tagFirst TimeDorothy and Me

Dorothy and Me

byerotiquill©

England, 1964: I was 18 years old and living at home with my parents. When my girlfriend and I fooled around I played with her tits and pussy and she wanked me off but that's as far as it went so I was still a virgin. My endowment was very generous and I produced lots semen in those days and my girlfriend enjoyed seeing it spurt all over the place. Like all teenage boys I lusted after lots of women but there was one woman in particular who occupied my thoughts more than any other and was the subject of most of my masturbatory fantasies. Her name was Dorothy, although everyone called her Dot. She lived two houses away and I would guess she was in her late thirties, married and had three kids. She was not obese but voluptuous, with very large breasts and a beautiful ass. Although not pretty, she held a raunchy, sexual magnetism for me and I so wanted to fuck her. She often came for a cup of tea with my Mom and I furtively leered at her legs and tits as she sat at the kitchen table imagining all the things I would like to do with her. She would often catch me staring and I wanted to believe she had allowed her skirt to ride up on purpose so I could see more of her thighs. I fantasized about what she would look like naked and how I would maul her huge breasts and bury my face in the massive mounds of flesh. I dreamt of spreading her legs and seeing her hairy pussy, wet and open for me to do what ever I wanted to it with my tongue, fingers and cock. I wanted to lick her entire body and splash cum inside her and all over her. I imagined her on her hands and knees, her huge tits squashed against the floor as I knelt behind her fondling her big, beautiful ass and fingering pussy before sliding my big cock into her.

She had a birthday party for her husband, Billy, in April of that year. Their house was packed with people and as the evening wore on there was much celebrating. Dot looked very sexy in a tight, red mini dress and high heels that showed off her curvy body, shapely legs and large bust. She wore more make-up than usual which made her raw sexuality even greater to my eyes. I stole glances all night and had a hard-on most of the time lusting after her. That's the down side of a large endowment, it's difficult, not to mention uncomfortable, to hide when in public. Billy staggered off to bed around midnight, very drunk, triggering the departure of many guests, including my parents. By 1:00 a.m. there were about ten of us left and I got to slow dance with Dot. She had shed her high heels by then and was 3-4 inches shorter than me. I will forever associate the song with that dance; it was the Everly Brothers, All I Have To Do Is Dream. If only she knew the dreams I had of her. She snuggled into my neck and I never wanted it to end. She must have felt my erection pushing against her but did and said nothing.

By 1:45 I was the only guest remaining and offered to help her clean up the mess left by the forty or so revellers. She began to wash up as I collected the debris and delivered it to the sink. Each time I walked into the kitchen I stared at her arse and wanted to push into her from behind, rub my erection over her bottom and maul her huge tits. I felt a definite sexual tension when close to her and wondered if she felt the same. Several times I almost grabbed her then chickened out as my teenage doubts overcame me. Having collected everything for washing, I picked up a tea towel and began drying. Just being next to her was thrilling; my heart raced and my nerves were on edge. From time to time she would jerk her head back throwing the hair from her eyes and she would glance my way when she did it. My cock was straining against my pants and when our hands touched briefly my breathing increased because she did not pull away. I had to do something even if my advances were rejected out of hand but I sensed that she was as sexually aroused as I was. I grabbed her hand and gently rubbed my thumb across it. She turned and looked up at me and her lips parted slightly. I leaned over, kissed her and held her close. I could feel her tits pushing into me and our tongues battled furiously as our excitement escalated at warp speed. My thoughts were out of control as my hands grabbed and squeezed her ample buttocks and my cock was throbbing violently. We groped each other in a frenzy of sexual excitement.

'I want you,' she whispered breathlessly into my ear, 'I've wanted you for a long time.'

'And I want you so bad,' I gasped.

'I know, I've seen the bulge in your pants when I have tea with your Mom. Let's go on the couch.'

She took my hand and led me into the living room and we sat on the couch. We continued kissing as my hand fondled her tits and she rubbed my crotch. I moved my hand between her legs and felt along her inner thighs to her pussy. She was wearing panties and pantyhose so I didn't feel much except heat which only fuelled my imagination. 'We shouldn't be doing this,' she panted.'

'Yes we should,' I replied and rubbed her pussy harder.

