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Hello Readers! Welcome to my latest story. It always makes me happy to share the darkest corners of my mind with some kindred spirits. If you enjoy this one, please look for more stories by me, Valerius Catullus on Nifty. In my world, you will find all the boys are bi or gay, and all the girls are completely straight. You will find lots of MMF, MM, MMMF, but no girl on girl unless one or both of them is trans. Nobody is much interested in pussy and vaginas are only involved in masturbation, procreation and double penetration. IF you enjoy what you read, do not be afraid to say so. I am always happy to receive messages from kindred spirits and I try to always respond.
pedicator@hotmail.com
International Waters
The greatest romance of my life began in no particular place, but rather on a ship on the high seas. Before the reforms, there was a time when the laws of the United States became a bit extreme for research, and so many scholarly institutions turned to ships beyond territorial waters to do their work. This was vital for some sciences, and very convenient for the department of Anthropology at Miskatonic University. I was a 24 year old grad student when this all started. I had been going on these cruises since I started college. It allowed us to study cultures in their home environment and avoid scrutiny.
Along with grad and undergrad students, there were also high school students in advance placement programs that fed into our school. Being a good looking guy in decent shape, I had always taken advantage of the situation. In my 7 years on that boat, I had taken at least 2 girls' anal virginities each summer, most of them trans occasionally cis. By this time I had acquired a reputation and had fellow passengers going for me, most of them much younger. None flirted as brazenly as Carlo, but reciprocating anything made me nervous. He was only 14 and new to the high school program. He had the sort of look where it was difficult to tell his age for a stranger. He had well developed muscles but without looking overdone like a bodybuilder. His strong arms, flat stomach and well developed shoulders were matched by well-turned legs and a round perfectly formed ass that drew the eyes of guys and girls alike.
I had almost immediately noticed his Mediterranean good looks as he eyed me from head to foot and smiled at me. He had gorgeous classical Italian features and unblemished olive toned skin, completely hairless above the waist. A shaggy haircut framed his face and looked good even when carelessly tousled. His undeniably masculine energy was a huge contrast to the girls, boys and shemales, all very feminine, that I had been dating and analling since I was 13 or so. Yet he exuded sex in such a way that made me curious. And when he was bold enough to grab my ass, touch my cock with his hand surreptitiously, or find an excuse to rub against me, I got a hardon in spite of myself and found myself wondering what it would be like to just give in.
To make matters worse, I had had no luck in my own efforts. One girl I went for turned out to be a Christian who refused to have sex before marriage. And the other one who did respond was afraid of anal and ontly wanted it in the pussy, which I have avoided touching for years. So I was already very frustrated before that night. We had made landfall to witness a native ceremony that involved annointing the participants with coconut oil. Afterwards, some of our crew had undergone a minor sort of oiling supposedly to experience the skin care benefits. Carlo was one of these and he spent the rest of the evening walking around glistening, with his shirt off and rather tight gym shorts on which revealed that he had a substantial package hidden in there.
I went to bed very unsatisfied that night and lay under the covers in my too-hot cabin below-decks for quite a while before I drifted off to sleep. At some point in the middle of that night, I thought I heard a door creaking and I halfway woke up. Next thing I knew, I felt a solid male form lay down next to me in the very narrow bed. I must not have slept very long because Carlo was still slick with oil as he just went for it and kissed me full on the lips and explored my mouth with his tongue. I was not used to this sort of forceful attack and despite reciprocating, I did pull away and try to protest a few seconds later. He hushed me by saying that my mouth said no but my body said yes, as he slipped off his shorts and got under the covers with me.
He must have heard rumours from past conquests of mine about how I slept naked, and now we were touching, both rock hard and ready to go. We continued to kiss and explore each other's bodies, and to my delight I found his package was even bigger than I had imagined. I threw off the covers and admired his 8 inch uncut cock and a huge ballsack that filled my whole hand. I told him I wanted to taste him, but he had another idea. I was sitting up and he pushed me back so he could straddle my legs, then I felt the thrilling sensation of him squeezing the head of my cock with his round, strongly muscled ass cheeks. There was still enough oil on him that my cock slid easily and quickly to his opening, where that exquisite resistance stopped me. But he was determined and pushed against me until I went in, impaling himself on me as he gasped in momentary surprise and a little pain at the sensation.
I didn't know it at the time, but my new mistress was an anal virgin. He had penetrated a couple of boys and one girl before but this was his first time bottoming. He focused on the pleasure of feeling full and started riding me, moving just a little at first, then going slowly faster and faster. This was new territory for me too. Instead of the soft tits of a woman or shemale or the soft, silky smoothness of a femboy, this boy was solid and masculine. Instead of passively letting me pleasure him like a girl, he was aggressively riding me and taking his pleasure, as I fucked him more and more roughly. His ass was tighter and more perfectly suited to my dick than any woman I'd ever been inside, and instead of a wet cunt to avoid while I entered her from behind, here was a beautiful hard, erect and uncut cock bigger than mine with a set of perfectly formed huge balls for me to caress and stroke, wishing I could have my mouth on them. The whole thing was very intense and very intimate but probably lasted mere minutes. Then, as our lips locked and our tongues intertwined, I fucked him harder and felt him start to shoot jet after jet of hot cum all over our chests and stomachs, as I simultaneously lost all controland filled him with the cum from my strongest orgasm ever up to that point.
