Introducing Meghan: A Preference for Older Men

Meghan – not her real name – is an email buddy who has a killer sex drive and who enjoys reminiscing in writing about her sexual exploits. The Meghan Stories are all true and are compiled from bits and pieces of things she tells me in email messages. This first story is about her seduction of an older man she had chosen as the one to take her virginity.

So you can picture her in your mind, she is 5’4” and weighs 140 pounds. She is on the zaftig side, with a deliciously curvy 36D-28-40 figure. She has long, curly, darkish-blonde hair and a beautiful face. Her most characteristic expressions convey her intensely libidinous nature – sultry, a bit pouty, eyes half-closed. Most men would find her irresistible. No wait, you don’t have to picture her! Here she is, as beautiful as she is real.

And here is Meghan, in her own words.

I have had numerous experiences with older men. They knew how to treat me and made me feel like a woman rather than a sex object, a female receptacle for a penis, which is the way many guys view women. Older men may be no different in that respect – but they know how to take their time, to build up a woman’s desire, to make her feel that they are interested in all of her, not just in her body. It’s all about the art of foreplay, which boys do not know – and a lot of girls don’t either. I learned early and demanded it (in a subtle way) from my lovers.

I was a pretty early bloomer physically, as a little girl my body was shapely. My breasts developed early, my hips filled out. I knew I was going to have some serious curves! Boys looked at me all the time and some male teachers did too. I was a girl, still naive, but learning. Mom put me on the pill early because she knew I was a handful, didn’t know but guessed that I was sexually active. I had good grades in school, though, so was given a lot of latitude.

My first notion of what a penis looked like was the statue of Zeus at the United Nations. I was only a little girl, 7, but I was fascinated and couldn’t take my eyes off it. It looked HUGE.

As a teenager, I did hang out with boys my age a lot. There was heavy petting and kissing with some guys. I learned oral. Gosh I remember vividly the first time I did that. I was playing with him, obviously hard as a rock. I just leaned over and took it in my mouth. I heard a loud gasp from him as I kind of went up and down. After about five seconds BOOM! I got a mouthful. I didn’t know what to do so instinctively I swallowed it. It wasn’t horrible but wasn’t particularly pleasant either. He was apologetic and I was thinking “that was awesome!” I was learning to give pleasure and how that added to the power of a woman over a man. To me it was one more step up the ladder to becoming a woman. So that was a first for both him and me, I liked him a lot so we did it on a fairly regular basis. With that bond we became BF and GF for a while, not because of the sex but because I liked him. He wanted intercourse but I was afraid. I was about 14 1/2 at the time. I finally let him touch me one day when my parents were gone and would be away for hours. So we went to my room. We undressed unceremoniously and got into bed – my first time nude in bed with a guy. We held each other and kissed. He touched me and put his finger inside me, another first for me, but he wasn’t hitting the right spots. I moved his hand to where It felt good, which still didn’t work – but it felt nice! He got on top of me and I guess I opened my legs. He tried but I said no. In a teenage way not ‘going all the way’ kind of put a damper on our relationship. That became a point of comparison for me when I began to be involved with older men.

My first time actually fucking was with an older man. I was attracted to older men, but didn’t just pick some random guy. There was a relationship before – we were friends, though I was only 16 and he was 47. Definite jail time for him. But it was what I wanted, I enticed him. Under the law it would be statutory rape. But I felt in control from the beginning, that it was my choice and my initiative. If we’d been caught and he’d been prosecuted, I’d have told the world it was all my doing. I know that wouldn’t have saved him from being prosecuted. But in my mind it should have. Sometimes, as Mr. Bumble said, “The law is a ass – a idiot!”

I knew Mark thru sailing. I had sailed and crewed on another boat; but then that person sold the boat to start a new business. Mark knew when I became boatless, and he needed help on his boat – so he invited me. It was all pretty innocent at the time, geez his wife and kids were with us. So there was nothing between us at that point, I was just a kid from the dock helping out.

So I sailed with his family, his wife was polite but somewhat aloof. I guess I don’t blame her, she was an average looking woman, face and body and here comes Meghan, a large-breasted bombshell her husband picked up on the dock. But it wasn’t that way and I always covered up, T shirt rather than tank tops, etc.

