Note to the reader: In this diary I will tell the true stories of my sexual encounters that have come about thanks to the internet. Some more precise details such as names and places will be left out to protect mine and others privacy, and also because they don't matter, but otherwise I will try to be as accurate and truthful as possible.
I'd been using the swingers' site for more than a year but still had not managed to fulfil any of my fantasies of bisexual threesomes. So it was a very pleasant surprise when one day I found a message in my inbox from a couple with a bi male. My excitement was somewhat lessened when I saw their ages: 49 and 51. I felt a bit odd about the idea of sex with people the same age as my parents.
However, I was feeling very horny, so I replied and we got chatting on MSN. They sent me their pictures and while the woman, Laura, was pretty good looking for her age, the guy, Patrick, looked like an old bloke down the pub with white receding hairline, less than flat belly and a face that reminded me of Howard from the TV soap Neighbours, right down to the glasses. But they also sent me photos and video clips of themselves with other guys my age, and the more I thought about it the less the age thing was a barrier, and in fact it turned me on.
The deciding factor though was when I sent them some photos of me crossdressing that I had taken when after years of dressing in my little sister's clothes I had finally bought myself a nice little slutty outfit from an online shop. They loved them! I had often fantasised about being a girl and getting fucked by an older guy, and the opportunity to act this out in front of his wife filming was too great to turn down, so I arranged a meeting.
The night before I spent about an hour shaving everywhere above the level of my stockings. It was over an hour's train journey to where they were, and I got increasingly nervous, contemplating getting off and getting the next one back several times, but I forced myself to continue because I knew I would feel stupid if I didn't. So with butterflies in my stomach I stepped off at the right station to see Patrick waiting for me.
"Hi, did you have a good journey?" he said smiling and extending his hand.
Forcing a smile, I shook it, smelling the reek of cigarette smoke, which grew stronger once we were in the car. I didn't speak much during the 20 minutes drive to their village, answering a few questions of small talk about university, feeling my mouth growing drier as I wondered if I was doing the right thing, if afterwards I wouldn't feel ashamed about what I'd done. Pat was nice enough though, so I thought if I did have second thoughts he would understand.
Eventually we reached the house, in one of those identical well-off suburbs that could be anywhere. Once inside he offered me a drink, which I readily accepted, hoping it would steady my nerves. I'd barely sat down when I heard the front door shut again and Laura came in. She was about my height with a good figure currently inside some jeans. Her hair was very light brown or dark blonde, with a few grey hairs, but apart from a very few wrinkles around her eyes they were the only indication that she was approaching fifty.
"Hi!" she exclaimed, and proceeded to engage in some jolly small talk. After he had finished a cigarette though, Pat interrupted.
"Jack is going to be Sarah for us today," he said, and I grinned stupidly.
"That's OK, you can be Sarah if you like," Laura said. "I need to change too, so I'll show you where you can get dressed."
I picked up my bag and followed her up the stairs, where she left me, indicating a spare room. Closing the door and pulling the curtains I realised that this was it, I was really going to go through with it. I stripped naked, including my glasses which I decided to leave up there so it would feel more like one of my fantasies and I would hopefully be less nervous, as well as because I wanted to look a bit different as my female alter-ego Sarah.
Unfortunately I had no wig, but I did have a garter belt with fishnet stockings, a lacy bra and thong set with tissue padding for breasts, a very comfy short skirt that just covered my bum, and a singlet with a bit of lace decoration, all in black. The set was completed with some black high-heeled shoes, and I shuffled awkwardly downstairs. Laura wasn't down yet; there was just Pat sitting smoking on the sofa, the curtains still open for any of the neighbours to look in.
"Wow!" he said as I came in. "You look gorgeous Sarah. Come and sit by me."
I picked up what was left of my beer and did so, finishing my drink while he began to caress my legs. I'm not sure if it was my vision being a bit blurred without my glasses, the alcohol, or just the relief of having got beyond the point of no return, but I began to relax a bit more. When he suggested we kiss, I agreed immediately, pressing my lips to his and meeting his tobacco flavoured tongue with my own. I was even starting to caress his belly when his wife walked in on us.
