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By (user no longer on site) OP 51 weeks ago
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I lost my virginity when I was 19. I came across Jane online through a message group, Usenet, for anyone who remembers that. She was direct and filthy in her messaging but smart not crude. A connection was quickly established, and we began to email directly rather than chat on the group. Tens of messages a day, at all hours.
Now Jane was a lab assistant in Cambridge. Maltese by origin. Divorcing. A bit, well much older than me. 53 to be precise. 34 year age gap. that would be like me and an 86 year old now, or me and an 18 year old. Anyway, age is just a number if you connect mentally. I definitely think that now!
She described herself as a 5'9" blonde rocket. She sent me pictures of her younger years, a swimming champion, you can imagine how fit she was. And she looked hot, exactly like the kind of teenage girl I thought would never be interested in me. Her messages were so amusing. She had intellect and that was very sexy. She'd say that when she drank whisky, she'd become frisky, and if it was brandy, she'd get randy. l couldn't wait to open a bottle.
One day, she was sending me email and she said that we should talk on the phone. So I gave her my phone and she called. A gravelly voice. I was confused. Is this really a woman? It sounded like it was, but I now had a doubt. I will never know why. She discussed how I was teasing her, playing with her, keeping her at arms length. I disagreed, but of course yes I was in complete control in the email exchange and knew it. She said she felt sad and I needed to give a little.
So I suggested that we meet that evening for a drink to show her that I was very real. She said to meet under the clock at The Maypole. It's a pub in Cambridge. She'll be wearing a red carnation. That's how they do it in the movies, so why not, what's the worst that can happen.
We met at 7pm. There she was standing. It was a very hot night in June. She was wearing a light blue t-shirt and shorts set, long blonde curly hair, spectacles hanging on a chain (the look doesn't sound great, think 90's style Specsavers). Her figure was hidden but partly on display, everything shapely and in the right place, like she was still 25. Definitely a MILF, although I don't know for sure if that word was used back then. A very attractive older woman. Me wearing jeans and black t-shirt, no effort put in. If it wasn't 28C, I would have felt badly underdressed. As it was, I was glad that I wasn't wearing shorts because that makes it difficult to hide the third leg which was solid as a rock as I walked up to her.
We hit it off in an instant as the banter continued. She wanted whisky so I winked and she smiled. I had lager, I'm not to change.
We chatted through the evening opposite each other at a small square table for two. Tbh, it looked like a mother and son reunion, but it so wasn't. Our feet were meeting all night. She'd slipped off her shoes and her feet were at times massaging my calves and shins. Try it, you must. It was erotic and as a result, my boxer shorts were full of swollen goods for most of the evening. One, two, three drinks later, we were holding hands, fingers interlocked, across the table. I was fingerfucking her hands, I knew what she was thinking. I took a next step or finger forward.
I leaned myself forward and moved both my palms up her foreams, inside her t-shirt, touching her skin gently, and moving upwards to her armpit. She did the same and rested her hands on my upper arms. We paused and smiled. The touch of her skin had been almost electric.
She looked straight at me, smiling, and I extended my fingers round and down onto her hanging bra-less breasts to touch her nipples. They were erect and I fingered her nipples and the skin around them. She continued to smile. She pinched and squeezed mine, and just gazed at me, so I clamped her nipples between my thumbs and fingers too. By now, any local catching a quick drink knew that we were not mother and son. Two or three minutes of pure silence as the nippleplay continued. I asked her if she wanted a final drink but she said she'd rather go because she was now extremely wet.
We walked down arms around the waist and towards the bus station. D*unk from eroticism rather than alcohol. Perhaps both. But here was the bad news, Jane. I need to be home first thing in the morning so I'm going back to my place tonight. She looked at me, not reacting. That's fine, I need sleep, she said
As we approached the taxi rank, we moved towards a wall, I pushed her backwards and we started to kiss. In fact, I got carried away and pushed her back so much that she had wrapped her legs around me and I was thrusting towards her, about to fuck her against the side of a wall by the taxi rank. She moved her lips and calmed me down with a couple of words in my ear. She was amused and chuckling girlishly. I stuffed my cock back in, as it was popping straight up out of my jeans by that point.
She said she needed to catch a cab back. So we parted with a final long and lingering kiss and gaze as her cab sped away.
I walked home completely wound up. The next day, I hired a car and moved room, I wasn't making it up, I did have something to do!
Our email relationship grew in frequency and candour over the following weeks. A lot dirtier and sex became the main topic of our verbal intercourse.
A few months later on a Saturday, we were emailing again at 11am, and she said that I should come and stay overnight, she'd make some dinner, and I could even watch Match of the Day. The subtext was clear.
She offered me a separate room. I thought this sounds fine. I asked one thing. Your husband didn't live there? She said no, he's now gone, it's just me and my pussy. Cat, I presume. Yes, she replied.
She gave me her address and I looked it up on the AtoZ. Stapleford. A residential area just on my map, quite posh. A bit remote but heyho, a weekend adventure, or rather a guaranteed fuck with a real fit woman that wants me. Something I hadn't had before. So I obviously agreed to visit. Who wouldn't!
I went back home to collect some things, a condom or three, and headed off on the bus journey, and then a short walk. Not a big trek, so by 3pm I was there, on the road, looking for the house number. 25, and there she was standing in the doorway wearing her dressing gown and smoking a cigarette.
