This is the first part of a series where each part can be read with or without having read the previous parts.
Prior to the age of 48, I’d only had sex with two women. Then I split from my wife and had two fantastic years of sex with a lot of different women. Now, years later, I’m married again and still have the memories of the wonderful women with whom I had so much pleasure. These are the true stories of the wonderful women of my life. I love these memories and want to share them.
But first, in this chapter, I describe my early sex life and how I came to be 48 and only had sex with two women.
MY FIRST TWO SEXUAL PARTNERS.
I was definitely a late starter. Throughout my teens and into my early twenties, I never had any sexual activity, nor even a semi-serious relationship, with any woman. It was not for lack of trying, but I didn’t seem to be attractive to women. I was socially awkward around girls, and the more attractive they seemed to me, the worse I behaved. I had been to an all-boys high school, so I don’t think that helped my education concerning women. By the time I was 20, I was in my fourth year at University and had met dozens of girls in classes and in the on-campus groups I’d joined. But they were all either attached to someone else or I just couldn’t get started on asking them for a date. I would hang out with my mates and meet attractive women but could never even get to a basic “liking” relationship with them, much less go on actual dates.
One of my mates got engaged and at the engagement party, I met a friend of his fiancée, one of the girls in the bridal party. She and I had a few interests in common, and while talking with her, I realized she was unattached and about as socially awkward as I was. So I asked her out for a date, and we actually had a nice time on a couple of dates, but soon enough we both realized this was futile and it just evaporated. This kind of failure with girls was what I’d come to expect.
When I was 20, I moved out of my mum’s house and went to live in a house with 3 other friends who were also at University. This turned out to be quite a major change for me, releasing me from my mother’s influence for the first time.
JENNY.
I had just turned 21 and was still a virgin when one of my housemates brought me along to a party thrown by one of his friends, and that’s where I met Jenny. She was beautiful: perfect olive skin, blue-green eyes with brown flecks in her irises and long, straight light brown hair. I acted pretty nonchalant, expecting her to turn and walk away any moment, but she kept talking with me. My housemate went home, and with him went my transport. By about 2 am, her friends had left, and she had no transport. So I walked her to her place, about 3 miles through the city, through parks in the cool night air while not a soul was out except us. After a while, we held hands as we walked, and when we got to her place, we kissed good night; a little kiss at first which quickly became a deep tongue kiss like I had never had before. As I walked back to my place, another 3 miles, I was on cloud nine.
The following Friday we had our first date, dinner at a Mediterranean restaurant near my place. All through the dinner, we were checking each other out, but being polite and discreet. I was excited, although not knowing what would happen or how. But here I was, on a true date, just me and this beautiful brunette. I was in completely unfamiliar territory and loving it.
When we finished at the restaurant, we went back to her place, we headed straight for her bedroom, locked her bedroom door and, standing in the middle of the room, started kissing passionately.
After a minute, we broke for a breath and she pulled her sweater over her head. Following her lead, I unbuttoned my shirt and stood there naked from the waist up. She undid my belt buckle and jeans and they dropped to the floor, leaving me standing there with a huge erection in my briefs. I bent down and took off my shoes and socks, stepped out of my jeans and then helped her lift her dress over her head, revealing a beautiful curvy body with broad hips and plump breasts, as she stood in her white bra, panties and tights. She pulled the top of the tights down below her hips, then sat on the edge of the bed and I carefully rolled her tights down her smooth legs. As I was finishing taking her tights off, she reached around and unclipped her bra, releasing her firm, plump breasts with their erect, pert little nipples. I dropped my briefs to the floor as she wriggled out of her panties, revealing a full bush of curly brown hair. I lay down beside her on the bed as we kissed some more and pulled each other close to ourselves, enjoying the wonderful feeling of skin on skin.
She had my cock in her hand and was gently massaging it, spreading around my pre-come and rolling my foreskin back and forth. I later learned that mine was the first uncircumcised cock that she had had, and she was enjoying exploring and observing how the head could be hidden and then pop out as she pulled the skin back. I had not much idea what I was doing, but I was gently fingering the outside areas of her cunt and spreading her juices around her lips. We were both super excited, so the foreplay was short, but my cock was as hard as steel and leaking pre-come copiously.
In retrospect, it was fortunate that she was as turned on as I was, because she was nice and wet even with the minimal incompetent foreplay that I performed. She rolled on to her back and lifted her knees in the air, showing me her perfect pussy. This was the first time I’d seen a woman’s pussy live in the flesh and I was awestruck. She motioned for me to climb on top, and then she took my hard, slippery cock and gently guided me inside her. This was one of the most incredible events of my life and even after all these years, I still recall vividly the feeling as I entered her. During the previous five minutes, my cock head was so hard it felt like it would burst, and she was gently stroking it.
