I’ve often been asked the age of the youngest man I’ve slept with, which as of right now was twenty-two to my fifty-four years. But what about the other way around? What’s the biggest age gap as far as the man being older than me? The answer might surprise you, as I was a newly married young woman of twenty-five when I found myself sharing a bed with a married seventy-year-old man.
It went like this…
My husband and I started swinging about a year into our marriage while we were both U.S. Air Force lieutenants stationed in England at RAF Lakenheath during the mid-1980s. I discovered early on that my husband had a sort of thing (a fetish really) for much older women. I’m not talking about five or ten years older but rather twenty to forty years older. He didn’t want to date or marry such a woman; he just wanted to take her to bed. He told me that he lost his virginity when he was seventeen to a woman in her fifties, and that ignited his somewhat fetish. I didn’t know what to make of it at first but once I realized that it wasn’t something that controlled his life in the slightest, rather it was just something he relished now and then. I guess it’s comparable to enjoying a certain old, but expensive glass of wine now and then. He doesn’t need to have it, but if available, he will certainly not refuse a glass.
Anyway, as I said we were new to the world of swinging, and had been going to various private parties many miles off base, as swinging was a military crime (it was technically adultery). At a few such parties we met a much older couple named Pam and Les, who’d been in the swinging world for many years.
To my young self, Les and Pam were outright ancient. They were grandparents eight times over and certainly looked the part. At seventy, Les was actually in pretty good shape for his age. He very tall, solidly built but not fat, with a full head of gray hair, didn’t wear dentures, and actually looked quite distinguished.
On the other hand, his sixty-six-year-old wife Pam looked her age. She was short, a bit chunky, had a round face, and very prominent breasts. She tended to wear blouses that emphasized her cleavage, which I thought was overdoing it a little. I certainly would be upset if my grandmother exposed her breasts that way. But then my grandmother wasn’t a swinger, which makes a huge difference I suppose. Hopefully, she dressed differently when she was around her grandchildren.
Pam also had a happy and bubbly personality, was always smiling, and fluttering around. She was very flirty with my husband whenever we saw them at various functions. Knowing his interest in older women, I can see why my husband lusted after her and wanted to take her to bed as one of our swing partners. However, we had a very strict veto rule in place (we still do today) where either one of could just say no to any proposed encounter. We either both had to agree or it didn’t happen at all. That’s probably why he didn’t just come up to me and ask straight up if we could swap with Les and Pam, knowing what I’d get seventy-year-old Les in the bargain.
Up until then, when we swapped partners it was always with a couple that was fairly close to our own ages, certainly nothing over six or seven years older than us. So, what my hubby did was to slowly chip down my arguments before I even knew what they were. That’s how he did it to get me to try swinging, and he knew exactly where to chip away.
I suppose I should have felt jealous over all this work my husband was doing to get Pam into bed with him. Had Pam been a hot looking twenty-year-old then maybe I would’ve been. But she was a sixty-six-year-old, frumpy looking, overweight, gray haired grandmother. I knew in my heart that the attraction my husband had for Pam was pure lust and nothing more. And to be honest, I’ve felt the same way on a few occasions when we swapped with other couples and deep in my heart I was very glad to be paired with a particularly handsome man. Why couldn’t I let my husband do the same thing? How could I be jealous of her?
The real problem was that for my husband to take Pam to bed I’d have to go to bed with Les. I tried to find a way around it by suggesting that in this one case only he had my permission to take Pam to bed by himself. However, he told me that this wouldn’t work out, as it had been made clear to him that it had to be a straight swap. Later I found out that this was something that was negotiable – but my husband just didn’t push hard enough.
Eventually, I finally agreed that I’d do it, but he would owe me big time.
A few days later, my husband told me that he had arranged to meet with them for lunch at their home that coming Saturday, and if things worked out, we’d do the “dirty deed.” He half expected me to have changed my mind but I told him I was all right with it.
We arrived at their home that Saturday and had a nice lunch with them. They were quite chatty as we ate and told us a bit more about themselves during their early days of their marriage, which included serving in World War II in the Royal Navy. I was further impressed when he told me he’d seen combat while serving aboard several ships. Afterwards, we went to the living room to relax a bit and I was shown their wedding photos, and I was struck by how attractive they were when they were younger.
Pam was sitting next to my husband gushing over him like a schoolgirl while flirting with him. He seemed uncomfortable with her doing that while I was in the room with him. It was actually funny that he was embarrassed by Pam’s flirtatious ways, and yet by the end of the afternoon, there was an almost certain chance that they would be in bed together locked in a very intimate embrace.
I still wasn’t excited about my role in today’s activities, as I was to be given to Les so that my husband could have Pam. Not my idea of fun if I assure you. But if it was going to happen then I just wanted to get it over with as quickly as possible.
Pam must have sensed that I was getting antsy, because she suddenly suggested that we start. She then stood up, took hold of my husband’s hand, and led him upstairs to a bedroom. Les followed a few moments later, and escorted me upstairs to another bedroom on the other side of the hallway.