She literally pulled me into the house, kissing me, taking my coat off and taking my bag. Like the spider with a fly in her web. She sat me down, chatting, brought me a tea and biscuits, and then lay on the sofa legs across me wrapping up her prey. Knees slightly ajar, I couldn't help but see her tiger-skin print knickers. But at the same time as being forward, she was eloquent and the conversation was intelligent. She knew how to please and handle, stimulate me. Why can't I find a girl like this, I thought?
She'd made me chili con carne for a meal, I was pretty pleased by that, and she'd even picked up some beer for me. It was Carlsberg Super. Boy, she's wanting to get me d*unk I thought. Dutch or Danish courage? Or perhaps she just doesn't buy this stuff much. Either way, she'd made an effort, something which always turns me on.
We chatted for a little while and she walked me upstairs to show me where I was sleeping. And where she was sleeping. She was very clear about that. Then as we came downstairs, she asked, do you want it now or later? It was absolutely clear what that meant but I said later. Why I'll never know. She didn't react though.
I sat back down. Her TV was on. And she came back with another cuppa. Just as she put it down, I stood up and put my arms around and inside her nightgown and restarted the kiss of months before. My hands around her body. Her skin was so soft and supple. It felt warm and like silk to the touch. Her kiss was a winner, and our tongues danced in a way I'd never experienced. Her nipples had hardened again, I could feel them against my chest. My cock was tingling and had escaped my jeans. Her breasts were not massive but fleshy, and my fingertips were being put to good use.
By now, I had lost my t-shirt and she had freed my cock fully from jeans prison. She rotated and I followed her as she lay on the sofa. She moved her tiger print knickers to the side, took her fingers round my cock as it approached, and guided me into her expertly. The help was not a problem. "Come on tiger ??", she said.
I began to thrust forwards and back gently. I now know that she was quite dry but the dry friction was pretty stimulating. And quite roomy, she'd had two kids, so now I know that it did feel different, more like a cave than a tunnel. "Fuck me Stevie", she said. "That's it, fuck me." I was doing my best. About 30 seconds of humping later, she began to make noises, she was cumming (of course, she wasn't but hey she knew how to please me). The faking actually triggered me and I made my last push into her dry cavern and exploded into her. After a few moments together, she got up and walked to the kitchen. She came back with a cigarette and said that she could feel me dripping all down her legs.
That evening, the time flew. We sat in, she stayed physically close to me, touching and lying on me, whilst I was on her sofa. As I watched football, she sat by me and loosened my jeans and started nibbling my neck. Then at some point, she put her hand round my shoulders, almost holding me like a baby and started rhythmically rubbing my cock. I turned to kiss her.
I was getting hard and TBH it felt uncomfortable, so I had to lie back and close my eyes. Her left hand rhythm was relentless. She pulled my head towards her chest. A mouthful of breast and nipple, and she pulled me more tightly into her with her right arm, so I had to suck on her now engorged nipple. It was like being breastfed and being wanked off simultaneously, a strange feeling and yes, my body and even mind was now completely under her control. I could feel myself building, my legs moving in and out against each other, and my lower body started to move, writhe in ecstasy. She was not stopping, my face pulled into her breast, her hand pumping faster, and the skin on my cock was near breaking point.
"Aah aah ahh", I was saying something garbled but too distracted to hear myself. A powerful surge rose from my body stem. Just at that moment, she stopped pumping, her arms relaxed, for the blink of a second. I recovered my breath. And then she restarted pumping me, and pulled me into her chest again. As she did this, waves of cum ejected from my cock, one reaching my neck. I'd never felt warm cum hitting anything other than my belly. One, two, three, four, five, six, seven, eight spurts. "You've got lots of stuff in there", she said, as she whipped me till I was empty, drained. Then she wiped it all up with tissues and lay next to me with arms around me, more relaxed, holding me with my face resting on her breasts, suckling me again. I was exhausted despite having barely done a thing, I could barely move.
"I'm a fucker, am I", she said? "What?", I said. She repeated, "a little fucker, you little fucker. A little fucker, am I?" Suddenly, I realised what I had said when I was getting close to exploding. I made a little laugh to laugh it off. And she kept saying it as we fell asleep there. "You little fucker….."
That night, I slept soundly in my designated bed.
She came to visit me in the morning and offered me her pussy. Offer isn't quite the right choice of word as she didn't ask. She just straddled my midriff, and then slid herself up and along over my chest and neck and onto my mouth, which she then rode and rubbed against. I push my lips and tongue around desperately. The thought of suffocation did hit me temporarily. She was clean, the smell and freedom to lick while she rubbed against my nose and mouth was in retrospect heavenly. She came from rubbing against my face, a moment I still dream of, and this time I knew that she had actually cum. Not a moment of fake in that five or fifteen seconds. Instantly after that, we enjoyed a slow and more relaxed missionary fuck, eye to eye, mouth to mouth. And this time she was moist and frictionless, and very submissive, and she took every drop from me.
At about 2pm, one of her friends came to the house. The friend was incredibly embarrassed. "This is one of my lab students", Jane said. "A very special one". Her friend then drove me and Jane to a bus stop nearby, and Jane and I said goodbye with a hug ?? before they drove away.
We had on and off sex for a couple of months that autumn, and then somehow it fizzled out as I became far too interested in an ebony BBW that I also met online. Oops!
**
By 19, I'd put those two fantasies to bed. Sadly I read that Jane died a couple of years ago. |