My firm reply and even firmer hand on her pussy seemed to convince her and she said, 'Let me,' and pushed me back into the couch. Her hands went to my zip and she quickly got my cock out. 'Oh it's big; I knew it must be, I've seen your pants bulge so many times.' Her hand wrapped around my cock and after only a few jerks I shot my load over her dress, me, the couch and onto the wall behind. She seemed surprised by the amount of cum and my orgasm was more intense than when I was with my girlfriend. As my excitement abated she sensed my disappointment and embarrassment and calmly assured me that it was alright, that she understood I was so excited, "Cheer up, let's finish the washing up and give it time," she said.

'Do you mean you want there to be another time?' I asked anxiously.

'Oh yes, and it will be much better, I promise,' and she kissed me and we went back into the kitchen.

I felt awful as I dried the glasses and dishes then emptied the ash trays and did a general tidy of the living room. "I guess I had better be going," I said dejectedly and headed for the front door. We kissed passionately then I opened the door and went home. I lay in bed unable to sleep still angry with myself but also excited about what had happened and the prospect of seeing Dot again. I got a tremendous erection thinking about her and jerk myself to another big ejaculation that I contained in several tissues.

During the next several weeks we saw each often but never had the opportunity to be alone. I continued to wank a lot thinking of that first time with her and she was always the subject of my fantasy when my girlfriend did it for me. It was not until late June that the chance for us to be together arose. Billy was taking the kids by train for a week-long visit to his parents who lived on the South coast on Saturday morning. Dot had never gotten along with his parents and never went on this annual excursion. I booked the week off as vacation and we arranged that I would come to her house around 4 that afternoon. It was the longest Saturday mornings of my life. I waited until the street was quiet then hurried down to her house. She let me in immediately and I could see that she had dressed up for me. Her mini skirt was really short and her heels very high. The top two or three buttons of her blouse were undone revealing a lot of cleavage and she had make-up on that made her look even sexier. I think she was trying to make herself look younger for me but I was still very aroused that she was an older, married woman with kids. As soon as the front door closed we were kissing feverishly, my hands fondling her ass. She broke away and walked down the hall and into the living room. I told how great she looked and she blushed, I don't think she got many compliments from Billy.

As before, we sat on the couch kissing and fondling. My cock was ready to burst through my pants and it ached. I squeezed her tits and was dying to see them and the rest of her naked. My hand was between her legs and as I travelled up her thighs I realized she wasn't wearing pantyhose but stockings. I lingered at the stocking tops and felt her warm, soft flesh then moved on to her pussy. I could feel the springiness of her pubic hair beneath her panties and I slid a finger between her labia that felt the moist material. She sensed I was very excited and said, 'Slow down, slow down love, we have lots of time. Stand up for me, just over there,' and pointed to a spot about six feet from the couch. 'Take off your clothes, I want to watch you then you can watch me.'

I hurried out of my things and stood naked before her. My big cock was so hard that it throbbed almost painfully and I thought I might ejaculate without touching it. Dot looked at me then began to play with her tits. 'You have such a nice cock,' she said and undid the rest of the buttons of her blouse and threw it to one side. The bra came next and I saw her magnificent tits for the first time. They were huge, with small areoles and large nipples. I reached for my throbbing cock but she said, 'No, don't touch it, just watch.'

I did as I was told and she stood up, turned around and knelt on the couch. Her skirt was just below her ass and I could see her stocking tops and garters. It looked incredibly horny and I have been turned on by women dressed like this ever since. She wiggled her beautiful ass about then hiked her skirt up over her hips, my heart raced as her hand ran over her pussy and backside. She sat back down, removed her panties and spread her legs. The sight was incredibly horny and I will never forget it and sometimes masturbate to it now. She lay there mauling her massive tits, the dark pubes set against her white thighs and tummy and her pussy lips slightly apart. I stood transfixed, it was an unbelievably erotic sight, all of my teenage fantasies just a few feet away. This mature, horny woman I had craved for almost naked and wanting me to fuck her. I couldn't really believe it was happening and didn't know what I should do next.

