The Rebound Guy

I was in my late40's when I was between marriages and on the dating sites trying to meet women and I found Diane. Liked her pic and so sent a message, the hit rate even back then was low but got a message back. We chatted back and forth for a while and got on well so arranged to meet for a drink.

When we met it was a relief to find her profile pics were accurate, not always the case. She had blonde hair, green eyes, early 40's and quite petite. Not the curves I would usually go for but still found her very attractive. She had separated from her husband when she found out he was having an affair with a hooker. They had been in the middle east and she had moved back to the UK, living in a house owned by her parents with her 4 kids. All of this information came out during the course of the evening as we chatted easily about things, the time passing quickly.

At the end of the evening, I walked her back to her car and wondered whether a goodnight kiss on the cheek would be appropriate. I leaned in to try and she met me with her lips which was nice then her mouth opened and we were french kissing. Very pleasant but unexpected on a first date and did get my trousers stirring. Then we broke the kiss to come up for air and said good night. I waved her off as I walked back to my car but I was thinking that I would be getting some action in the near future.

Second date I was allowed to pick her up near her house and we went for another drink, dropping her back in the same place with the same passionate kissing at the end of the evening. Bit nothing more.

Third date, I had booked a table for dinner and was allowed to pick her up from her house. Dinner was had and I took her back to her house. After I parked on her drive, she invited me in for coffee, all very cliched. We went in and proceeded to the kitchen where she made us coffee and then moved to the lounge, chatting and drinking our coffee. At some point the coffees were put down and we started kissing again, hands beginning to roam a bit. Things were getting heated now and stopped and she said

"I am not sure if we should go ...." indicating upstairs.

I pointed to the obvious bulge in my trouser front and said "I would like to."

With that she took my hand and led me upstairs quietly so as not to wake her kids. In her bedroom, she undressed very quickly, which I would have liked to do but followed her lead and did the same before jumping into bed. Her tits were smaller than expected (damn you Wonderbra!) but lovely pert nipples which I quickly latched on to. She was very keen and after a quick discussion about her not being on the pill and neither of us having any condoms, we went for it anyway. I easily entered her missionary and we quickly settled into a nice rhythm, At the point of climax I pulled out and came on her belly, both very happy with ourselves. After a clean up, I dressed and left as she did not want me to stay with her kids in the house.

That was the start of a fairly short but active relationship. She had clearly been lacking a sex life with her husband plus that sense of freedom. I will now relate a few memorable moments from those few months.

I worked from home even then and she came round one day early in the relationship, bringing me lunch. That quickly became a bedroom session and I had condoms so we were able to really enjoy things. As we lay in bed afterwards, I pointed out that I was technically being paid to fuck her since I was supposed be working.

She was definitely up for trying new things and can vividly remember her riding me reverse cowgirl. She was so petite and my cock looked huge sliding in and out of her pussy, I even commented on how I wish I could take a pic so she could see. She didn't say no but I not have my phone nearby and was having far too much fun too.

On another occasion she came to my house one evening and we quickly headed to the bedroom. After quickly undressing (a common theme),she lay on the bed with her feet on the floor as I went down on her, licking her to orgasm which I love doing. When I had finished she offered to return the favour and I wasn't about to refuse. Being a gentleman I asked her if she wanted a warning when I was going to cum and she said yes.

She was doing a very good job and when the time arrived I let her know but she stayed in place. I couldn't stop myself and came in her mouth which she then swallowed.

When she lifted her head I asked if she not hear me but she said

"Yes, I had never done that before so thought I would try it."

She was in her 40's and never take a load orally. I then asked if she liked it but she was not convinced. I sadly did not get a second chance with her oral talents and I do wonder if she has tried it again or I am the only one to have cum in her mouth. When we had finished the oral session, we got partly dressed and went downstairs to have a drink and watch some TV. Some time later we started kissing and headed back upstairs, her arse in knickers lovely to see as I followed her upstairs. She was on the pill by this stage so we were fucking bareback and after a good long, satisfying fuck she says

"Well, that was a first."

I wasn't sure what she meant and asked

"What? first orgasm?" and she replies.

"No, first multiple orgasm."

And yes I was very pleased with myself for that.

Once we had gone back to hers after an evening out but as we headed up the stairs, one of her daughters came out of her room, I quickly slipped back down to the lounge while she dealt with them. She came back in and said she was worried about going upstairs with the kids awake but we were both pretty heated so I suggested she go and put something loose and more accessible on. She disappeared upstairs and I wondered what she would choose to wear but I did not expect the big dressing gown she returned in. Happily I quickly found out she was naked underneath it and in no time I was on my back on the sofa, trousers down and she climbed on top of me. She was very horny that night and was riding me hard.

I moaned "oh, fuck" at one point and she stopped thinking she had hurt me.

I reassured her and encouraged her to go for it as it was fantastic. So to our mutual satisfaction she did, always loved the woman on top and that is a memorable instance of it for me.

I remember the last time we had sex, end of the evening out and in her bedroom and I ended up fuck her doggy style. When we had finished and I pulled out, there was blood on my cock and she said she had just finished her period. I didn't mind at all

After as was usual, I dressed and left. I never once stayed overnight at her house although she had stayed with me on a few occasions..

Shortly after that she sent me an email, saying she was confused as her ex husband had tried to kill himself and she wanted some time to sort her head out. Unfortunately, the next day she posted on Facebook that she was in a relationship with another guy! While I did not think we had a long term future, I was still pretty crushed but moved on with life. A month or so later I got a "Dear John" email saying she didn't want to see me anymore etc, which I had worked out for myself. So replied confronting her with the other guy, she said he was an old friend and they had re-connected but didn't know how to tell me.

It was only later I realised that I was her rebound guy and the other guy, who she is still with 12 years on, was the better long term option. I do still wonder if he gives her multiple orgasms or she swallows his load when giving head but guess I will never know. At best I am the only guy to cum in her mouth and at worst one of only two.

I will take that.