The Ladies of My Life

I was born in 1946 in the UK and grew up there. It was a much simpler time to be a kid and I look back on my childhood with much fondness. Back then the world was a vastly larger place and compared to the children of today, who literally have any and all information at their fingertips, we were terribly naive and innocent.

In 1968, at age 22, I migrated to Canada with my best friend, Chris. 

This is the saga of some of the most memorable ladies in my life that I had the good fortune to be intimate with.

I unabashedly love all of the female body! Their legs in stockings and heels, the curve of their hips, their waist with a garter belt and straps sliding over naked thighs to stocking tops, the erotic sway of their bottoms, their full breasts, hard nipples and, of course, their pussies whether haired or bared they are all the same yet all so different and the centre 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 on when you are pleasing her. I've been very lucky to have been intimate with many sexy, erotic, horny ladies with terrific bodies who love love to dress for sex and love being fucked.

I'm not sure how old I was when I awoke one morning and my cock was strangely hard. It had never happened before and when I moved my hand over it to investigate it discharged a large amount of thick, creamy liquid. I had no idea what was going on but did it ever feel good. Over the following days I entered into an intensive examination and experimentation of my new toy and semen flew in all directions with regularity. After a very short time I became an adept masturbator. 

I now graduated to frequent masturbatory fantasies of sex with mature female neighbours even though I wasn't sure what that all entailed, I guess there's a certain amount of innate behaviour that takes over. One neighbour in particular monopolized my wanking joys and she lived next door. Her name was Dorothy, "Dot" to all who knew her and I would 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, often in a short skirt and I could see up her skirt almost to her panties which, at the time, was the height of eroticism for me and I'd jerk off and cum all over the window.

She often visited my mom for a chat and a cup of tea and if I was home would leer at her every chance I got. I wondered what her large breasts looked like under her clothes and if her pussy was wet and hairy. I'd get hard thinking of these things and I was convinced she had seen the bulge in my pants on more than one occasion. I had just turned 18 and as she was leaving from a visit with my Mom she looked at me and moved her eyes in a way that indicated she wanted me to follow. I did after a minute or two and saw she was standing by her open front door. We didn't speak, I just followed her into the house.

Dot wasn't slim by any stretch of the imagination, she was a well-built woman with large breasts and a lovely large ass but her body was perfectly proportioned and I lusted after her so much. Neither was she pretty in the conventional sense but had an unmistakable raunchy, sensual and sexual appearance. In the living room she sat on the sofa and told me she had seen me looking at her and knew she excited me. 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. She 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 seemed ready to burst out of her bra. The 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.' Dot unzipped my jeans and pulled them down.

She gave my cock a couple of tugs and I ejaculated all over her tits. I had three overwhelming emotions as I stared at her massive breasts, now splattered with several long, 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.

My unabashed lust for her was the only thing that stopped me from running out of the house. 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.' She then rubbed my cum all over her tits and put her fingers in her mouth, 'Umm, you taste good and I want to taste you a lot.'

'Pick up your clothes and follow me,' Dot said and I watched her great ass climb the stairs. She pointed to a bedroom, 'Go in there and take your clothes off, I'm going to clean all your lovely cum off my tits.' I got naked while she was in the bathroom and stared at her gorgeous breasts when she returned. She unzipped her mini-skirt and wriggled out of it then knelt on the edge of the bed and lowered her head onto the sheets, forcing her ass higher in the air. 'Pull down my panties,' she said and I obeyed with trembling hands. I stared trancelike at the first woman's anus and pussy I had ever seen in the flesh. Dot then spread her legs,  stretching her panties as far as they would go fully exposing her pussy.

I gazed at the spectacular wet pink gash surrounded by a dark, hairy fringe and if that wasn't the most erotic sight I had ever seen, she opened the gash further with her fingers, 'See how wet my pussy is, you've done that with your big load of cum splashing all over my tits.' I could feel my cock begin to twitch when she said, 'Kneel down, I want you to feel me, kiss me and lick me.' I would have licked her entire body if she had asked me to and I knelt down and fumbled rather than fondled her butt cheeks and pussy. It was the first of many wonderful sexual firsts I experienced with Dot. My cock was now fully erect and she rolled onto her back and removed her panties. She lifted her legs and spread them open and I looked on in awe at her gaping cunt and anus, I had never seen anything so erotic and to this day I love to gaze at a woman with her legs spread wide displaying that wondrous, creamy hole in the most lewd and obscene ways. It's an old but true adage that men spend nine months coming out of a pussy and the rest of their lives trying to get back in.

'Come and lie with me, there's lots of time to fuck me before you'll have go.' Those words, 'Fuck me,' coming from Dot were the most erotic words I ever heard. I lay next to her and we embraced, her tits pressed against my chest and she kissed me on the lips and her tongue wrapped around mine. I felt dizzy with excitement, there were so many incredible things happening so fast. Her hand caressed my cock and balls and I squeezed the soft mounds of flesh on her bottom. 'I want you to fuck me, let me put your cock in my pussy.'

I rolled between her legs and was unsure exactly how to proceed but she knew and unceremoniously guided me into her mature, well-used pussy. I say "well-used" because Dot had a definite slutty look and I imagined a lot of cocks had enjoyed her. I only lasted a minute but my ejaculation was nirvana and I lay on top of her until my cock softened and slipped out. Regardless of our short copulation she was savoring the moment and hugging me tightly and whimpering quietly. Later, I mauled and kissed her huge tits, fingered her pussy then she instructed me how to eat it. I had never tasted so much of my own cum before but it wasn't unpleasant mixed with her cunt juice as it was. 

