by the end of the summer I had made a lot of progress. But as Labor Day (an American holiday in the first week of September) approached there was still on glaring deficiency in my sex education. I was an anal virgin. What to do?

I approached my friends Danielle and Kristie, fellow members of our local girls-only BDSM group The Wenches, about which you can read in my story of the same name. Danielle had a steady guy, always did, and she had considerable experience getting it in all her orifices, including her bum. She was blissfully happy with her downward facing experiences and urged me to give anal a try.

Kristie was more lukewarm. She was head horse trainer on the nearby Harrington estate, which employment included getting to live in the little house which became official Wench headquarters. In order to guarantee her continued employment she was obliged to provide certain personal services to the younger Harrington males. And one of these included regularly taking it in her ass. So she had plenty of experience and advice to give, though her participation was from more of a pragmatic than erotic standpoint. Whatever the case, I was determined to try my luck getting it while lying on my tummy.

Kristie helped me implement a program which would allow me, over a two-week period, to train my rectum to accommodate an object the size of a guy's dick. Generously lubed I would, in the privacy of my bedroom, gently insert objects of increasing size into the critical orifice, all while learning to relax and breathe deeply, kind of like one does in yoga, which I enjoy.

She had all the required material. In addition to lube there were these butt plugs that looked for all the world like little Christmas trees, maybe skinny ones, of gradually increasing size. Beside the Christmas trees there were similar things that were wider and had handles on the end, like rings, so I guess they couldn't get stuck in there. Then there were longer ones that were ribbed and that looked more like penises except penises aren't ribbed. I worked hard and made good progress and actually began to like having something stuck up my ass.

Finally there were things that were shaped like dicks with heads on them just like a guy. These were still longer and of a good thickness and that was the final exam, if I could take the longest and fattest of those I would be ready. Kristie said plenty of lube and I'd do just fine. Again I worked hard and made good progress. There was no pain but it was uncomfortable at first, especially getting the head inside me at the start.

But I had to get past that and get them all the way in and after some trying I did and once in they felt better, just like in real life. Lastly, I started moving them in and out, getting up a head of steam with faster and faster strokes like a boy would, and it felt good and introduced the possibility that if I could get relaxed and concentrate on my feelings I might be able actually to cum. I felt I was ready to try it with a boy.

The following Saturday night I repaired to The Spotted Cow with Billy Andrade for beers. I was of course too young to drink, but The Cow was quite liberal admitting women, especially if you had a decent rack, which I did. I admitted to Billy that I had mixed emotions about anal. I must say the thought of a guy putting his dick in my soft white bottom filled me with apprehension.

But he offered encouragement and agreed, quite readily I thought, to help me get started. He suggested we go to his place where I would strip naked and be bound tightly with rope, to prevent any last minute reservations. I would then be bent over a table, properly oiled up, and experience what he promised would be an eye-opening experience. I was not particularly surprised he felt that way. I agreed, we had one more round at The Cow and then, suitably relaxed, we headed for Billy's.

We arrived at the Andrade digs to find his parents at home watching TV. They greeted me warmly, always glad to see me with Billy because they considered me a suitable candidate for a daughter-in-law. His mother complimented me on my outfit, unaware I was about to remove it out in their carriage house and allow myself to be bound nude and bent over a table. And so it happened, we went out back, upstairs into the dining room and I busied myself getting naked while Billy got out the ropes and lube and arranged the dining room table for this somewhat unorthodox purpose. He complimented me politely on my naked body.

He moved quickly. He had me put my hands behind me. He bound my wrists together tightly and ran the free end of the rope around my belly completely to anchor my hands up high enough so I would not be able to interfere with the proceedings further down. He arranged a comforter from the bed on the table-top for me to lie on. He pushed me down on the table-top and bound me to it. Tightly.

I couldn't move my upper body. My lily-white bottom was perfectly positioned for what was to be done. He stripped below the waist. He was hung like Secretariat and I began to get a little uneasy about what it would feel like to have him in me.

Billy took up a position behind me. I felt his finger at my asshole, cool with the lube. He inserted the first joint of two fingers and began working them into me. I cringed but I tried not to resist. Relax and breathe, right? So far, so good, the fingers went in easily. My preparation was paying off. He alternated putting his fingers in, well lubed, moving them around inside me and coming back out for more lube. A little more and finally he had his whole middle finger up me. It didn't really hurt but it felt really weird. Then he began to turn the finger slightly and I could really feel it up inside of me.

