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The Ladies Of My Life - Part 1 - 1963-1968

"The ladies in my sex life."

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I was born in England in 1946 and emigrated to Canada in 1968. I've had many adventures and experiences in my life including a rich and varied sex life.

I turned seventeen in 1963 but was still woefully lacking in sexual experience but I was an accomplished masturbator. I was sexually attracted to any reasonably attractive female, especially older women many of whom were neighbours. One lady in particular monopolized my wanking fantasies and she lived next door. Her name was Dorothy, 'Dot' to all who knew her, she was married with three kids and I would guess about twenty years older than me. I'd watch her from my bedroom window when she was in the garden. I liked it best when she was hanging washing on the line because she would bend over, causing her short, tight skirt to ride up her thighs giving me glimpses of her panties which, at the time, was the height of eroticism for me. I'd jerk off and splash a large load of cum all over the window.

My sexually-awakening mind would look down at my ejaculation on the window and from my angle it would cover Dot's body and I imagined her lying naked with me standing over her jerking off endless sprays of cum until she was covered from head to toe in a thick, white, messy mass. She monopolized most of my masturbatory fantasies and I probably spilled a gallon of semen thinking about fucking her although I wasn't sure exactly what form that would take but my imagination was very active and vivid. Often, after I cleaned off the window, I'd lie on my bed and within an hour or so I'd jerk off again thinking of her and her voluptuous female body that I lusted so frequently for. I had a girlfriend who was a year older than me who liked to masturbate me and direct my semen over her legs. I'd think of Dot while she jerked me off and always had a big load for her legs and quite often elsewhere.

Dot is responsible for my sexual preferences and fetishes: I love the female body, the soft flesh, the curve of the hips, a garter belt around the waist with the garters snaking over naked thighs to stocking tops, very shorts skirts and high heels, the erotic sway of bottoms, full breasts, hard nipples, the rear view with gorgeous butt cheeks and anus and of course, the pussy whether haired or bared they are all the same yet all so different and the center of a horny guy's universe. I love the creamy feel and taste of pussy juice on the tongue and fingers, the way they moan, whimper, scream, coo and urge you to fuck them when you are pleasing them. I love watching a mature, sexually confident wife being fucked by one or more virile, well-endowed black bulls and enjoying every second, especially so if you are watching your wife. Dot was the beginning of all of this and she has influenced and shaped my sexuality all of my life. I've been very lucky to have been intimate with many sexy, erotic, horny ladies with terrific bodies many of whom have loved to dress erotically for sex and who have enjoyed being fucked by me and other men.

Dot often visited my mom for a chat and a cup of tea and if I was home I leered at her every chance I got with my cock throbbing violently the whole time. I could look into the kitchen and see her in profile as she sat opposite my mom. I wondered what her large breasts looked like and ogled her legs as her short dress or skirt always hiked up a little as she sat and I studied the beautiful curve of her bottom. She knew I stared; I did it all the time when she was around and I'd seen her smile ever so slightly as I caught her glancing at the bulge in my crotch that was impossible for me to hide and I knew she saw the lust in my eyes. There may have been a sexual aura between us, if there was I was too inexperienced to sense it. 

It was nearing Christmas and three months away from my eighteenth birthday when Dot and her husband, Bill, had a party. I knew everyone who was there; they were all friends and neighbours. Sometime after midnight, guests began to leave. Bill had gone to bed after consuming a lot of alcohol and it ended with just Dot and me ostensibly because I wanted to stay around her as long as possible. I helped clean up and offered to dry glasses as she washed them. As we stood at the sink our bodies touched from time to time, just gentle brushes but they were incredibly exciting for me. My cock was ready to burst but I didn't know what to do, should I make a move or not? I felt she was sending me erotic signals but if I had it all wrong I would feel a fool and even if I did make the first move I wasn't sure at all about the second. As it turned out she made the move. We had finished the washing up and I was beginning to panic thinking it was time for me to leave when she asked me to dance. Music had been playing all night but I had not been listening.

Dot wasn't slim by any stretch of the imagination but she wasn't fat, she was a well-built woman with large breasts and a lovely-shaped ass. Her body was perfectly proportioned and I wanted her so badly. Neither was she pretty in the conventional sense, she had a raw, unmistakable raunchy, sensual and sexual appearance. Through my eyes, she always looked ready for sex although I was vague on detail.

