Swinging
31 May 2016


Chapter 6 The Dating

Dating in this new century as a middle aged, educated, financially stable and divorced male is not a breeze. While the thought of having to approach a straight woman for a date may have terrified me twenty years ago. I was once referred to as a player, but this was after many years of dating dozens of eligible single or divorced woman. All of them very different and yet very special to me, I came close to being very in love with most of them and my one claim to fame is a I remain friends with all of them. I am not in contact with many for various reasons and yet wherever we meet or come into contact there is nothing but pleasure in seeing each other. This includes my ex wife as well as the longer-term relationships I have had. Anything over 6 months would be about the standard.

Much had changed in my life, part of that was a decision to start dating again and to give up my so-called promiscuous life style. Well to an extent anyway. Being single I was in a position to date whomever and whenever I pleased. I became bored with swinging, and the sex left me unfulfilled. I masturbated often, but more about that later. I was looking for more in depth relationships, friendships and maybe even a long-term loving relationship. Where does one meet intelligent available women. Clubs, Health Bars, Singles Clubs, The Internet? I was already an Internet junkie so I turned to the softer , dating only web sites. Try and find a relationship , maybe even romance and then the sky is the limit. There is just as much sex available out there for singles as couples. There are also a lot of lonely people looking to meet Mrs/Miss Right. So I joined and placed ads through a dating website or matchmaker website. I also made myself available through friends and contacts. I was well and truly back in the game. I was working in a corporate environment again meeting new people and I was dating again.

I met some fantastic women, though friends, various chat rooms, dating sites and singles parties. I developed all kinds of new relationships, coffee friends, dating and fuck buddies. Everyone to there own. Sometimes some of these relationships were quite complicated and had potential for a long-term relationship. Many were purely sexual, two adults enjoying themselves without too much baggage. Going back into dating in your forties can be a scary experience, but it is also very rewarding and fulfilling. Having been single for a number of years I had many chances to date and meet different woman. Some of these stories became my lifeblood, my absolute passion, to be a completely passionate, caring and considerate lover. There is nothing that I would not do with a women, to achieve the ultimate orgasm. I saw a lot of those, from spraying to whimpering pleasure. My sole aim in all my relationships was to give the women in my life total pleasure, passion and the best sex of her life. Many of these women fell in love with me.

I had been divorce for about four months when I met Jan through a mutual freind

I met Jenny through an Internet dating site. Thousands of single men and women use technology to meet and find new partners. We live in a world where introductions, new friendships and contacts can be made anywhere in the world. Chat rooms, dating sites and the access to the Internet, bring the world into your living room.

We had been communicating for some months before we agreed to meet. Coffee, a chat and learn a little about each other. She was divorced, two kids, good job and career orientated. Our first date was a lunch with friends, where we both proceeded to get pissed and naked in the pool. From there it was not long before we back at her place and tearing of each other’s clothes. With her kids asleep, we made out on the couch. I was stroking and fingering her pussy, Jenny was very horny, wet and loved sex. We fucked each other for most of that night and in the weeks that followed. The pattern was repetitive, a few glasses of wine , put the kids to bed then sex on the couch. She loved me going down on her, thrusting her hips forward to get as much tongue as possible was always wet and had a loose cunt. Too many kids or too much sex? Never enough sex. The relationship lasted a few weeks and we called it quits.

I met a 38 old divorcee, Rita, we had become friends years before, but never pursued a relationship. She invited me to a premier’ black tie and after a great evening she invited me to her place. I was somewhat surprised as we had dated before and never gone any further. Arriving at her place and as we got in the back door, she was coming onto me strongly. There was no talk, she wanted sex and made it very clear. From this straight talking intelligent female, became a wild woman when the door closed.

She was so horny and forceful I was taken by surprise, I was normally the aggressor or initiator in sex. On the way home she started massaging me through my pants, by the time we were inside I was half undressed and so was she. Pushing me back onto her couch she held my cock against her wet juicy hole and started rubbing the head against her clit, all the time saying how much she loved cock and wanted to be fucked. She was really hot and did not take long before she had a huge orgasm. I had only ever experienced a woman who “gushes” once before. She was so wet and slippery and I was covered in her cum. When I entered her she was moaning and begging me to fuck her, while at the same time she kept asking me not to hurt her, telling me I was too big. Fat chance of that, she was so slippery and wet, I fucked for the next few hours. We tried most positions , but she only came when using my cock as a weapon against her clit.

I left early the next day, my cock was raw and quite painful. Her fanny hairs were hard and course, making it a very painful experience. No wonder I have come to love shaved and hairless fannies. We dated and fucked each other for the next week, she has a really beautiful pussy, never had kids and was always tight and willing. I even started to believe we may have along term relationship. Maybe I should have settled down and given it a chance, but she had never been married had and her agenda was very different to mine. I was not ready for that although the thought was attractive. Our relationship lasted a month and we agreed to date other people.

