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anal discipline stories
Several Firsts
By: Elusive Lady (an_elusive_lady@hotmail.com)Tony was married. I knew he was married. That didn’t stop me from talking about sex with him, making vague broken plans to meet him, etc. I hadn’t seen any pictures of him nor had he seen any pictures of me. He was just Tony with a bunch of numbers after his name, and of course, I was known as the Elusive_Lady to him. I never stand to make a screen name with a bunch of numbers. He knew I was thirty and had spent the greater part of the last 7 years living a celibate sexless life. I was tired of that lifestyle and was wishing for a change. I was never very good at masturbation, and when I would get all hot and bothered by the online chats, I would end up going to sleep all turned on and with nobody to relieve my needs. I wasn’t a virgin, but I had never had an orgasm in my life, and I knew I was missing out.
One day I was cleaning house and I heard the bell ring. Standing there on the doorstep was a man I didn’t recognize.
He was taller than me and had very broad shoulders and a bit of a paunch. Balding with faded red hair and freckles. I was self-conscious because I was wearing an old red cotton dress that I sometimes wore when cleaning the house. The curves of my large-figured bodies were evident, especially since I wasn’t wearing anything underneath the dress. I wondered how elusive you really were, said this stranger standing on my doorstep.
Tony? I said, disbelieving, and he grinned and I knew it was him. I invited him to come in as I had to finish my cleaning! He followed me up the stairs and into my bedroom.
He sat on the couch and we chatted as I finished cleaning up.
I wanted the apartment to be in tip-top shape, and since I got into the mood to clean the apartment so rarely, I wanted to finish while I was still in the mood. After the last bit was done I flopped onto the loveseat across from Tony and looked at him. He wasn’t looking at my face, however, his eyes were on my breasts, clearly delineated by the old threadbare cotton cloth of my dress. I felt self conscious and asked if he didn’t mind waiting while I took a shower and cleaned up. My hair was all frizzy and in a ponytail, and I was dirty from a long day. He seemed amenable and I went into my large bathroom to have that shower.
I had just finished washing my hair and was preparing to wash off the suds, when I heard my shower curtain pull back. I knew without asking what was going on. Tony had joined me. With the shampoo rinsed out of my hair I looked at him. He wasn’t any more impressive naked than he had been clothed. But I had been horny for seven years and didn’t feel like blowing off this opportunity. I handed him the soap and instructed him to wash me. I stood near the back of the tub and he stood under the flow of the water and started to lather my whole body. The feel of his hands on my breasts, buttocks and eventually between my legs was revving me up. I wanted more but wasn’t sure if I would have the courage to ask or even agree if he asked, however I needn’t have worried, he wasn’t asking.
bend over so I can wash you good, he instructed. I leaned over, and then over further until I was bent double, my shoulder blades pressed against the back wall, my hands on the edge of the tub. His fingers were stroking me, and I felt his finger probing my vagina and then soaped up and slick, I felt him probing my tight asshole. I was shocked to feel this and was ready to protest. The feel of his fingers on my clit and pressing inside my vagina made me not want to object for fear of making him stop everything he was doing. I relaxed around the finger that was slowly fucking my ass and moaned in desire. Lift your leg, he instructed, guiding my leg so that I had my foot on the edge of the tub.
He pulled his finger out of my accepting anus and I felt the head of his small cock against my vagina. He pushed in, barely stretching my unused pussy, and then he pulled out after only one or two thrusts. Before I could wonder if that was it I could feel him pressing against my anus with his swollen dick. Moments later I was surprised to realize I was being fucked in the ass. Once he felt my acceptance of him he began to thrust inside of me, and fairly quickly he had an orgasm.
When he pulled out I felt somewhat disappointed and also hot to try more. I wanted to really explore that sensual side of my nature that actually enjoyed having my ass fucked. The experience was so brief, his orgasm so quick, that I was left wanting. He told me he would get dressed and wait for me to finish my shower.
I took another ten minutes in the shower once he left the bathroom, thinking long and hard about this newfound facet of my nature that I had only discovered accidentally. I was as frustrated as ever and hadn’t found the release I had expected to find. By the time I was finished with the shower, I was full of plans on the sensual afternoon ahead of me. I was disappointed, of course, to discover that the apartment was empty once I got out of the shower. There was no sign that he had ever been there. Only the slight soreness in my ass to testify that my anal virginity had been taken.
Tony never responded to any emails or communication after that. I wasn’t really that disappointed, his behavior wasn’t worth my time. Not to mention the fact that he left me more frustrated and unsatisfied than I felt before his visit.
My next real-life encounter with someone from the internet as far exceeded my desires and expectations as the previous one had left me wanting.
Another of my fantasies, in addition to my new-found fantasy of having my ass fucked by an expert instead of an insipid wimp, was to experience the feel of a huge black cock inside of me. I’d spent the last seven repressed years of my life in an almost all-white state. Now that I was living in Atlanta my fantasies were alive.
Joe refused to describe himself online, but often referred to himself as a mutt, a combination of black and Hispanic. The ladies never seem to complain about my looks, was the most he would say about himself. I was frank with him, in our late-night discussions about my fantasies. He agreed to call me so we could talk.
In that discussion I was even more candid about what I wanted, and about how I was not sure about my desires. I was not used to this sort of thing. His final words on the phone were, you never know until you try.