We collapsed onto each other and soon fell asleep. I awoke with my hard dick between his ass cheeks and his lovely balls in my hand and we soon started again. The rest of that voyage was spent in a sexual fog, enjoying each other more than either of us had expected. BY the time we left for our respective homes, I was in love, though we had to be careful how and where we met because of the age difference. And every year in the summer, we would have our time on the ship.
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3 Years later
As time passed, our romance deepened. Every year we went on the Anthropology Department's voyage. I was now a research assistant at the university and Carlo was starting his last year of high school. We had been talking about possibly getting married after his graduation. Everyone on board knew we were a couple and the Captain even referred to him as my "lady friend". Despite our love and commitment to each other, we kept things interesting in the bedroom by sometimes bringing in friends for threesomes or more.
That year was marked by the unexpected return of an important figure from my past, Professor Sara Lindstrom. I had known her when I was Carlo's age and we had had a strange and unexpected romance then when she was a research assistant. Now she was a respected professor of anthropology in her early 40s just returned from a long time living in Europe. She was a strikingly beautiful woman with a surprisingly masculine energy to her. She was exactly the kind of woman I'm attracted to, tall enough to look me in the eye and not one for girly fripperies, makeup or talking around something she wanted.
"I've heard that you guys like to invite other people into your bed and I want to be next," she said without masking her intention at all.
"But you do realize those extra lovers are usually boys or shemales, right?" asked Carlo, confused about the whole thing.
"I knew we'd have to convince you", I explained to him, "but trust me when I say from personal experience that you won't regret this. She isn't like most women and you'll enjoy it too".
"I'm usually glad to have a girl join if she's watching and masturbating, or only lightly participating, but you want to go full out. You do understand my rules for that, right?" he asked, eying her inquisitively.
"Yes," she replied, "And I totally agree with it. I despise those women who think a man should have to work on her pussy for three hours to try to get her off. If you have that much trouble having an orgasm, you have a problem and you don't deserve one until you work through things yourself."
"Well, I'm glad to hear you say that," Carlo said with a pleasantly surprised look, "Becausewhen we fuck we move at a man's pace, Each of us reaches his climax when he can, and holds back only as long as he wants to. If a girl is involved, she has to know how to reach it on her own and in time. If we leave her unsatisfied, we wait a bit to recharge and then go again, only the second time, we fuck each other andf make her watch without getting any dick at all and she can get herself off or just stay unsatisfied."
"Damn, I think I'd get off even faster being teased like that," Sara said with a mischievous smirk.
"And then there's the fact that you have a pussy," added Carlo, as if this weren't obvious. I leaned in to stop him but he put up a hand and continued, "Liam here can't stand to penetrate a vag, and he refuses to lick one. He rarely even touches them. As for me, I don't mind using my fingers but I've never tried to fuck a cunt before. You do understand that we prefer ass?"
"I can't say I blame you," Sara replied with a shrug "Vaginas are disgusting things and lesbians should be banished from civilized society for what they do to each other."
"I don't get it," said Carlo with a confused expression, "I had heard that you lived with another woman for years, that Brazilian writer Giovanna Martins. Since she's about as feminine a girly-girl as you can find, I had actually expected you to look like a dyke. Are you just curious about dick or something?"
She laughed as she answered him,"Vanna? She has a bigger dick than most guys I've ever been with! She's extremely shy and discrete about it but she's actually a completely passable shemale. I can see you're surprised but why should you be? A born woman lacks the equipment to satisfy me and if I had to satisfy her, so do I. I can barely stand to touch my own cunt. Doing it to another woman would revolt me, and having to lick one would probably make me throw up.
"You know, I met that girl Tara that you guys used to date, and I've even seen her naked at a pool party. She's a good example of the sort of young female who would be seen as a sex symbol by a lot of people. I look at her and can admire that she's pretty, if a bit chubby in my opinion. I can look at some of her features and be jealous I don't have them, look at others and know mine is better. I might even wonder what it would be like to kiss her, but doing anything more would be a waste of time. She doesn't inflame my desire like she does to most men. Only a shemale can do that, and I'm a girl who can appreciate tits and curves. Most women can't and some might only feel a jealous rage or disgust looking at her.
"Now if we change the image to a young teenage boy of the same age, any woman with a pulse would be eager to ride his dick and most men would want to either do the same or fuck his ass. That is the true sex symbol. A man fucking a boy or two boys fucking is beautiful, erotic, passionate, and exciting to watch. Girl on girl is unnatural and gross and women only do it when social and political conditions make it worthwhile for them."
"Wow, you have me just about convinced," said Carlo, "but I did just have one more question about the age difference."
"My preference," she explained, "has always been for boys in the 13-25 age range. In fact, if you two accept me, Liam will be the oldest male I've ever done anything with, though I have been with a couple of shemales older than that like Vanna. You, on the other hand, are just what I normally look for."