"Oh Sarah!" she exclaimed, sitting on the other side of me. "You look really pretty!"
I mumbled thanks and she began asking where I got my clothes. She herself was wearing a short, tight black dress.
"Right, we need to get you made up," she said and got up again. Come into the other room, the light is better."
I followed her and sat down at the table while she applied make-up to my face. Pat also came in, now with a video camera, and when Laura had finished he got me to go back in the living room, now with curtains drawn, to pose as a fully fledged Sarah for both his and my digital cameras. Once he'd got all the shots he wanted, including plenty of up skirt shots of my arse and the bulge of my balls squeezed into the panties, he passed the camera to Laura, and without too many more words exchanged, we resumed kissing.
By now I was getting into my role of a horny, slutty girl getting some extra-tuition from her professors, which was the scenario we had discussed online, although in the end it was barely mentioned. I let my hand creep down from his large soft belly to undo his flies and start feeling the prize. This done, I wasted no more time in kissing, sliding straight off the sofa while he pulled his trousers and pants down, and got on my knees between his legs.
He was completely shaved, so I started by licking and sucking his balls, massaging his shaft and feeling it grow in my hand. It was about the same size as mine, about seven inches long and nicely thick, so I couldn't resist it long. Soon I had it in my mouth and was sucking hard to his encouragement. He put his hands on my head pushing me down, the head of his cock pushing against my throat. It even went in a little a few times, but I almost choked so I pulled back and licked the shaft and circled around the tip with my tongue before sucking again, placing my hands either side on his large, soft, t-shirt covered belly to keep myself from going too far down.
Laura had come over for some close-ups, and passed the camera to Pat to get a look straight down at me, so I looked up into the lens, pulling back to smile and lick the tip before going down again, as I love it when porn actresses do that. Although I loved the feeling of his dick in my mouth and much preferred the taste of his precum to tobacco, I don't think I'd ever given such a long blowjob, because my mouth started to ache from all the sucking. So it was something of a relief when Pat announced that it was "Mistress' turn."
Laura had now taken off her dress to reveal a strange sort of underwear made just of black straps so her breasts were emerging through two triangular holes. As she took Pat's place on the sofa, I found I was less confident about what to do, not knowing what she liked. So I lay on top kissing her and stroking down from her neck, over her nipples and belly, then up from her knee-high boots. I decided this was silly, so I moved down, a little too quickly perhaps, licking her breasts on the way down, until I was once more on my knees between someone's legs.
I pulled aside the elastic strip that covered her shaved pussy to reveal the wrinkly mass of flesh that was her vagina. Tentatively I stuck my tongue in for a taste, licking upwards a few times, enjoying her juices, then, becoming more confident, I moved up from where my tongue was slipping into a hot wet hole until I felt the small shape of her clit. This elicited a moan and an arching of her back, so I began making circular motions here, occasionally succeeding in obtaining more moans, though I found it hard to resist the temptation to taste her wettest parts again.
While I was busy doing this, Pat was filming, but soon this seemed to be concentrated on my anus as I could feel him behind me pulling my thong aside. So it seemed it was my turn to sit on the sofa with my skirt lifted up while his big, short haired head moved up and down over my groin, my knickers held aside to free my balls and cock for the attention of his mouth. Of course it felt really good to have his warm wet mouth around it, and I was soon pretty hard, but I really wanted to have him inside me, so after he'd had a good suck I pushed him away and stood up.
First I pulled my skirt and knickers off, keeping everything else on so I still felt girly (and slutty), then reached for the condom and tube of KY jelly I had brought with me. Less than a minute of sucking was all Pat needed to get hard again, then I put the rubber on him and lubed him and myself up. We tried doggy style first, but I was too tight, so instead he sat on the sofa, now just in his t-shirt, and I squatted over him. This way I was able to control entry, just letting in the head at first, which stung a bit, so I eased up and tried again, letting a bit more in. Although it hurt a little, the pain ebbed away as I relaxed and the awesome feeling of a big dick in my arse took over. I began speeding up a bit, Laura filming everything, leaning back and closing my eyes.