I decided then and there that I would do my best to see that my fantasies were fulfilled. He gave me his address and encouraged me to come over. It was more than an hour away, but I was willing.
I almost chickened out on the ride. It was nearly midnight by the time I arrived. The address was a small cookie-cutter house in a newly developed neighborhood. I knocked on the door and my hands were shaking. When he answered the door I was stunned. He was a masterpiece, beautiful! His skin was a rich burnished brown color, his hair tight short-cut curls. His hands were large and matched the muscular build. He was everything I’d ever fantasized about, and more. He smiled when he saw me. I was self conscious because I am a larger woman. My stomach is flat, but I have a large butt and very large breasts. I always thought of myself as fat, even though my stomach showed off how muscular and toned I was.
I just couldn’t fight the genetics that gave me large hips, a big butt, and muscular thighs. On my mother the combination had looked good, but she was 5’8. On my own puny size of 5’2, it just looked fat.
The look of admiration on his face took all thought of my size and beauty or lack thereof from my mind. It’s the Lady, he said, pulling me gently into his home. I looked around and saw a tidy bachelor pad, everything neatly put away, no signs of him being anything other than a generous but tidy man. After the sloppy looks and manners of my last internet date I was happy to see this.
We talked for a while, and he brought me a glass of wine. I started to loosen up and he finally stood and pulled me to my feet.
His full lips came down over mine and I knew in that instant that I had never been kissed. Not really. Not compared to what he could do. He was not only a masterpiece of human beauty, but he was a master artist when it came to sensual things.
I’m dying to see what your beautiful body looks like underneath that outfit, he whispered onto my lips. When he sensed no objection from me he pulled off my black velvet top and then pulled my matching pants down to my feet. He pulled the pants and my short black boots off at the same time. When he was done I stood before him, shyly wondering what he would see.
I knew that he saw the black bra and matching panties, and the ridiculous pair of black lace knee-highs I’d worn. My hair was a nondescript rusty brown color, and my features were unremarkable.
His hands went around behind my back and he unfastened my bra.
That’s what I thought, he said after looking at me for several minutes. a beautiful goddess! he stepped forward and cupped one full breast, rolling the nipple between his fingers as he kissed me again. I could feel that he was emanating a heat from his body and I could tell that my body was reacting to his proximity.
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He backed away and looked at me some more before pulling his teeshirt off and then stepping out of his shorts. Standing naked in front of me he was like a virile god, the size of his shaft making me weak in the knees.I could feel a gush of wetness between my legs at the thought of what he would do with that enormous tool.
He guided me to sit back on his couch and then he knelt in front of me. His fingers worked their magic on my legs while he pulled my stockings off. When he was done with that he leaned forward and buried his mouth and nose in the crotch of my panties. I could feel short hot bursts of his breath coming through the fabric. Finally his hands came up and he peeled my underwear off. We were now both naked, and I wanted to feel his cock. He didn’t move close so I could do that, instead pushing me backwards so I was leaning backwards. His large dark hands spanned my hips and pulled me further towards the edge of the couch and then he parted me and with one lingering lick he shattered all of my preconceptions about pleasure. I was ready to beg him to fuck me at this point.
He seemed to have patience and his touching and sucking on me was bringing me to a frenzy of sensation. I was ready for him to plunge his tool inside of me. Finally I was almost begging him to fuck me, and he moved forward, the huge breadth and length of him opening my pussy wider than it had ever been opened, and plunging deeper as well. His hands went to my ankles and he lifted them and pushed my legs back towards my body so that I was raised up right next to him and ready to receive his full length. I moaned at the feelings building up within me..
Pretty soon I felt as though a warm flood of sensation was stealing over me followed by the most intensely pleasurable sensation of my life. I was moaning deep in my throat in response and then I felt his seed pulsating into me. Both of us were locked together in a frenzy of passion and pleasure. Later when we were lying side by side on the spacious couch, I was thinking of the pleasure we had compared to the ineffective attempts to give me pleasure I’d felt from Tony. Joe won that contest hands down.
After a while lying close Joe stood and went into the bathroom, returning with a towel that he used to lightly clean me up. When he was finished he reached for the wine and poured me another generous helping and then put on a sensual movie. I was just starting to get into the movie when I saw that Joe was hard again. Why don’t you get on your hands and knees, he suggested.
I did so and wondered what would happen next. Feeling his warm hands on me I couldn’t help but shudder in anticipation of the delight that would be mine.
He must have put some sort of oil on his hands because he started to rub my large butt all over, before starting to rub my puckered up hole. I wasn’t sure how I would be able to take his enormous size. I needn’t have worried. His fingers started to probe my anus and then slipped inside. As before it was painful, but only slightly. I felt his large cockhead pressing against me and expected to feel pain. The difficult entry was painful, so much so I was about to tell him to stop.
But two things stopped me, one being that I was relaxing and the pain was dwindling, and the second was that I was getting turned on by his touch. Even through the pain I wanted nothing more than to feel a real cock in my ass. It wasn’t long before he was fucking me with more vigor than before.. I wanted to yell in triumph and to curl my feet up into round balls of pleasure.. His hand on my clit while he pounded my ass had me begin a series of earth-shaking orgasms. I felt overwhelmed by the sensations and knew that this would be one of my favorite sex acts in the future.
Another time, I’ll tell you about what happened when Joe’s roommate came home.
Another of my fantasies was going to be fulfilled that night!