Dot was about the same height as me in heels but she kicked them off as we began to dance, it was a slow shuffle more than a dance. My cock pressed into her tummy and she did nothing to change that. I was breathing heavily, it was super erotic just holding her and she said, 'Kiss me.' I hesitated and she got on tiptoe and we kissed. I was emboldened and my hands drifted down onto her bottom and I caressed and squeezed the wonderful mounds of female flesh. 'I know you want me. I want you too. I want to teach you everything,' she whispered.

We kissed and fondled then she said, 'Not here, come.' We made our way outside into the garden. It was after 1:00 AM and very quiet as she led to the garden shed. Bill spent a considerable amount of time there, probably to get away from the noise of the kids and to have some 'me time.' There was a large, overstuffed brown leather chair and Dot sat in it. She put a finger to her lips, 'Just watch.' She placed her hand on the top button of her blouse and teased it between her thumb and forefinger while all the while looking at me and moving her tongue over her lips in a very erotic way.

My heart pounded, I was frozen to the spot and my cock throbbed violently. Dot undid the button then moved slowly to the next and the next. When all the buttons were undone she slipped the blouse off her shoulders. Her tits were huge and overflowed her bra. Her cleavage looked soft and sensual and my breathing quickened as I anticipated finally seeing what I had dreamed of and masturbated thinking about many times.

Reaching behind, she unclipped her bra but held the cups in place, 'Do you want to see my breasts?' she asked and I just nodded dumbly. 'I've seen you looking at them, I bet you'd love to feel them and kiss them, wouldn't you?' again I just nodded my head. 'Come here,' she whispered and I shuffled over wondering if I would faint before I got to her. 'Take my bra,' she said and my trembling hands ventured forward and pulled it away. Her tits were magnificent and I took a deep gulp of air when she told me to feel them and I tentatively explored the lovely, soft mounds of female flesh. I was in awe but got daring and pinched her nipples and she murmured, 'Oh yes, that's a good boy.' She hiked up her skirt and I gazed at her stockings, garter straps, naked thighs and white, silky panties with wisps of dark pubic hair sneaking out on either side.

She unzipped my pants and pulled them down, 'No wonder I've seen the bulge in your pants so many times, you have a nice big cock and it's so hard,' she murmured.

'It's nine inches when hard, I've measured it,' I blurted, not knowing why I said it.

'I bet it is, it's lovely,' she replied and wrapped a hand around it. She gave it a couple of tugs and I exploded all over her tits and face. I had three overwhelming emotions as I stared down at her body now splattered with thick streaks of my semen; embarrassment at my total lack of experience, my almost non-existent knowledge of sex and disappointment that I had cum so quickly. We had no internet when I was growing up and we all learned from peers but unfortunately, most of it was myth, mystery and legend.

'I can see I'm going to need to give you a lot of lessons,' she said with a soft laugh and licked a large glob of semen from her lips into her mouth, 'Umm, you taste good!'

'I've got lots more of that,' I stammered.

'I'm glad and I want it all, although not only over my tits and face, I want you to put it in my pussy, now take my panties off.'

I knelt between her thighs as she gathered more cum with her fingers from her tits and put it in her mouth. I took hold of her panties and gently pulled them down as she wriggled to help the operation and I got my first look at her mature pussy. Although my mind was in a fog I remember wondering how many cocks had she enjoyed in there, lots I imagined. It struck me that cocks had fucked her since I was a baby and now I was going to fuck her mature, well-used cunt with my virgin cock. It was all overwhelmingly exciting!

My unabashed lust for her was the only thing that stopped me from running out of the shed. Dot could see my embarrassment and disappointment and said, 'It's alright, it's alright, it's perfectly normal and it will get better for you, I promise. I'm going to teach you how to fuck me but first I want you to eat my pussy.' She then rubbed my cum all over her tits and put her fingers in her mouth again.

Dot spread her pussy and guided my tongue to her clit and gave me instructions. She ran her fingers through my hair and moaned quietly and I felt my cock rapidly stiffening. She pulled me up and kissed me passionately and I felt my erection pressing against her. 'Oh, hard again already, I like that, you are a horny boy, aren't you?' and she steered me inside her. I probably lasted all of two minutes but it was the best two minutes of my life so far. 