I met Kimberley through an Internet dating site, also a divorced mother of two, a very artistic, woman who owned and ran a very successful business. We had a number of coffee dates before starting to date. She loved music and we would often watch live performances. When I met her she was still in love with her ex boyfriend. He had taken a post overseas and they had split up as a result. It was after one of these coffee invites at her house that we finally made love. Well let me rather say, I made love to her. The sex was very good, she is a tall woman , big hips, and very nice firm tits and loved sex. Once again it became a regular arrangement. Coffee with her, put the kids to bed and then sex. I started visiting only later in the evenings, often on short notice.

Sometimes she would call me during the day when she had a weekend off and then she would visit me. Most of the time it was just sex. She would speak about her ex and the cyber sex and messages he was sending her and then she would fuck me. Despite this I liked her very much and while not potential for anything more, we had some great evenings together and my neighbours must have got an earful. She was extremely vocal when cuming. She also loved to give head and would always blow me before we had sex, which I appreciate as so few woman realize the importance of sucking a man’s cock, like we love to lick their cunts.

Roslin and I met at a corporate function. She was divorced, highly educated, and held a very high position in an accounting practice. She held numerous degrees, was a more than responsible parent and very introverted. We went on a number of dates together. I never believed there could be any long relationship, although we got on well. We enjoyed each other intellectually long before it became a physical relationship.

One evening after a party at her home all the guests had left, we were kissing and fooling around on the couch. I was teasing her nipples through her blouse and rubbing the palm of my hand outside her jeans I was getting quite hot and heavy when she grabbed my cock and started playing with me. Removing all her clothes I had a very pleasant surprise. She has a beautiful body, lovely round tits, a small ass and soft black pubic hair. Her cunt was framed by black hair, and as she lay back with her legs open I got an eyeful of her cute asshole and wet open lips. I licked her to multiple orgasms before entering her. Later that night, I was sleeping on her couch, when she came down stairs and joined me in the early hours of the morning we made love again. The sex was very good, nothing kinky or out of line, she loved straight cunninglus, followed by missionary sex. I never saw her again after that as with all the intellect in the world, it was not a replacement for great sex.

My life would not be complete without at least one story of meeting a woman at a pub having a party and getting laid. I met Christina at a club in Boksburg and after we exchanged phone numbers we agreed to meet again. Christina is a 33-year-old divorcee. Ex husband is a gangster and body builder and was not to be messed with. He had left her for another woman and she was really pissed off. After going out one evening we ended up on a pub-crawl, which ended up at a rave club. Buying E we partied until the early hours of the morning before heading back to my place to finish the party.

She is a petite, beautiful woman and very sexy. We had only just got home, when she started touching and feeling me up. Taking her upstairs to my bedroom, I slowly stripped her to her underwear, before lying on the bed and proceeding to give her a full body erotic massage. Whether it was the X or the whole evening, she was totally aroused. Removing her bra and panties I massaged her from head to toes, eventually sucking and licking her small beautiful feet and toes. Turning her around I repeated the performance. Spending ages sucking her nipples and stroking her breasts. Nothing was left untouched or teased. Looking down at this gorgeous woman on my bed, I lifted her bum off the bed and opened her legs to lick her from her ass to her clit. Every time I sucked her ass she would moan in delight and lift her hips off the bed. I don’t know how many times she came that night, but each time she erupted was stronger than before. I was floating on X and wanted all of her. After fucking her for over an hour, she turned over and lifting her ass in the air asked me to fuck her in the ass. Using her fanny juices and copious amounts of KY, I slowly worked my cock up her asshole, As I eventually slipped up her bum , she opened for me and I could fuck her hole, while holding her clit firmly between my fingers. As I shot my load up her bum she came again. It was a fantastic evening, but I never saw her again. My life was worth more than that. We had used each other for one night of fantastic sex. Whether she ever told her boy friend or it was a revenge fuck, she really was worth every effort. Then again maybe the gangster found out.

I have dated a string of women, divorced, single widowed and some even married the story would never be complete unless I had another affair. This time I was single and she was married, but he was unaware of his wife’s passion for sex. We had known each other for years and often flirted and the suggestion was always there. Years earlier we had kissed and touched, but never gone past some fooling around. Being the “third” person in a relationship was not knew to me, but I was now “ the other man” It lasted for 6 months, we met secretly went to obscure pubs and restaurants, or my place for sex, the sex was good , always satisfying, but not enough. She had to keep to a tight schedule. After many months we mutually stopped and years later she divorced, and we remain friends today.

There were many other dates, possible relationships and even sex. All consensual, two adults meeting, getting it on, or just fooling around. One such evening at my local pub, I met up with an old friend. We had flirted for years, even before I was divorced, but it never went any further. I am not that sure where or how we ended up in bed, but we were both very drunk and I did regret it the morning. We had known each for a long time and although we had fooled around and she had given me a blowjob one night in the car park we never actually had sex. That is until we ended up, both at the end of a relationship, getting pissed at the pub, until we eventually went to her place. She fucked me properly. I wondered why we had waited so long, we remain friends and have never repeated the performance.