Once inside, he closed the door, pulled the curtains over the window, and sat on the bed next to me. As he did this, I found myself experiencing a sudden wave of extreme nervousness as the reality set in on what was going to happen. It seemed strange because I’ve been intimate with probably ten different men since my husband and I started swinging, and this encounter with Les was no different from the others. In fact, had he been my age I would be looking forward to this intimate encounter and would be eagerly waiting for my swinging partner to begin disrobing me right about now. But I suppose his age was a huge problem for me, and something I wasn’t sure I could get over. I just wasn’t attractive to Les at all and I doubted that I could do this. Les saw through my anxiety and tried to relax me.
Sensing my anxiety, Les said, “We don’t have to do this. I know that your husband probably pushed you into this and thinking about it now it really was unfair of both of us to expect you to go through with this. I probably should have allowed Pam to meet with your husband by herself as I’ve done with other guys.” Les then hesitated for a moment, walked to the door, and said, “I tell you what. Let’s go back downstairs and wait. We can have a cup of tea, and I’ll bore you with some more photographs.”
I felt better knowing that I didn’t have to do this, but then I felt bad for Les. Suddenly, a huge surge of compassion swept over me and I saw Les in a new light. Here was an old man who was letting my lustful husband have his way with his wife of forty something years, and he was gracefully letting me off the hook.
Suddenly I found myself saying, “I appreciate that. I really do.” I looked at my feet for a moment before looking up at him and saying quietly, “Let’s do it,”
“Only if you’re sure,” he said.
“I am,” I said.
Les smile, returned to the bed, and sat next to me. I put my hand onto his and squeezed.
Les proved to be a tender and slow lover. Though we didn’t kiss (one of my rules at the time that has since changed), he was allowed to fondle and kiss the other parts of my body to his heart’s content. He spent some quality time suckling my breasts, and it felt good. I mean really, really good. Up until now, though I’ve enjoyed other men fondling my breasts during sex, it usually wasn’t for very long. A few minutes of sucking, kissing, or squeezing until their attentions were drawn elsewhere on my body. But Les was different in that he paid real attention to them and took his time doing it. I was actually surprised at the surging pleasure that slowly began spreading throughout my body at his expert touch. It almost felt like an electric surge radiating throughout my body reaching even to my toes. Had he stopped there I would have left quite happy, having learned something new about my body and what gives it pleasure. It’s funny, but sometimes a takes a man to show a woman how her body works in the pleasure department.
As he continued his wonderful rubdown, I even began wondering if it were possible to orgasm through a breast massage alone. I think I found my answer though when I seemed to have run up against an invisible pleasure barrier that stopped just short of the orgasmic path.
Though I was nude except for my panties, Les was still fully clothed during this time. But once he was done with my breasts, I reached down and slipped off my underwear, and he took that as a signal that perhaps he needed to take off his own clothing as well. He then stood up, and began disrobing.
I really didn’t know what to expect as far as the state of his body as he was unbuttoning his shirt. When he took it off, I was actually quite surprised at the sight of his rather muscular chest that was covered in lots of chest hair. I’ve always enjoyed men with hairy chests, and Les didn’t disappoint me in that. It makes me feel like I have a warm and secure blanket covering me during sex. Plus the tingly sensations I get during intercourse really adds to my pleasure.
When his pants came off, I was even more astonished at his very flat stomach. Unlike most older men who tend to have beer belies, Less had obviously taken care of himself, or maybe it was just a natural thing for him to be in such shape. Whatever it was I liked what I saw and I suddenly began to look forward to what was to come.
The final surprise was his penis, which I finally saw when he slipped off his underwear. I’m not sure what I expected a seventy-year-old man to be sporting, but certainly not this as it was probably one of the thickest penises I’ve ever seen so far in my young life. It was at full erection, and it almost seemed out of place and not in proportion to his body. I’ve often heard that older men sometimes had problems with erections, especially in the pre-Viagra days, but this wasn’t the case with Les who proved different. I was a little concerned, however, with just how thick he was. I really wasn’t yearning to have such a large male member between my legs as I feared the pain it would cause going in. Well, it was going to happen one way or another, so I just put it out of my mind for the moment and concentrated on what was going on now.
Les returned to bed, played with my breasts for a bit longer before continuing his journey down my body. When he reached my pubic area, he opened up my legs so his head could fit between them and started giving me oral sex. Once again, Les showed that he knew what he was doing. I’m not exaggerating here, as it felt good. My husband is no slouch when it comes to giving me oral, but it took a lot of trial and error in learning where to lick and suck to give me pleasure. Les seemed to know instinctively what to do, or perhaps it was from all the practice he’s had over the years. Whatever it was, he hit the mark as his tongue worked its way towards my clitoris, and by the time he arrived, it didn’t take long for him to bring me to an orgasm. In fact, I was surprised at just how intense it was, and it actually made me cry out with a louder sound than I normal do. I’m sure my husband would have heard me through the walls, which meant that he would know that I enjoyed myself and couldn’t complain later that this was such a miserable encounter. Oh well. So much for my hubby owing me big time. Darn it, as I could have used a new purse at the time.