After a while my thighs started aching, so I climbed off and turned around, kneeling over him. This way I used different muscles, Laura got a better view, and Pat could thrust up into me easier whilst playing with my cock as it bounced against his stomach. I lasted longer this way, but it was still tiring and not fast enough, so again I got off.
Now I was looser so I knelt on the sofa, leaning on the back with my arse out for Pat. He entered me from behind and began fucking me hard, his thighs slapping against my buttocks. Watching the video afterwards I can see his big arse pounding away, with just my stocking covered legs visible, accompanied by the sound of my moaning and crying out as I got really into it, feeling like a real slut. This wasn't just playing a role, it felt fantastic have his big dick slide in and out of my sphincter. From that position he got me to lie on my back with my legs up and lay on top pounding away and playing with my cock. Several times I thought I was about to cum just from the anal fucking, but I didn't.
He clearly thought the same about himself though, as he suddenly pulled out, ripping off the condom and shoving his dick in my face, just as we had discussed was my fantasy several times online. His cock immediately erupted, spraying cum in a long streak from my chin to my forehead, and then a more well directed one landed around my lips. I opened my mouth to received the third shot, most of which landed on my tongue, then closed it around his head to suck the rest out, dribbling a thick stream of semen out down my chin as my mouth filled.
As soon as he was done he pulled out and began sucking my cock again until I was hard, which didn't take long as I was so turned on from the taste in my mouth and sticky mess on my face and neck, not to mention from the previous action. Laura came over, now completely naked except for her boots, and I stood up, stroking her breasts and body again, Pat's lips still around my penis, then she got on the sofa with her legs open and beckoned me down.
I steered my cock down, brushing the slight stubble around her slit, then through the fleshy lips to the hot moist tunnel beyond. She wasn't especially tight, but neither was she loose, and after all that prostate stimulation I was pretty close to the end already, so only a couple of thrusts and her moans brought me over. I pulled out quickly, and fought it back, succeeding the first time, and after one more entry I thought I'd beaten it again, but ejaculated right on her slit. I thrust back in deep, pounding her mature cunt as fast as I could while I orgasmed, spurting load after load of my young spunk inside her, and continuing after I'd finished, until my dick became too sensitive and started to go soft. I pulled out and resumed licking, now tasting my own cum mingled with her juice, until she got up.
After a short rest to clean up, discuss my sexuality with Laura, and try on her dress, I found myself sitting on the sofa with my head on Pat's lap sucking his already erect cock once more. And again my mouth soon started to ache, so luckily he was eager to suck mine again too. This time I just lay back and let him get on with it, enjoying the new sensation of the tight dress on my skin and amazed at how soon he got me hard again. Adding to his oral work he inserted a finger in my arse, which felt pretty good.
However, Laura must have been feeling left out, so she suggested I fuck her doggy style. Whether I was just not hard enough, or simply unused to taking a woman in that position, I'm not sure, but I couldn't seem to achieve penetration. She was very nice about it though, and instead began sucking my cock. It was nice not to feel the bristle of stubble while receiving a blowjob for a change, and I did get pretty hard, so probably could have fucked her after that, but I didn't say anything. Instead Pat knelt next to her and they took it in turns until Pat took over completely, and she just held me from behind, her breasts pressed against my back while her husband sucked me to completion.
That was almost the end of the afternoon, except for trying on her evening gown for a short photo shoot, before it was time to get dressed and catch my train. Unfortunately in the following months, work and an injury conspired to keep me from meeting them again. In the meantime, they sent me a DVD of the session, and as far as I know they continue to meet young bi guys for fun, and I gave them permission to show the video to any they do meet. So if you get in contact with a mature bi couple, you may well get to see the "Sodomy of Sarah!"
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with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/crossdressing/webmeets-diary-ch-03.aspx">Webmeets Diary Ch. 03</a>