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Pleasuring My Ex-best-friend's Wife

Posted by: Author: Age: 52 Posted on: 0 comments
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The near simultaneous breakup of two marriages resulted in unexpected mutual masturbation pleasures for two.


I have masturbated for years, first alone in my teens whilst single, then with my first wife, then masturbation-only with a mistress (this story another time!), but never with my second wife.

I had an incredible experience a few weeks ago with my ex-best-friend's wife. I must explain that David and I had met in high-school, gone thru college together, then met our first wives within weeks of each other. After 30 years he ran off with a young thing his daughter's age, causing much uproar in his extended family and among our dozens of mutual friends. His move upset me and our friendship, and coincidentally within 6 months I left my second wife (she was screwing an old boyfriend from school days).

David and his wife Anne and my first wife as well as my second wife had spent in total over a quarter century of time together, cycling, camping, going to movies, having meals together, sharing all sorts of activities. My own preference is for large-breasted women, heavy-170-200 pounds is nice-and close to my own height. David's wife, Anne, is petite, a foot shorter than I am, about 100 pounds, with tiny breasts. Not only was she not physically attractive to me, but the fact she was my mate's woman put her out-of-bounds as well. However, she was easy to talk with, cheerful, and cute.

My second wife and I separated in late winter and I was quite lonely having lost not only the company of my second wife but my best male friend too, not to mention his wife. Spring thaw brought water problems in old basements and out of the blue Anne called to ask for help at her home. Their daughter was away for the weekend and Anne had no idea of how to cope alone with the water that had come pouring in. I went right over, I mean, what are friends for? I spent three hours and helped her clean up the water using the wet vacuum from my woodworking shop. Afterwards we drank steaming hot mugs of coffee at her kitchen table and talked awhile about her acrimonious divorce and what was happening. We started making plans to go out for dinner together that night.

I rose to go home, to shower and dress for dinner, when tears began rolling down her cheeks. She reached out and hugged me, thanking me again for helping her out. It had been over two months since I'd touched a woman and I was instantly erect. I was not in the habit of touching my friend's wife in any way in 30 years. We just weren't touchy-feely with each other. I moved to break the embrace, to keep the large lump in the front of my pants from touching her, but she didn't allow me.

She looked up at me, smiled, and said, 'It's been a while, hasn't it, love?'

I said, 'Yes, it has, and I'm sorry.' I was embarrassed now and tried to open the door to leave. But she said it was okay, put her arms around me, and hugged me tightly. I was pressing into her waist. For what seemed like minutes we stood there, so close. It felt so good, my cock throbbing with my heartbeats. I probably could have cum just from the closeness. At the same instant we both tried to say that it felt so good to hug someone again. We laughed at the coincidence.

Her next move surprised me all to hell. She took her hand and pressed her palm against my cock through my pants.

Then she said, 'I can't DO you, but I want to do something nice for you.' Then she hesitated, 'Keep this just between us, ok?'

I nodded yes. She took my hand, locked the front door, and led me down the hall and into her spare bedroom. She hugged me again. I bent down to kiss her.

She averted her head and said, 'No, this is for fun, not love.' I was speechless.

She undid my pants, pulling them and my underwear down all at once. My cock sprang free, and she gave it a squeeze. Her eyes went wide like saucers and she exclaimed 'You're BIG! David isn't that big! '

I told her I had never seen David's cock, that in over 30 years we'd never been naked together. Now Anne was getting undressed, pulling her sweatshirt over her head, undoing her bra. I hadn't seen breasts that small since playing doctor with Charlotte when we were 10.

She continued, 'Well, you're HUGE! He has a little dick, not that it matters now!' She slipped off her jeans, and then moved to hug me in just her pink cotton underpants. It struck me how very tiny she was. 'I think you're going to be too big for me!' she said.

I hugged her, and she hugged me back with one arm while she placed her other hand firmly around my cock and started to stroke it. She closed her eyes and gasped. I led her to the bed. As I glanced at her, I thought she was like a 10-year-old girl-everything was tiny.

She pulled the covers back, right off the end of the bed, and lay down on her side. I lay down beside her. We hugged for a few moments while she stroked me. Then she stopped, opened the bedside table drawer, and pulled out a small bottle of lubricant. She had me break the seal, and then she took the bottle and squeezed out several drops onto the head of my cock. It felt cool as it hit my skin. I'd never used lubricant before, so it was a new sensation. She lay to my right and put her left arm around my back and reached for my cock with her right hand.

