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My Experiences With an Older Man - Part Two

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So just to recap on my previous post.

I was 19 when I started sleeping with my boyfriend’s dad (sounds terrible, but there’s a whole story around that which I explained in the other post). He was an absolutely amazing lover, teaching me everything (and I mean, everything) about sex and how to make sure I made my own pleasure a priority.

I’d known from early on that Jeff was a swinger and that he used his business trips (he owned his own company and travelled the world to see clients) as opportunities to meet up with couples and groups for sex. This was in the days before the internet had taken off, so I am not sure where he got their details from (I never thought to ask back then), but he always seemed to have sufficient contacts to satisfy his enormous sexual appetite.

As I mentioned before, Jeff loved to talk dirty and discuss fantasies during sex, all the time encouraging me to do the same. Many of his involved sharing me, his young and increasingly horny mistress with others, in all variety of situations. I always found this erotic – especially when there was a bondage element included and he described me as being helpless whilst others took advantage of me – but I never expected it to become a reality.

We’d been meeting up for sex for over a year, and I was not far off my 21st birthday, when Jeff first made the suggestion. Sue, his wife, was away with the church, and Nick, my boyfriend (and Jeff’s son) was away with work on a training course. I’d skipped my afternoon university lectures to meet up at Jeff’s house.

We were having sex on the sofa – me bent over the side with Jeff pumping me hard from behind so that we could both watch the porn video he’d put on. This involved a FFM threesome and he asked me if I had ever fantasised about having a woman eating me whilst a guy was fucking me. I told him that I hadn’t, but that the idea appealed to me.

As we lay back afterwards, me tucked up in his arms and him playing with my nipples – over a year on and they were still just as fascinating to him – he asked me if I would like to meet up with one of his ‘couples’. They were in their 50s, he told me, and knew about our relationship. He was sure I would like them, as they would me. I wasn’t sure, as this seemed like a massive deal and a huge step outside my comfort zone, but Jeff continued to tell me how much he wanted it to happen and how good it would be, so I agreed.

I was still living with my super-strict parents at the time, but I gave them a story about going away overnight on a work-experience placement, and they accepted it. We also told them Jeff would give me a lift as it was near where he would be working that week, and with him being the husband of my mother’s best friend, they seemed happy with this arrangement. I dread to think what they would have thought if they had known!

We’d arranged to meet them in a hotel on the south coast, and Jeff had taken care of all of this, including the cost. He was wildly excited about the trip and talked non-stop about it as we drove. Even talking about this turned him on, and I could see the outline of his enormous erection through his jeans. He caught me looking at it and without saying anything, turned off the motorway and towards a country lane, where he found a remote spot and parked up. The sounds of his zip being undone and my seatbelt being undone broke the silence as I leant over and gave him a blowjob before swallowing all of the cum he deposited in my mouth.

We arrived at the hotel early evening and Jeff had certainly gone all out for this – I had never seen a hotel room quite so large or luxurious as the one he had booked. Being a successful businessman meant that money really wasn’t an object for him – he wanted nice things and he always got what he wanted. He’d also bought me several new sets of very sexy lingerie – a basque, crotchless panties, stockings – as well as a PVC French Maid’s outfit, which he asked me to put on straight away. It was super-tight, and almost pushed by 36C boobs out of the plunging neckline, which he loved. In fact, he loved it so much that had me sit on his face so he could eat me out whilst running his hands all over the shiny plastic, feeling my hard nipples as they strained against it.

Funnily enough, that was the only time we looked at most of the gifts trip, but they certainly got some use on other occasions.

After this, we showered, dressed and went down to meet his friends for pre-dinner drinks. Gail and Des were a nice couple and were friendly extremely from the first minute, both hugging me and kissing my check and saying how pleased they were to meet me.

As Jeff had said, both were in their 50s. He was about 6ft, with a stocky build, thick fingers (funny how that’s one of the first things I noticed!) and had dark hair, which was starting to grey at the edges. She was about the same height as me (5-7), also with dark hair and a rather voluptuous figure – overweight, but still attractive and with enormous (probably an F or G cup) breasts.

We started off with cocktails – a novelty for me, as my parents didn’t like me drinking, before moving to the restaurant for dinner. I wasn’t really that hungry – a mixture of excitement, nerves and general apprehension – but as the conversation and wine continued to flow, I started to feel more at ease.

After dessert, it was clear the others were all keen to get things moving, so we all went back to our room. Jeff ordered more wine from room service and put some music on. I sat down on the edge of the massive bed – as did Gail – and the two men sat on the sofa at the end, chatting away about their latest business investments.

“Sophie, you look tense,” Gail whispered as the men continued to talk. “Let me help you with that.”