We consulted and Carlo admitted to me that he was willing to try a new adventure. Something about this woman stirred curiosity even in him. We started kissing and slowly caressing while we undressed each other. She watched and quickly got noticeably excited. Soon her hand went between her legs and started moving back and forth slowly. We were stripped naked now and our cocks were already rock hard and ready for each other. We rubbed them together as we made out and she came forward, still fully clothed and took us both in her hands, alternately sucking my dick and his. She was very skilled for a woman and we both got more into it, enjoying the sensations. She had a jar of lube and quietly spread some on the fingers of both hands. Next thing I knew, she was fingering both of us, lubing us up and getting us ready for what came next. She stripped off her blouse, shoes and yoga pants and was now wearing only a matching bra and panty set. She has a more boyish body than almost any woman I've ever seen and as usual she is completely unshaven. I can see the hair under her armpits and on her stomach leading to a very hairy cunt (currently covered) and her legs have a decent growth of hair from her ankles to her knees, with a finer down on her thighs. None of it is very dark, it's a blondish colour like the hair on her head. She pulled me toward her on the bed so I ended up on all fours while we kissed, then she got up to kiss Carlo while she fingered my ass. Next thing I knew, I felt a slight but increasing pressure as he pushed the head of his huge uncut cock into me, trying to enter. I tried to relax and open up and soon felt the bulb of his cock head enter me.
He gasped as he broke through the resistance and stopped a second or two. I pushed back on his shaft, the better to enjoy the moment and soon felt him hit my g spot from inside. I moaned with pleasure, thinking that we should do this more often. He was the girl in the relationship and I had only been fucked twice. But even the first time I instantly recognized why women, bottom boys and shemales love taking it and why some ancient cultures worshiped phallus deities. I rode wave after wave of pleasure and felt her take my dick in her mouth. I gasped at the feeling of being pleasured from both sides. It felt so intense it only seemed to take a minute or two before I found myself shooting huge amounts of cum into her mouth while Carlo throbbed and filled my ass, then slowly pulled out. We collapsed on each other, kissing tenderly while she continued to move her hand frantically beneath her panties for a moment, and then shuddered as she came.
She then took our soft cocks in her mouth again and skillfuly brought us back to attention as we held each other and kissed. I leaned in and kissed her, unfastening and removing her bra at the same time. Carlo and I admired her looking like this. Her chest was as flat as a boy's except for the extra sensitive puffy nipples that were standing up. When I was with her all those years ago, she had been very slender and she still was. Other than a slight thickening of the thighs and hips and a bigger ass, she still looked more or less the same. We explored her body with our tongues starting with her lips and neck and going all the way to her feet, carefully avoiding her wet pussy, which had now soaked her panties and the hair that protruded around it. We pushed aside the back of her thong, leaving her cunt covered, and ate out her ass, applying vaseline with our tongues to get her ready.
I briefly stuck my cock between her cheeks to lube it up, then pushed Carlo onto his back, with his legs on my shoulders and entered his already lubed ass hard and fast. I fucked him hard, but slowly savoring every thrust. I had never been inside anyone with an ass quite as tight as his before and fucking him was always an exhiliarating experience. He screamed his pleasure and furiously stroked his dick. She was behind me, grinding against my ass and running her hands over my body, saying she wished he had a dick to fuck boiys with and cheering me on. As Carlo came all over us, she said she wished it was her getting fucked like that.
She had been very good to us and I could deny her no longer. I pulled out of Carlo before I lost control. I threw her down on her side, moved her thong out of the way leaving her pussy covered, and positioned my cock her at her back door. I went in and she gasped. Her ass was larger and looser than Carlo's and I knew I could hold back much longer with her. I told him he was tighter than her, and she jokingly smacked me and said it wasn't very nice but she wasn't really upset. She was enjoying this and pleasuring herself with her hand. I found I could pound her much longer than a boy and Carlo was getting hard again watching. I stood her up against a dresser and bent her over to keep fucking her. At some point the thong had snapped and fallen off and we were now all completely naked.
Carlo and I both ran our hands over her near perfect body and then he made her keep her legs pressed close together and stand up while I was still pounding her from behind. He got in front of her and gave her a deep kiss while playing with her nipples. He then thrust his huge hard cock between her thighs and started fucking her like that. When I was last with her, she had been skinnier, with a thigh gap and this would not have been possible. BUt her thighs had filled out nicely and he was loving it, while she was being teased by the massive member between her legs just below her wet pussy. We fucked her like that from both sides for a few minutes more and then I could no longer hold back and I filled her with jet after jet of cum from behind, while Carlo also pulled back and exploded in his third orgasm of the night.
She fingered herself a few seconds more then shuddered in climax and lay on the bed panting, with ropes of cum on her stomach, in her pubic hair and on her thighs. That was the first time we knew that we would end up keeping her around as part of our relationship and not just a friend with benefits. I had never pictured myself in a long term relationship with a woman who had a pussy, but that day the idea of a three way marriage first got into my head.