'Come here,' she said and I went over to her in a daze. 'Kneel down between by legs.' She played with her tits, pushing them up to her mouth, licking and biting the nipples. 'Feel my pussy,' Dot breathed and my trembling hands ventured over her bush and onto her clit. I was quite skilled with my hands as I had a lot of practice with my girlfriend and as one hand stimulated her clit, the other parted her labia and probed inside. She felt different to my girlfriend, whether it was my imagination or not I'm not sure but her pussy felt hotter, wetter and much hornier. She began to respond to my fingers by gyrating her hips and forcing her pussy onto them, moaning and squeezing her tits. Soon she cried for me to fuck her. This was a moment of mixed emotions for my, I wanted to fuck her desperately but was concerned about my performance. She pulled me on top of her and directed my cock inside. I pumped in and out only about 6 times then shot a huge load that spilled from her onto the floor.

Again I felt inadequate but Dot assured me it only get better and not to worry. We stayed on the couch kissing and fondling. This woman excited me so much that my cock soon began to stiffen in her hand. She skilfully brought my cock to peak hardness as I played with her then she said, 'Let's go to bed.'

I followed her down the hall and up the stairs. What an erotic sight it was to watch her walk in front of me in just a garter belt, stockings and high heels. Her ass was perfection and her big tits swayed to and fro. On the stairs her pussy lips moved provocatively with each step and to this day it remains one of the sexiest things a woman can do for me.

We lay on the bed and she rolled on top of me. Her mouth enveloped my cock and she positioned her pussy above my face. As her mouth and tongue sent wonderful sensations through my erection I spread her cheeks and gazed at her anus and pussy. Almost all of what happened this afternoon had been new to me and the excitement was intense. She was the first woman who had given herself completely to me and it was thrilling. I spread her pussy lips and tasted her for the first time then my tongue explored her anal region then back to her pussy. I loved the taste and my cock throbbed from her attention. She rolled off me, 'You have such a nice big cock, fuck me,' and she opened her legs wide. I lasted much longer this time and she screamed a lot as I rammed into her. I shuddered to an orgasm and we lay still for a long time, my cock still pulsing inside her as it slowly softened.

I spent several hours each day in her house until Billy and the kids returned on the following Saturday afternoon. I had told my parents that I staying over at a friends' on Friday evening but I spent the night with Dot. We made love off and on throughout the night and well into the morning when I left out the back door and returned home. Dot introduced me to many new experiences that fantastic week; sex in the bath, anal and every position we could get ourselves into. I lost count of how many times I ejaculated; she made me so horny it was indescribable. It was the best sex of my life and I will never forget it.

It was difficult for us to meet for the next little while, when I was available Billy or the kids were home. If I was home when she came to have tea and a chat with my Mom we would flash sexual innuendoes at each other when Mom wasn't looking. She would lick her lips seductively or spread her legs as she sat at the kitchen table allowing me to see up her short skirt. I would grab my crotch, accentuating my erection under my pants and once even took it out and shook it at her.

I had a new girlfriend by this time and we were screwing about twice a week and I always thought of Dot and the week we had shared. I did manage to see Dot a few times over the next several months. It was in New Year that she told me the news. There had been much discussion between her and Billy over the last few months about what was wrong with their marriage and what to do about it. Dot wanted to continue having sex with me but realised I would sooner or later move on and besides, she wanted to keep her family together if at all possible. Billy had promised to curb his drinking and pay more attention to the family. They had decided to make a completely fresh start in South Africa and would be emigrating in three months. It was a bit of a shock but I got used to it and thought it would probably be the best thing for them. We fucked like crazy when the very few opportunities arose and then she was gone.

I remember Dot fondly to this day. She was a sexy, horny, sensual, mature woman who had a major influence on shaping my future sex life in the following ways:

-I prefer women with a bit of meat on their bones rather than the rail-thin models that abound today.

-Big, natural tits over fake, silicon jobs any day.

-Women dressed in heels, stockings, garter belts and other sexy clothing and watching one walk up stairs dressed like that is still the most erotic sight for me and always brings on a powerful erection.

-I love playing with a woman's arse and pussy while she waits to be fucked doggy-style.

-A soapy sex partner is still a thrill.

The odd scrap of news filtered back from South Africa for the first few months. Dot had her fourth child after about eight months and I often wonder if it is mine, I was certainly fucking her a lot more than Billy. The last news we had reported that Billy had suffered a fatal heart attack. I never heard from Dot again.

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