She slipped off her shoes and got onto the bed, hitching her dress up so she could sit behind me and massage my neck and shoulders. She had a great touch and it felt really good. That, combined with the cocktails and wine, made me feel very slightly light-headed, although I was still fully aware of what was going on as her hands moved to cup by breasts through the lace of my dress. I felt her warm lips on the back of my neck, then her teeth as she gently nibbled on my shoulder. She began to increase the pressure on my tits, squeezing them harder and making me moan.

The men had now seen what was going on and stopped talking, watching as Gail expertly undressed me, kiss me all over as she removed my underwear. She paused briefly to take off her own clothes and I gasped as she unhooked her bra – her tits were even bigger than I had first realised with large nipples that stuck out like pencil erasers, one of which she held out towards me.

I had never been with a woman before (other than when a friend and I had learnt to masturbate whilst at a sleepover and had nervously touched each other’s breasts whilst doing so) and I was unsure what to do, but she pulled my head towards her as if nursing an infant and placed the nipple into my mouth. I immediately started to lick it and suck it the way Jeff had always done to me, which judging from the noises, she really liked. The guys also seemed to like what was going on; both had taken their dicks out and were stroking them as they watched me feast on Gails’ enormous boobs.

She then pushed me down onto the bed – quite roughly, I should add – and started to work on my tits. I’d always imagined that another woman would be really gentle, but Gail wasn’t – if anything, she was much more aggressive than Jeff had usually been – sucking hard and slightly biting them, causing a pleasurable pain to run through me. He had told me before that she liked to dominate in bed and I think the idea of having a younger, firmer female joining their sex-play made her even more determined to take control of events, letting me know that she was queen-bee.

She asked the guys to join us, which they happily did, shedding their clothes as they came to join us on the bed. It sounds like some sort of made-up fantasy, but this was really happening to me. I lay on my back, my legs forcefully pushed apart by Gail, who was hungrily lapping at my pussy, and a guy on each tit, noisily suckling as they continued to stroke their erections. Des was even larger than Jeff – definitely over 9 inches, maybe 10, and really thick – and I started to wonder if I would be able to take him.

I’m not sure whether through kindness because this was all new to me, or the need to be in charge, but Gail told me to sit back and watch her demonstrate one of the many ways a woman can please two guys at the same time. She mounted her husband’s dick, clearly used to the size and taking it all in one go, and started to ride him hard, her ginormous tits bouncing everywhere as she did. She then gestured for Jeff to stand in front of her so she could suck him off at the same time. I felt a stab of jealousy that she knew him as well as I did, and that he was so comfortable just sticking his cock into her mouth without preamble, but as I took in the details of the erotic live-scene I was witnessing, that soon passed.

I think Gail had planned to have Jeff shoot his first load in her mouth, but he had other ideas. Laying down next to Des, he had me fuck him reverse-cowgirl so that she and I were facing each other and could play with each other’s tits, which we did. As Jeff became hornier, he always became more dominant, so it didn’t surprise me when after a few minutes, he told me to get on my hands and knees.

After a year of sex with Jeff, I had come to love being dominated, and even now, I don’t think there is another position that makes a woman feel more owned than doggie-style. From that first moment you feel the guy’s cock-head pushing against your entrance, forcing its way past that initial, tight section, you know he’s in charge and he’s going to give you a pure, animalistic fuck. You don’t make love doggie-style, you fuck. Whether he holds your hips to pull himself deeper, plays with your tits to remind you he owns them too, or grips your neck to show how much control he has – it’s heaven. I know some women have an issue with this, and each to their own, but for me being spanked, having my hair pulled and knowing that at any moment, my pussy will be filled with cum and I will feel every contraction in minute detail is pretty much as good as it gets.

So there we were, him fucking me from behind treating me to a little clitoral stimulation with one hand as the other squeezed one of my nipples as we watched Gail have her first climax aboard Des’s monster-cock. She was loud – louder than me, but before she had fully recovered, she had already slid underneath me and replaced Jeff’s fingers on my clit with her tongue. He was getting even more turned on, and as I looked down between my legs, I could see she was playing with his balls and ass as well as pleasuring me. A few times, he pulled out of me and thrusted into her awaiting mouth, letting her lick off my juices before using her hand to guide him back into my soaking pussy. Des has been watching this and now decided he wanted some action too. He stood at the end of the bed, next to my head, his erection in his hand and pointing towards my mouth.