It was difficult for Dot and me to get together for several reasons; she had three kids, I worked and it was next door to my home so we needed to be careful but we got together every chance we had and fucked like rabbits when we did. I learned fast and was fucking her brains out and almost always cum twice. She was a great cocksucker and I loved to jerk my load into her open mouth and over her face. Fucking her from behind was a dream, I loved looking down at her ass and my cock sliding in and out of her cunt and I often sprayed my semen all over her ass then licked it all up. After six months I had learned well and took control of our sex life, Dot liked being submissive and I now knew enough that I could take the lead. She told me that Bill, her husband, wasn't 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 innocence of youth.

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. 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 that we could. 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 would go in by herself and get the room then come outside and tell me the number. She insisted I wait 45 minutes before coming up to the room and it was the longest 45 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 breasts were spilling out in a most erotic way. Her black mini-skirt was so short I could see her stocking tops and garter straps and her heels made her taller than me. 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 passionately 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 love 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 woman. It was the first time I had slept with a woman, although there was not a lot of sleep! 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 while she kept my soapy cock fully aroused. We left separately in the morning after having sex and continued to get together whenever we could. 

In August 1966 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 would follow in two months. The sex was terrific and very frequent during those final days, 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 2 or 3 times a week. Her eldest son had a part-time job where he worked until midnight so every time he was on shift I went over after she put the other two children to bed. We meet in a nearby woodlot on a golf course at night and Dot would bend over a fallen tree trunk and I'd give it to her from behind. I also took a few days off work and we'd fuck all day while the kids were at school.

I felt a great loss after Dot was 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. 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 that were enclosed with letters from her son, Barry. She was pregnant and certain it was mine but things were much better between Bill and herself and they were having sex again 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 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 is his name? I'll never know and I've learned to accept that.

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 1967 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. 

Two years later I took a job in London, Ontario and it was to be 2 years of very active and varied relationships with single, married, separated and divorced women that came my way with virtually no effort on my part. I checked into the YMCA until I got my bearings and decided if the job suited me. Around the corner from the Y there was a small restaurant and I went there each night after work for dinner. I went back to Waterloo most weekends but each weeknight, except Friday, I could be found in the restaurant. I'd been going for a couple of weeks and one evening I gave the waitress my order. She had served me most of the times I had been in and we had a brief chat. When she left the table a head popped out from the next booth and the young lady said, 'That's a neat accent, where are you from?' I thanked her, told her where I was born, we smiled and she withdrew back into her booth.

After my meal the head popped out again and asked if they could join me. I knew there were two of them because I passed their booth on the way in. I said sure and they sat opposite me and introduced themselves as Yvonne and Elaine. We chatted over coffee and went our separate ways. The following evening Yvonne was sitting in the same booth and smiled and asked if I'd join her. That was the beginning of our relationship and about a week later I moved into her apartment. It was a studio and quite small and as her lease was nearing an end we decided to look for something bigger.

We settled on a house that had been converted into three living spaces. The top floor was occupied by a single mom and her young son, we had the main floor and a young couple lived in the basement apartment. We got along fine, there were no problems and life was good. Yvonne and I became friendly with Brad and Jessica who lived in the basement and would visit one another on Friday or Saturday night. We liked the same music, drank a few beers and occasionally smoked a little weed. One evening Brad and Jessica began to kiss and fondle on the sofa. Yvonne and I followed suit on the floor and it progressed to us fucking. It was very erotic and I could see that Brad and Jessica were as interested in watching Yvonne and me fuck as we were of watching them. 

The following week Brad and Jessica came upstairs to our place and we began as usual, having a beer and listening to my most recent LP purchase, "Aqualung" by Jethro Tull. Brad and Jessica started to get it on and Yvonne and I followed. The four of us were on the sofa with the girls were sitting astride us. Brad reached over and fondled Yvonne's tits and I responded by fondling Jessica's. There was no resistance and when Brad suggested they change places they did so without comment. I discovered watching Yvonne being fucked by another man immensely erotic and it's a fetish that has continued all my life. After that night we swapped partners every time we got together and enjoyed many very erotic foursomes.

The relationship between Yvonne and me was running its course. At the very beginning I had said I was not interested in a serious relationship but I sensed Yvonne was a lot more serious than I was and we went our separate ways as far as living together was concerned but we still got together for sex, usually on weekends. Yvonne shared a house with a couple of friends and I moved into a new apartment building. I had 3 or 4 young ladies that I would see from time to time and tended to stay in London most weekends now. Females drifted in and out of my life with ease and most ended up in my bed. I had been seeing one woman who was divorced and in the court system regarding custody of her kids who were living with her ex husband. She never offered any details and I never asked.

She was friends with a married couple and they were moving house and asked if we would help. It was a long and dirty day and when we had finished the husband ordered pizza to go with the beer. Shortly after we ate pizza, friends of the couple visited which I thought strange since they had just moved house but different strokes and all that.

We sat and chatted and I realized that the woman was paying a lot of attention to me. Her husband worked at the local TV station and it seemed to me that she wore the pants in their marriage. She was plump but in a very pleasing and sexy way. Her clothes and make-up were elegant and I figured she was high maintenance and her husband worked lots of hours to maintain her. When they were leaving she cleverly slipped a small scrap of paper into my hand and gave me "the look!" It was a phone number and the words, 'Call me.'