As it was out in the open and covered in my juice, it was slightly cool. But upon entering her, I was overcome with the sensations coming from my cock. It felt so warm, the perfect temperature, especially after being out in the open; her cunt gripped my cock with a perfectly even pressure all over, unlike my hand when I masturbated; and there was no friction, just smooth sliding into her warm wetness. The physical sensations were enhanced by the emotional sensation of being united with this gorgeous woman, part of my body inside her body. I was so excited and inexperienced that as soon as I entered her, I started coming immediately. I did not have time to start thrusting, I just slid slowly inside her warm, tight, wet cunt and my cock immediately started squirting. I said “I’m coming” because unloading my sperm inside this beautiful woman was a huge event for me, and she just smiled. The feeling was so amazing that I then started pumping, but this only went for a short time, as my cock, having delivered its load, went soft. We lay in bed, naked and enjoying each other’s bodies, for about half an hour, then I had to leave, because she did not want her housemates to discover she was fucking me.
For three lovely months, we had sex frequently. We did it in her bedroom, especially when her housemates weren’t home. Her dad was overseas, so his flat was empty, so that was handy. At his place, we did it in the shower, standing up; we did it on the living room floor; we did it on her dad’s leather sofa. I was completely inexperienced and she was fairly conservative in her sexual desires, so our sessions were always conventional straight fucking, although we did use a variety of positions. One of the best was on the sofa, with me sitting and her straddling me, facing me. This was a great position because my cock could get really nice and deep into her cunt and at the same time, her tits were in my face and I could kiss and lick them as we fucked.
I quickly learned that having regular sex was everything it was cracked up to be, and I really felt in love, thinking about her constantly and wanting to be together. The problem was that she was Jewish but I was not; I wasn’t even circumcised! So that relationship did not have a future, and after three months she left to go on a vacation in Europe, so that’s when we split. I thought about her all the time, but my life returned to normal: study, work on weekends to support myself and no girls to distract me from either of these activities: back to my normal celibate lifestyle. It’s said that you never forget your first love and over forty years later, I can attest to that. I sometimes wonder where she is and how her life turned out.
MONICA.
A year later, I met Monica at a friend’s dinner party. She was a vision, utterly gorgeous: tall, curvy, with long red-brown hair, and long legs which led to the tightest, roundest most beautiful backside I had ever seen in a pair of jeans. My friend had constantly spoken of her and her backside, and he wasn’t wrong. She and my friend were at a College together and he had been trying to get into her pants for a couple of years without success. Of the six people at the dinner party, she and I got the drunkest and had a ton of fun being silly although there was nothing sexual going on at that stage. When the party finished, I got a lift home with her and her friend, who was the designated driver and remained sober. In the car I got to know her better and was quite besotted with her, but in my inebriated state and with my normal awkward behavior towards women, I forgot to get her number.
But I couldn’t get her out of my head, so I called up my mate who had held the party, thanked him for the wonderful evening and asked him for her number. Armed with some sort of bravado or confidence, I asked her on a date to a local Chinese restaurant the next weekend. This was mildly comical as the tables were so small, and we are each tall, so our legs kept rubbing against each other under the table as we kept apologizing to each other for bumping. That physical contact got us both turned on, so that was a good thing.
Afterwards, we finished up at my place, and at her instigation, retired to my bedroom and got naked in bed on the first date. I guess she wanted to just check me out and show me herself, because she wouldn’t let me inside her so soon. She was stunning: tall, long legs, athletic build with perfect tits that filled my hands, the sexiest backside I’d ever seen, and an untamed bush of curly brown pubic hair through which her cunt lips peeked. She said she was not on the pill, but she would start, and that we would be able to fuck in one month. We then started dating and hanging out with each other. She was still living at home, so she enjoyed coming over to our place to get away from her parents.
A month later we started fucking like rabbits and what a sexual appetite she had! She was a couple of years older than me and had been with several guys in the previous five years. She had had guys who were pretty experienced, and she was pretty assertive herself. She knew what she wanted and she instructed me on how to satisfy her. She taught me where her clit was, and how to touch her there, just adjacent to it, but to be very gentle when touching it because it was so sensitive. She told me what felt good to her and how and where to kiss, lick and nibble her. I was a keen student, and when it came to eating her pussy, I needed no encouragement. I especially liked it if she was a little sweaty and her pussy smelled like sex and tasted salty. I loved getting among her hairy bush of curly brown hair down there, licking and kissing her lips. When we first started fucking, she guided me so that my cock reached her in the right positions inside. She was a great teacher and I carried her lessons with me in future.
After I got used to doing what she liked, we got into a fantastic routine. I would get her warmed up by kissing her neck, nibbling her ears and then gradually working down, sucking her tits, each one in turn, and then kissing down her smooth belly until I reached her pussy lips. She has big inner lips, so I loved to suck those into my cheeks and push my tongue in between them, one lip on each side, and lick my tongue up and down her slit, across her clit and darting into her hole. She would be on her back, because that’s the most relaxing position for her, and I am lying between her legs, mouth on her pussy and my two arms under her legs and reaching up and around to fondle her tits and play with her nipples.