It wasn't easy for us to get together and I masturbated a lot thinking of that short time we had together. It was probably three weeks later when she was hanging laundry on the line that I went out into the garden, leaned on the fence and said hi. She said she hoped she would see me and told me why. Bill, who was a toolmaker, was going to Northern Ireland to set up some new tools. He was leaving on Sunday and was expected to be away for at least a week. The stars had aligned! I was on a College break the following week which meant I was available every day.

I lived with my parents and it was no surprise to them when I told them I was going out that night, I often went out when they were thinking about going to bed. A little after 9:30 PM on Sunday I went through the back door which Dot had left open. She was in the kitchen and we embraced and within seconds were frantically kissing and fondling. She told me that Bill was away for nine days and during that time we fucked like rabbits. During the week, when the kids were in school, we spent all day enjoying each other's bodies. Dot always wore something erotic and we fucked in every possible position. She was an excellent teacher and in those nine days, she made me into a proficient, if still novice, lover. She was draining me of cum but I did a decent job of giving her at least one load every day. I splashed lots in her pussy but also down her throat, over her face, tits and ass.

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It was difficult for Dot and me to get together for several reasons; she had three kids, she lived next door so, though that was convenient, we needed to be careful and not raise suspicion but we got together every chance we had. I learned fast and was fucking her at every opportunity all over the house and in the shed where we made good use of the old leather chair fucking in every conceivable position on it, I loved to bend her over the back of it and give it to her really hard and deep. I believe I must have explored every square inch of her body with my tongue as well as my fingers and I loved all of it, even her asshole. She was a great cocksucker and I loved to jerk my load into her mouth, face, tits and any other part of her body. Fucking her from behind was a dream, I loved looking down at her ass and my cock sliding in and out of her cunt. I thought then as I was to think in the years to come that I was looking at my cock pumping into a married woman's pussy where other cocks had been. She sometimes wanted me to cum over her asshole and lick it up which I did gladly.

She told me that Bill wasn't much interested in sex anymore and hardly ever touched her. I couldn't fathom that and thought if she were my wife I'd be fucking her multiple times every day - such is the naivety of youth.

Dot got a job with a local bookmaker and he was soo fucking her. They would stop on the way back from the races and fuck in his car. He'd drop her off at home in the drive at the back of the house and I'd watch her walk up the path with a mix of jealousy and arousal knowing another cock had just been in her hands, mouth and pussy. She always looked up to my bedroom and only once was I able to go over right after she arrived home. I could smell his aftershave on her and taste his cum in her mouth and pussy and the jealousy disappeared and there was only arousal. She said he was kind to her and he never lasted very long and it made him very generous. It was then that I began to think of Dot as my mature slut and that was highly arousing.

I thought a lot about her with other men, of watching her being fucked and joining in. I told her about this one day and she gazed at me for several seconds before saying wistfully, 'I've been fucked by a lot of men. There was a time,' she stopped and went to the bedroom dresser and returned with a large brown envelope. 'There was a time, before the kids, that Bill was very much interested in sex and especially watching me with other men. We used to go to a club that catered mainly to folks from the Caribbean. We liked the music and the atmosphere and the people were very friendly. I had always been attracted to black men and . . . well, you'll see,' and she tapped the envelope.

I opened it and took out its contents. There were about a couple hundred 4x6, black and white photographs of a younger Dot being fucked by various black men. In some she was with one man, in others there were several enjoying different parts of her body with hands, mouths and cocks while other men stood around with erections waiting their turn to fuck her. I couldn't believe it, I had never seen anything close to this and I was immediately engrossed and highly aroused by it. 'Bill took all the photos,' Dot said, 'he loved to watch me being fucked by black men and there were lots of black men who wanted and did fuck me and I loved it.

We went to the club every week and we would go to someone's house. As the word got around and the number of men grew but there were other women who came along, white women who liked black men and black cocks. Don't believe all that you hear, not all black men have huge cocks although some do and I've enjoyed my share as you'll see.' I went through the photos and saw several women with Dot being fucked, on their backs, hands and knees and on top. I lingered over the ones featuring Dot and wished I could have been there and seen it live. My love of interracial sex was born.

Britain in the mid-1960s was vastly different to North America. There were no motels and hotels were used only by business people and those having affairs so I guess Dot and I fitted into the latter but I'd never stayed at a hotel. I used to have an occasional bet on the horses, I didn't win often and never very big except one time and it was from the bookmaker who was fucking Dot. I won just over 300 pounds and knew what I wanted to do. I discussed it with Dot and she was very excited to do it and would think of a way to make it happen. With the help of a sympathetic friend, Dot was able to tell Bill she was going out with that friend and staying overnight at her place. It was no problem for me, I'd just tell my folks I was going to a party and they wouldn't expect to see me until they saw me.