I had never been with anyone sexually, hey, I was 16, just got my license, not exactly the woman of the world. But I was used to guys looking at me and knew what it meant. Even with his wife there I could feel his eyes on me. Plus, our conversations were often like we were alone together. This was kind of an extended foreplay I guess. I wanted an older man to teach me and I knew just by being around Mark and his wife that there was not much sex at home, the sex was bad, she was not willing or interested or all of the above.

So when we started going sailing alone I was ready. Our conversations were even better when we were sailing just the two of us – sometimes serious and sometimes very lighthearted. He treated me and my ideas with great respect, listening closely to everything I had to say and commenting on everything from a mature man’s perspective. He was a mentor as well as a friend and gave me insights into adulthood and taking responsibility for things.

He was very good looking as well. Over time, our conversations began to include banter that gradually became more suggestive. I’ve thought about this a lot, remembering how it went. I’m sure that there was nothing out of line with the things he said to me. In fact, I remember how I encouraged him, asking him how he liked my clothes, and posing for him in ways that were deliberately suggestive, if not downright seductive. One day I asked him if my body was grown-up enough for a particular outfit. I pursued the topic with him and got him to say I had a nice body. The memories of all of this are sweet to me. He was simply a nice, kind man.

On one particular day, when we left the dock I pretty much knew I wasn’t coming back as a virgin. I had planned how I would induce him to have sex with me. It started with the purchase of a very skimpy bikini without my mom knowing. She would never have let me buy it, and would have thrown a fit if she’d known I was going to wear such an enticing item on a sailboat trip alone with Mark. I had been thrilled at how it looked on me when I saw it in the fitting-room mirror – so sexy and grown-up! My breasts were pretty developed, round and firm, C cup. My hips and rear were pretty well filled out and I had a small waistline. I was curvy and womanly for a sixteen-year-old. And I had shaved the area that the bikini bottom didn’t cover. (I later grew one more cup size and am now, at age 31, a D. My hips and butt filled out a bit more too.)

We sailed a bit and he suggested we anchor at one of the islands and go for a swim, so we did. He had changed in the forward cabin and I did the same. He was tall and lean, and had a lot of chest hair, all white. I changed and walked out of the forward cabin, he looked at me and I took his breath away. My top was a skimpy halter, barely covering my nipples, with heavy string for the halter and around my back. The bottom was the same string with a thong back and a low-slung patch covering my front. I sat down, crossed my legs and said “do you like?” He had an erection, I could see that through his trunks. I was pretty aroused too and much of the sexual tension was my doing. I knew I wanted him, someone I knew and could trust. I pretty much made no bones about the fact that I wanted sex with him. I knew it was illegal but didn’t care. I had thought long and hard about this, and giving my full, deliberate, considered consent, no matter what the law said. I sooooo wanted to think of myself as a woman. The seduction of Mark was my declaration of being entitled to call myself one.

We went out into the cockpit (what a name!) and sat in the sun. We chatted, there was another boat anchored maybe 100 yards away. They were minding their own business and so were we. They couldn’t see much anyway.

He couldn’t keep his eyes off of my body and was checking me out every inch – my legs, the scrap of cloth over my pussy, my hips, my tummy, my breasts practically falling out of the bikini bra. I knew I had been tantalizing him with my words and actions and, since I know me, I knew I was soaking wet between my legs.

He wanted to go swimming, which was a good idea because it was hot. His boat had a swim ladder that hooked over the side rail. It only had two rungs under the water, so it required a hop into the water and a big “one leg over” to get back on.

He got in first and I followed, backwards, my virtually naked butt on full display. I felt his hand on my ass, guiding me, then to my hip. It excited me so much that I gasped. It was the first time he ever touched me anywhere, and here was his hand on my bare skin in a spot that was sexually charged. It was an intensely erotic moment, one that has stayed in my memory both for what it felt like and for what it meant.

In the water we played, “do you want to go nudie?” Those were his exact words. He knew what I wanted – and he was going for it. We were both treading water and he got his trunks off and tossed them on the boat. I reached around, tugged the bra string loose and pulled the halter over my head. He tossed that into the boat. My breasts were visible but his penis really was not because we were in the water. He pulled me close and my breasts pushed against him. I sighed, and he moaned softly. The feeling of my nipples against the hair of his chest was thrillingly sensual. My bottoms still on he turned me around, my back to his midsection and he pushed his penis against my ass. He snuggled my neck and held my breasts – I loved the way that felt! I was in ecstasy! He was hard and his breathing was loud. I was holding onto the ladder, tired from treading water. He took his penis and put it between my legs.

Chapter 1 »