When I look back now, I marvel at how no-one has to speak during group sex – everyone seems to know what everyone wants and just does it without needing to be asked. I willingly took him in and started to suck. I couldn’t use my hands on him, as I was still being fucked, hard, by Jeff, and needed to use my arms to steady myself. I could taste a musky flavour on him that must’ve been his wife’s pussy juices and wondered if she was getting the same taste when Jeff’s dick slipped between her lips below me. I felt Des’s thick, slightly rough fingers find my nipples, pinching and tweaking them as he pumped my mouth, and the combination of this, Jeff hitting my g-spot and Gail lapping at my clit pushed me over the edge. I had a huge, intense orgasm, although this was largely muffled by the enormous cock invading my mouth.

As I recovered, everyone switched around. Neither of the guys had cum yet (I wonder know if they had taken something beforehand) and both were keen to see some more action. Gail begged Jeff to fuck her, which he did, spooning her from behind whilst fondling her tits. Des told me how sexy he’d found it watching me ride Jeff earlier, and asked me to do the same for him. Facing away, I mounted him and set about the task of fitting his cock into my tight pussy. Eventually, it slid in and I enjoyed the slightly painful feeling of him stretching me as I raised myself up and down on him. My tits began to bounce as I gained momentum, so knowing that everyone was watching me, I began playing with them, squeezing the flesh and flicking the nipples as I came on top of Des.

After this, he rolled me over and tit-fucked me, making me hold them together as he thrust between them. I found it hard to understand at first why he would want to do this to me when his wife’s boobs were so much bigger than mine, but the I remember what Jeff had told me about older guys fantasising about young, perky tits. It was no surprise then when Des climaxed spraying jets of cum over my cleavage and neck. What was unexpected was when Gail pulled me towards her and began licking her husband’s sticky juices off me, paying particular attention to my nipples, which she again sucked hard.

Feeling completely caught up in the moment, I slid downwards and licked at her clit as Jeff continued to fuck her from behind. It was so sexy, the sight, the sounds, the smell – everything going on around me was a massive turn on. Soon after, they both came and we all sat around, exhausted, for a while, before they announced they were tired and going to bed.

I feel asleep quickly and must’ve been out for a good few hours before I became aware of a damp, pleasurable sensation on my breasts. Jeff was lying in front of me, suckling one, then the other, back and forwards. I was still wet from the earlier session and him doing this had me practically gushing, but I was still tired and wanted to go back so sleep. I rolled over onto my other side, expecting Jeff to do the same, but he had other ideas. I felt some movement and heard a noise which jolted me awake: he was opening a bottle of lube, which I knew meant only one thing.

I tried to wriggle over to the other side of the bed, but I wasn’t quick enough. Jeff was quickly on top of me, pinning my legs with his and holding my arms with his hands so that they were pinned above my head. He didn’t try to penetrate me straight away; instead, rubbed his very-hard cock between my thighs as he kissed and nibbled my neck and shoulders, whispering the obscenest fantasies in my ear as he did. In spite of myself, I started to get aroused, but I knew that he loved the play-fighting as much as I did, so I pretended to struggle and pull myself free. This brought out his dominant side, and he spanked me, hard several times whilst trying to restrain me. In the end, he used one of the stockings bought the day before to tie my hands together and secure them to the bed frame, and another to blindfold me.

Once he had me in position, he started to lube up my ass with his fingers, preparing me for the next stage. Then he moved away, and I heard a strange noise coming towards me, which I realised was a vibrator. Jeff pulled me up on my knees, my hands still bound to the bed frame and slowly inserted the toy into my pussy. He was going to DP me, something he had often fantasised about doing, but presumably felt that Des had not been the right go to join us. With one hand holding the vibe in place, he used the other to insert his erection into my tight hole. Taking it steady, he penetrated me and started to thrust.

We’d had anal sex several times over the year, but I had never orgasmed during this and still found it a little uncomfortable, especially when he got more turned on and fucked me harder.

This time was different.

The tingling sensations in my pussy were incredible, and as Jeff built up momentum in my ass, so he increased the speed of the vibe. He continued talking graphically, reminded me how vulnerable I was and how much he wished there was another guy underneath me. My ass was his, and his alone, he said, but a guy in my pussy with his mouth latched onto my nipple, squeezing the surrounding tit like he was trying to milk it would be awesome.

Then he described a third guy being there, his cock so far down my throat I’d be gagging, his hand playing with the spare nipple the other guy wasn’t feasting on, other hand in my hair, forcing me onto him….

At which point I came. Hard. My pussy muscles contracting around the fiercely buzzing vibe and my ass contracting around his dick, so tight that it instantly made him come too. I remember falling back to sleep, exhausted but satisfied and wondering if I would ever experience a climax at that level again.

We didn’t see Gail and Des the next morning as we needed to get back, but we could hear them fucking next door as we were leaving. I never saw them again, and I stopped seeing Jeff when I moved away after graduating, but I will always be grateful to all 3 of them for the appetite they have given me to try swinging again one day.

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