I kept on licking her cunt until she came. Then, as she writhed with the waves of orgasm rippling through her body, she would hold my head in place until she was ready to release me. I moved up to lay beside her as she caught her breath and I gently stroked her arms, stomach, inner thighs and tits, then as she relaxed, she raised her knees and I climbed above her and pushed my hard cock into her dripping wet pussy. I started thrusting in and out with long, slow strokes, feeling the walls of her cunt gripping my cock, pushing myself as far inside her as I could go. When I pushed my cock all the way in, it went extra hard and pulled the foreskin back, far inside her, and made my cock swell up. That’s the part that felt the best to me.
She shrieked a bit when I really thrusted and hit her cervix, but she seemed to get excited by that and tilted her hips up so that I could get the full length of my shaft all the way inside her. I really liked the feeling of hitting the end of her cunt with the head of my cock, and it made me pump harder. The feeling in my cock’s head was awesome. At various times when I felt my pressure building up, I would stop thrusting and just rest inside her until the pressure went down. In this way, I could keep going for longer, and she liked that too, because it gradually got her more and more excited.
As I continued thrusting in and out, going a little faster, she started orgasming again, wave after wave of contractions rolling down her cunt’s walls. Of all the women I fucked in subsequent years, none ever came as hard, as long or as loud as Monica. The waves of orgasm rolled down inside her, squeezing my cock so hard that it almost hurt. But I was so rock-hard that her contractions could never force me out; I just got more excited and pumped harder. She was writhing with her hips, and as she pushed up, I thrust as much of my cock inside her as possible. She was moaning and breathing heavily, her tits rolling from side to side and her face going red, and her cunt squeezing my cock until I could not hold it back and shot my load way up inside her.
Many times, her orgasms were so strong and long that they squeezed her bladder and she started squirting a strong stream of pee while I was stroking her inside. This was incredibly exciting to me because she lost control and the more I stroked my cock in and out of her cunt, the more she orgasmed. Then my own orgasm became a huge explosion in my head and cock. Wave after wave of orgasm, sperm shooting out of me and up into her, and she would be still squeezing, so it came oozing back out of her, all over her pussy, her hairy bush, my cock and our groins. I collapsed exhausted on top of her, and we stay there for a long while, collecting our breath, as my cock went soft but stayed inside her still, come and juice all over the place. Sometimes we rolled sideways and fell asleep for a bit, then we got up, got cleaned up and cleaned up the bed. After a couple of these sessions, we had gone out and bought a plastic mattress protector, so that stopped the sex juices from getting into the mattress. We took the sheets off, put on a new set and then get in for the night.
After a couple of months, Monica and I got a flat together and, without housemates or other people around, we could walk around naked, cuddle each other and fuck whenever we liked. We didn’t always have these epic sessions; often in the mornings before work, or in the night before going to sleep, we would just have a nice quick and easy fuck to start or end the day. Neither of us had any trouble producing our own juices, so we could get into it pretty readily.
Often, we did it doggy style, which was nice because I could view her perfect backside and also reach around and play with her clit while my shaft was thrusting in and out of her cunt. Then, just before I started to come, I could feel my cock grow hard and bigger, and she could feel it too, so she would push back against me and I would grab her round hips and thrust myself way up inside her as I pumped my come deep inside her amazing pussy.
Mostly, we did it missionary style. She liked being on her back because she could really relax into her orgasm, and I liked it because I could raise myself up on my arms and look down, watching my cock plunge in and out of her lovely pussy, and also looking at her gorgeous tits and face as she squirmed with pleasure.
I used to love fucking while she was having her period, and although initially she was a little reluctant, after a while she really got into it as well. She had a sexy, earthy smell at these times, and her pussy was of course very slippery with the blood and other juices. I loved watching my hard cock slide in and out of her, all covered in blood, and the feeling was superb. Then I pumped my juices into her, and what a gorgeous mess that was.
One day, after we’d been together about a year, we were lying around after a heavy session, my soft cock resting inside of her, when she said “let’s get married”. So that’s how I married just the second girl I ever had sex with. Over the next 24 years, we had kids, bought a house, travelled around and did all the usual married things.
Over the years, I often wondered what it would have been like if I, like my friends, had waited for a few more years to get hitched, and had more sex with more women, but on the whole, I couldn’t complain, as Monica and I had awesome sex frequently for about 20 years. She taught me a lot about how to please a woman, where her sensitive parts are and how to touch her. I learned that I found sex far more enjoyable if I could please my partner, because often it’s difficult for women to orgasm, but for me it’s really easy.
Eventually, our marriage turned into a lot of arguments and after 24 years we split up, which is how I came to be 48 years old and only ever fucked with two women.
At age 48, I was now single again and feeling like it’s time to catch up on all the sex I didn’t get when I was young. This period of my life will be the subject of future chapters.