Les stayed in position and let me recover myself for a few moments before getting got onto his knees and reaching for the nightstand where he retrieved a bottle of lotion. He spread some onto his bare penis, and rubbed some between my legs as well.
We’d discussed using condoms earlier, and we’d agreed to forgo them here. For me, part of the enjoyment of sex was when the man came inside of me. I’m not sure why, but I love being filled with a man’s semen, and I often can orgasm during ejaculation. But today I know not using condoms that this was very stupid, and we certainly wouldn’t do this today unless the man is a very trusted friend. But we were young, stupid, and this was the 1980s. Thankfully, we survived and neither of us has ever had an STD to this day.
Once we were all lubed up, Les mounted me properly in the missionary position. He adjusted himself to take some of his weight off me, which gave me an opportunity to reach down so I could guide his penis tip to my entrance. I was worried about the pain of entry, and I wanted to make sure that he was at least planted in the right spot while he penetrated me. I was happy that he was still erect, however, as I half expected him to lose his hardness during the foreplay and not be able to recover.
Now that we were both in position, I laid my head back and waited for Les to begin. Les took his time and entered me gently. I felt the initial pressure of his penis head beginning to open my vagina entrance and for a moment, it actually felt good. But then a burst of pain hit me as my vagina opening began stretching more than it was used to.
“Ouch! Stop!” I said, and Les instantly became motionless.
We waited until the pain slowly subsided before telling him that it was all right to go deeper.
Les adjusted himself again and then proceeded to enter me properly now with his full penis length, and though there was pain it wasn’t as bad as that first surge. Once he was inside of me all the way he let me get used to him before he started moving. It was very slow and shallow at first but as my body fully adjusted to his size he got faster until he was giving me a rather sound pounding.
I’ve always enjoyed this part of sex when all is said and done and the man is now on top of me doing what comes natural. Just feeling Les on top of me moving with purpose deep inside of me was very enjoyable to me, but it’s also very hard to describe to men why I like it so much, even more than an orgasm. To be honest, if given a choice between the two, I’d take a good, hard thumping pounding over an orgasm any day of the week (though if I can have both then all the better).
After about five-minutes or so of intercourse, Les told me he was about to climax. “Where do you want me to come?” he asked.
“Inside of me,” I whispered into his ear. I was a bit disappointed though as I really wanted this to last a bit longer. I was also sort of hoping I’d have a second orgasm since I was feeling the first waves of pleasure building up deep within me.
He picked up speed and was really giving me some rather deep thrusting sex, and I felt my orgasm slowly building up. I wanted to come badly at this point and was hoping he wouldn’t climax too fast.
But then I heard Les grunting, and a few hard thrusts later, I felt his penis pulsating deep inside of me, which meant that he was releasing his semen at that very moment. So much for an orgasm.
Les rolled off me huffing and puffing and lay next to me. This really zapped his energy levels, as he was totally exhausted. Though I didn’t orgasm, I at least had his sperm inside of me, which was something I very much enjoyed. I stayed on my back with my legs up to keep his semen deep inside me for as long as possible (part of my fascination with sperm I suppose). As we relaxed, we remained silent. When I saw that he was recovered and was breathing normally again, I decided to get up. I was quite surprised at just how much semen Les had released inside of me, as it was leaking out of me like a faucet. I sort of assumed that someone as old as Les would have very little seminal fluids left to release. Luckily, there was a box of tissue on the nightstand, which I used to clean and plug up the leak between my legs until I got home.
Afterwards, I dressed and returned to the living room with Les where we found Pam and my husband sitting next to each other on the couch.
After a few minutes of polite conversation, we left and returned home.
I asked my husband how things went with Pam and he said that he really enjoyed himself with her. “Was it worth it?” I asked.
“Well, I’m glad I did it but I have to admit I probably wouldn’t want to do it again with Pam at least,” he said with a shy smile.
He then explained that Pam tried to control things way too much. Once the sex started it went all right, but she insisted that he pull out at the last moment and come on her belly rather than inside of her. As my husband has always hated doing that, he felt almost cheated at the end.
He asked about my time and I realized that he hadn’t heard my loud moan when I orgasmed during oral, so I was safe from being teased by him for enjoying myself when he thought I wouldn’t.
When we arrived home, I took a long shower and afterwards my husband escorted me to our bed (being in his 20s meant a fast reload time for my husband). Twenty minutes later, he was adding his own sperm to what was still left inside of me from Les and giving me the orgasm I almost had with Les.
We never met with Les or Pam alone after that. It’s one of those experiences that you are glade you went through it but don’t want to do it again.
Photo Credit: The movie Sleeping Beauty (2011). Director Julia Leigh