We chose the newest hotel in the city called 'The Albany.' Because we needed to be discreet, Dot went in by herself and got the room then came outside and told me the number. She insisted I wait at least forty-five minutes before coming up and it was the longest forty-five minutes of my life but it was worth it.

I had never seen a woman looking more sexy and erotic than she looked when she opened the door of room 448. She had fixed her hair in a different style and was wearing more make-up than usual. Her white blouse was undone halfway and her large braless breasts were spilling out in a most erotic way. The black mini-skirt was so short I could see her stocking tops and garter straps and the spike heels made her taller than me, which was very horny. She turned and bent over and I saw she was wearing open-crotch panties. To my eyes, it's still the horniest way a woman can dress for sex and I definitely have a fetish for those clothes on a woman to this day.

Dot closed the door and we embraced immediately, kissing feverishly as I fondled her ass. 'You look incredibly sexy, let me look at you,' I said and sat in the only chair in the room. She paraded about, moving her hands over her breasts and bottom, bending over and generally behaving like a slut that I loved so much. As she was cavorting, I was getting out of my clothes as best I could from my seat. When I was naked, I spread my legs and displayed my throbbing cock to my horny, erotic, mature, married slut woman. It was the first time I had slept with a woman, although there was not a lot of sleeping achieved that night! We fucked for hours in every place and position in the room including the bath. It was beyond horny to play with her soapy tits, ass and cunt. We just lay cuddling, fondling and I wanted it to last forever. We left separately in the morning after having sex and continued to get together whenever we could, in her home, the shed or in the fields near our homes.

In August 1967, we were lying in bed after satisfying our lust and I sensed a sadness in her. I asked what was wrong and she gave me the bad news. Her husband, Bill, had sworn off the booze and wished to revitalize their marriage. He wanted a fresh start for the family and had been considering moving to South Africa. Dot thought it would never materialize but it had and they were emigrating. She hugged me tightly and through tears said, 'If not for the kids . . .' but she never finished the sentence.

We had an intense end to our relationship. Bill went to South Africa first and Dot and the kids followed when he was settled. The sex was terrific and frequent during those final weeks, it felt like we had to get as much of each other as possible before the inevitable end but it was difficult with the kids around. We devised plans to try and meet two or three times a week or more if possible. We'd meet in a nearby woodlot and on a golf course at night where Dot would bend over a fallen tree trunk and I'd lift her skirt and give it to her from behind. I also took the odd day off from College and we'd fuck all day while the kids were at school.

I felt a great loss after Dot left, I missed her body, I missed the sex; especially I missed her bouncing up and down on my cock, her gorgeous big tits enveloping my face while I fondled her bottom and I missed looking at that bottom and her pussy as I fucked her from behind. Most of all I missed her. She gave me the confidence and skills to sexually please a woman and influenced my entire sexual life and for that, I am eternally grateful. I received a handful of letters from her one announcing she was pregnant and was certain it was mine but things were much better between Bill and herself, they were having sex so he would believe it was his and I was not to worry.

At the time the news didn't have a powerful impact on me. I was happy to have fucked such a sexy woman twenty-plus years older than myself who'd influenced my sexual fetishes all my life. The last line of her last letter read, 'You have a son.' I never heard from her again. I've thought of her often throughout the years and of him; is he happy, what does he look like, what's his name? I'll never know and I've learned to accept that. A couple or so years later, we heard through the grapevine that Bill had died from a heart attack. I wondered if Dot was getting some black dick again but apartheid was in effect so I thought probably not.

I was back to masturbating while thinking of fucking Dot instead of actually doing it. I began dating but none of the girls could compare to Dot even though I bedded a couple. She taught me that men are generally more concerned about ejaculating in a pussy than they are of giving any consideration to the woman's needs. It was just after Christmas 1968 that my best friend, Chris, began to discuss the idea of emigrating. It was more for a change and an adventure than anything else and we settled on Canada. We landed in Waterloo, a small town in Southern Ontario and quickly made many friends. They were wild times with lots of parties and many females. More than once I woke up in the morning after a party with a young lady and not remembering how we arrived in bed together or what her name was.

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Written by TheSalaciousScribbler
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