She slowly started stroking me up and down and leaned over and whispered in my ear, 'Just relax and let me do you.'

It was incredible. She was painfully slow to start, and she gradually sped up. The lube let her hand just glide up and down with no effort. Someone, somewhere along the line, showed this girl how to give a really great hand-job. She knew exactly what she was doing, everywhere she squeezed, the amount of pressure she used, it was all perfect.

Every so often she'd ask me if it felt good. I was just lying there with my head tilted back. It was amazing. Finally my orgasm started to build in me and her hand was just flying up and down. I looked over at her and her cute face was right there next to my shoulder and she smiled at me and that was it. A moment later I felt like a catapult being drawn back as far as it would go, and several seconds passed as I waited for the inevitable explosion. Then suddenly, as I gazed at her tiny breasts, I felt a great convulsive throb as a torrent of thick, sticky white fluid shot out of my penis, made an arc in the air and fell on to her upper legs.

I immediately moved toward her, grasped her tightly in my arms, her breasts pressed against my chest, and my cock squeezed between my naked body and hers, as the second convulsive spurt shot out. It was just paradise, to be spurting several more wads of sperm while actually clasping a near-naked woman to my naked body. She continued her grip around my cock until she could sense the waves of pleasure had subsided and then kissed my neck.

I looked at her and told her I didn't know what to say. She told me it was OK and that I didn't have to say anything. After a minute or two she got up and brought back a wet washcloth she used to wipe the lubricant off me. We lay there for a while, silent at first, and then she began to talk.

She explained that David had been a perfunctory lover, you know, a couple of minutes of fingering, then missionary position, in-out, spurt, go to sleep. In the end he had complained about her lack of interest in experimenting but she said that he had often left her with the 'is-that-all?' feeling. She talked on. A few weeks before, she had had sex with our friend Ronald-as she said it-accidentally. After a movie they had been doing some heavy petting while naked from the waist down. He was very tall, a very large man, and she expected a penis to match but he was actually quite small. She was straddling him as he sat on the front seat of his pickup truck. He had been fingering her and suddenly his fingers were replaced by his penis and she didn't realize this until he grunted and came inside her. He apologized, she was angry because he had been to several countries in the past year and had had sex with women he met whilst there. She was annoyed that he hadn't used a condom on any of these occasions. She also felt he talked too much among their friends.

All this talk had gotten her hotter. She said, 'I want you deep inside of me. Do you have a condom?'

I answered her quietly, 'Yes, I do, but this isn't about fucking you on the first date. This is about pleasuring you, while we get to know each others' bodies better.' It was cooler now; I pulled the covers up over us and rolled her to face away from me. I snuggled up to her back in the bed and moved my hand to her bust and started to caress her. I felt her bottom press back to meet me. I began to tease her nipples until they were standing up. I then squeezed them and rolled them between my fingers until she started to gasp. I gently moved my right hand to trace her bottom, eventually sliding my forefinger into her groin. She was beginning to squirm, to moan.

My hands slipped down to her hips and I slowly began to slip her underpants down. She gasped as they slipped off. She pressed her bottom against my erect penis. My hand went to her bush, and I could feel her heat, her moisture. I let my finger slide along the length of her cunt, now feeling so wet, and teased her by inserting just the tip of one finger between her outer lips, slowly moving it along forward until I reached her clitoris. Then I slipped my thumb up into her vagina. By now she was breathing heavily and squirming with pleasure and I started to rub there and also to alternately pinch her nipples.

Eventually, she rolled onto her back and invited me to straddle her so that I would not penetrate too deep. I opened my 'large' green TROJAN condom, rolling it on easily with one hand, as they are pre-lubricated. I knelt over her with one knee on the outside of each of hers. She took my throbbing member in her hand and placed the tip of my cock against her clitoris. She began to use it as a dildo, masturbating herself with it whilst I held my upper body weight on my hands.

After a few minutes her legs straightened, she gripped me tighter, her back arched, and a loud gasp signaled her orgasm. She continued to stroke me, and I moved off to her right side. I removed her hand, slipped off the condom, put five drops of lube inside it, and slipped it back on. I placed her hand on my shielded cock and began to stroke until she picked up the rhythm. I told her that lube inside the condom made it feel just like an eager pussy and as the last word escaped my lips I exploded my cum into the sheath.

She continued stroking me until I stilled her hand. Before I left to get ready to go out later with her, we both agreed again that the whole thing would remain our secret. In particular, her daughter must not find out. We don't know if anything will happen in the future. But I don't feel guilty about messing around with my ex-friend's wife.



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