The next step was two fingers together and this time I could feel my insides being spread more than before and I tried to move but I couldn't. He pressed a little harder and then he was in me all the way with the two fingers. He moved them in and out maybe just halfway and then some more and then further in and out, and I was beginning to get a bit of a feeling of being fucked in the ass.

It felt uncomfortable but good at the same time and I started to move my hips a bit. I could actually maybe see how I could cum by pressing my genitals into the towel underneath me on the table-top. He kept doing it and by the time he stopped I swear I was halfway there. But fingers were one thing and his dick would be another. I knew the hardest part of this would be getting his dick head through my entrance.

By now he was well erect and I knew I had to get ready. I tried to focus on relaxing, breathing, and remembering to bear down to get him in there past the tightness and see how far he could go. Whatever the case with me though, he was ready to stick his dick in. Once more he lubed my asshole and the immediate area inside me liberally. He gave himself a few quick strokes to get it harder and lubed his dick. The softness of my bare bum beckoned, and he moved to take advantage of the situation.

He positioned himself with his dick at the entrance to my bottom. The comforter under me gave him a way to slide his hands up under me up give me a generous feel. He pulled my bare ass up just a little higher in the air off the comforter, bringing his cock up to just the right height to enter me. I trembled a bit, but there was no turning back.

I could feel the head of his cock at my asshole. My heart was racing. He took a deep breath and firmly began to push his hips forward. I tensed a bit and felt the head of his dick begin to enter me. He knew he was hurting me as he pushed himself in, but he didn't stop. My asshole widened enough as his dick head pushed into me. Then the head slipped inside and I began to accept his shaft, doing the best I could take all of it.

He pushed harder and I cried out. Now he was sure he was hurting me, but he kept pushing and pushing and he got further in and then miraculously the going got easier and he wasn't going to quit until he had every inch of himself into me. I bit down on my lower lip against the pain of him getting in, but now with him in me it was better. Then he drew his cock almost out of me and leaned forward and thrust back in, intent on making me get used to taking every inch of him again.

I could feel my whole body tensing up underneath him and my tight little butt clenching onto him, but as he did it more and more easily I started to relax a little and bit by bit I tried to get into a rhythm with him. Now each time he stuck himself into me he no longer tried to get his full length into me. He began pulling back on my hips each time he thrusted and pushed my bum against him.

I figured out what he was trying to do and I began to work my bum to push myself back to meet each of his thrusts, so I could have better control of what I was feeling. He began to run his fingers under me over my tummy up to my tits, squeezing them and pinching my nipples and I started getting hotter and hotter and I knew if I kept trying I could make myself cum.

By now the fucking he was giving me was getting to be enough to push him over the edge. He thrust myself into me half a dozen more times and one last time and suddenly he was there, and he held himself completely inside my ass as he began to cum. Harder and harder he came, and he just emptied himself into my bottom. He pushed again and again and I just screwed my eyes shut and holy shit I'm just about there myself and that was the last thing I noticed as I started to cum.

It just kind of started to happen and I prayed don't stop, don't stop and I can't and I just kind of disappeared into the void and I don't know for how long. I just tried to grind myself harder against the pillow and on and on until I couldn't anymore and it was amazing.

After a while I kind of slowly started to come back down and slowly got more aware of what was happening. Little by little there's the room and the table and I'm tied to it, and he's got his dick in my bum and I can feel my breath still coming hard and finally I'm pretty much all the way back and then I am and it's quiet and finally I felt him take himself out of my bottom.

I lay there panting while he cleaned himself up and got dressed. He cut my ropes enough so I could get myself untied. I just lay there for a while feeling the after effects. My asshole hurt some from his entry and in a way I could still feel the pressure of his dick inside me. I was limp from the exertion of him pumping me and from me having cum. Finally I untied my ropes and wandered in the bathroom and took a shower. The hot water on my body felt good. I had to dry my hair lest his parents see it wet and wonder what we had been doing. Possibly they had an idea, but I imagine they thought we might have been doing it in a more conventional manner. I didn't really know what to make of the whole affair. I guess it was a success. At least now I could say I've been fucked in the ass. If anybody asks.

Billy drove me home and I sat a while and talked to my Dad and then went to bed and slept quite soundly. I still had marks on my wrists from where Billy had tied me so tightly. If my Dad saw them he said nothing.