There have been many memorable evenings, great dates, and fun over the years, but I could not find what I was looking for. It was not the woman in my life for I loved them all , but the problem was in me. I was never totally satisfied, with any of these relationships, something was missing. Maybe I needed to fall in love or find someone who would love me for me. I always knew Anita loved me very much and despite our break up we had kept in contact. I was very busy, working, building and travelling to the coast where I had business interests.

I had my fair share of failed relationships, I was not always the one who dumped, and I also got fucked in a few of these relationships. Women can be more manipulative and cunning than any man. They have to if they want to succeed in this world. After all I am a very eligible divorced white male. The fact that I can fuck too near perfection and I continue to strive to that level, is a bonus. Women talk , my reputation preceded me.

In the meanwhile my then ex had moved to the coast, we had seen each other briefly before she left, where we had made peace and then love. In hindsight a mistake, not at that time I was truly searching for a normal relationship. The sex was fantastic she satisfied me physically, we enjoyed many similar interests. Mentally and with my and her past it was doomed for failure. No love in the world could stand this amount of abuse and survive. We tried anyway, against the wishes of friends and family who all were shocked when they realized we had got back together.

On one particular weekend after she had moved to the coast, I met up with her and we disappeared for a few days. We had a lot of fun, and the sex was better than ever. That Christmas I had a wonderful holiday and time with this woman I thought would be my saviour. Of course my past and her jealousy and mistrust would destroy that dream. Which was clearly justified as she had learned of my past and knew my history. I would not admit the truth to her. My secret has remained hidden all these years, she was too close too the truth most of the time, but never completely. Anita always expected I was having other relationships. In some respects she was right and eventually later on I did prove her right. I was not monogamous and never had been. However un monogamous I was I always loved each of my women

Let me not take all the blame here, she was a very manipulative and clever woman. She tried to play me like a fish on the line, knowing she had hooked me, sexually but then her own insecurity, mistrust and past took over. She could not show me any trust or respect for my privacy. Reading old Christmas cards or tearing up woman’s clothes do not make for a future relationship. Can one trust the ‘devil’ in one’s house. That’s my devil so I can trust him more than you can. We eventually broke up, but Anita came back into my life at a later stage again. Or may I say, at a different time zone.

The truth is sometimes not what its made out to be. One of the main reasons I started to tell this story was because, I had hidden the truth for so long. It was in that year that I met Denise.

Denise and I were introduced at a friends wedding. We have known of each other for many years, both having married child hood sweethearts and over the years we had developed mutual friends. She is a widower with two great teenagers and a close circle of good friends. We had been jointly invited to a wedding , to which we agreed to go together and enjoy the party. Denise is late thirties, very liberated woman with a career, sons and the rock of Gibraltar. On the outside is a woman, single mother in control living in the 21st century. She is also a stunning 5’8, dark thick hair, beautiful green eyes, slim , and very sexy. When she crosses the room people notice. I had never taken real notice until that day. She oozed confidence, which I later found out was all acting. I was very impressed

The particular wedding details are hazy. However that first night with her was complete bliss. We had danced all night , then gone clubbing. Kissing took on a whole new meaning with her. The chemical and physical attraction between us was instantaneous. Watching her from across the room, I knew deep down in my heart I wanted this woman .During the course of the night the attraction became more than physical, we spoke , we had a great time. She was intelligent witty and has a great sense of humour. We laughed chatted and I flirted. Touching the small of her back while we danced or just resting a hand on her knee. She did not object. If there is one thing I want to remember about the past it is that feeling. There was no doubt I could fall in love with this woman.

The evening at the wedding and what happened live in my memory. After the wedding and close friends left we were left to enjoy each other. We both wanted a wild night something to remember. Although I had been hopeful I would have a great date this was turning out better than I could imagine. She was very sexy, with tight black pants, and I could see her perfect tits above her blouse. When she talked her voice was soft but firm. She told me a few times that night. No! each time making me try harder. We did eventually get home , both hot and tired, but very horny. On my bed I removed her clothes and looking down on her narrow waist and soft tits, her fanny neatly trimmed and full firm lips. The mouth and the tongue are a wonderful thing, we made love that night everyway possible. Her taste her smell soft skin there was no holding back she wanted me as I wanted her. Everything I have tied to learn how to please a woman was what I wanted for her.

Over the next months , our relationship and the sex grew and was enormously rewarding. I was ecstatic at having met such a woman. Maybe I was naïve. Here I had met the exact opposite to my lifestyle. How could such a relationship work, but it did. I had one last thing to do though before I could fully commit to this woman. If she would have me.