tagRomanceMaddie's Sexual Journey

Maddie's Sexual Journey


I finished my sophomore year at college and was waiting for my parents to pick me up and take me home for the summer. This is when the most horrible time of my life happened. Both my parents were killed in a major accident involving six cars and a semi rig. A couple others were also killed. It took hours for the police to identify my parents, try and contact the next of kin, and finally reach me by telephone. As I think about it, while it was a terrible time for me, they actually did a good job in managing to find me in a little less than twelve hours. I then contacted my two remaining grandparents, one on each side, and two aunts and an uncle. I finally made it home and then arranged my parents' funeral.

I also managed to identify the estate my parents left. My Dad was a lawyer and very successful, my Mom taught school. Apparently, even though we lived well, their incomes were largely used to support their and my day to day lives. The bank balance wasn't high, the insurance involved barely paid for the funeral and the house had a major mortgage and needed to be sold. I likely was going to need to get a job and get on with my life on my own

I'm a twenty year old girl. At the funeral, the last person in line to give their condolences as everyone left the church was a handsome man, perhaps thirty five, perhaps a little older. He gave me his business card and told me that my Dad was his lawyer and in a few days, when things settled down a little, he wanted to meet with me and make me an offer. The next day, I asked at my Dad's old law firm (which had insurance on my Dad but payable to the law firm, not me) about the man that gave me his card. He's in business, apparently extremely successful, with a net worth well up in multiple millions.

He calls me and I agree to meet with him. His coming to my home, or my home until it's sold, seemed the most convenient for both of us. My name is Madelyn Wright, his name is Harold Koslowski. Once we said our hello's and sat down, this is what he said to me.

"Maddie, you're a very good looking girl. I've seen your photos in your Dad's office for several years. You're more than attractive, you're patrician, you look and carry yourself well, as if you're from money and very well bred. I'm going to tell you something about me that I hope you won't repeat. I'm homosexual. That is, I find males attractive, not females. But I'm definitely in the closet, so to speak. None of my business associates are aware of my sexual preferences. I'm fairly sure that if my preferences became widely known that it would harm my business practice noticeably. Very noticeably. It would help me tremendously to be married to an attractive female. Someone that would, to all appearance, be my loving wife, go with me to a great many social and business functions. What I would like to offer you is for you to be my wife."

"Obviously, there would be no sex between us and you would have to be able to handle that. On the other hand, you would live a very luxurious life style and visit many places around the world, staying at the very best hotels. My demands on your time would be fairly minimal. You could arrange to finish your schooling, follow hobbies and so on as they fit into my schedule. I realize that I may seem like a predator, suggesting this so soon after your major loss. But I also realize that you're going to have to make a major life style change so this offer may ft in well right now. Please think it over and let me know soon."

I'm left pretty much in shock. We say a few sentences to each other in parting. And then I'm left alone, thinking about the offer. I would be a 'kept woman' like I've often read about except I wouldn't be trading my virtue for the support. The more I think about it, the fewer things I can find negative. I'm sure we should put it in writing, a contract so to speak. I assume I would have to commit to a fair amount of time, perhaps with some financial incentives involved. But it would be a lovely life in some ways, a lonely one I'm sure in other ways.

So, I meet with Harold and iron out all the details and we actually get married, at City Hall in a very quiet and unceremonial event.

I've now been married four years. I have beautiful clothes, I've been to a number of major cities in Europe and Japan with all travel definitely first class. I've finished my bachelor's degree. I've met a great many business associates of Harold's and attended literally hundreds of dinners and dances and parties with him. I've always acted fondly to him, hugging him in public, doing everything a loving wife would do -- in public but not in the bedroom. It's been an even better life than I imagined in some ways but definitely a lonelier one than I had imagined, too.

To keep occupied, I play tennis at a club we belong to, visit a gym regularly and take up riding again, going back to the same stables I first used when I was a teenager. The older man that owned it has either sold it or hired a younger man to manage it but my experiences are still as they were years ago with the only exception being my gradually becoming much better at horsemanship. I really enjoy it and am even thinking of getting into competitive dressage. The man that's now in charge, Jeff, is physically attractive but with the manners of a cowboy, sort of rough and unpolished. He's perhaps mid-thirties, probably six feet tall, and very fit in a sinewy way, like someone that's worked very hard outdoors for years rather than like someone that's a gym rat. I actually don't have a lot to do with him, although I need to do all of my scheduling through him. He's always been helpful although I'm aware that he eyes me up and down a lot as if I'm a favorite food or something but has never done anything overt to bother me.

He lives in an apartment that's directly behind the office at the stables. I've finished my workout for the day and need to schedule ahead so I go into the very small office to arrange things with Jeff. He's not there but I can hear some sounds from his apartment that's just through a door. Without thinking carefully I step through the door into a hall and down just a few feet. Sounds are coming out of a room and I step another few feet and look through the door. It's his bedroom and he and a blonde that I vaguely recognize from earlier meetings are both naked on the bed. I should back up and leave and do my scheduling later but it's as if I'm hypnotized or something and just quietly stand there and watch.

He's laying on his back, his very large erection sticking straight up. She's kneeling to his side, her one hand holding his cock and she's telling him what a gorgeous cock he has as she leans down and gets her mouth to it. She licks up and down, turning her head to get access and then gets her lips around the head of the large, dark red cock and starts to swallow it, making slurping noises. He just lays there and watches her .

I'm not a virgin. I had sex a number of times with my first boy, in high school, and then with a second quite often in college and then a third quite often, also in college. I enjoyed sex quite a lot. More than I thought, apparently. Since I always had it, I didn't realize how much I'd miss going without. These past years with Harold I've been limited to a few toys and my own devices. The result is that I can't tear my eyes away from the two on the bed. I slowly recognize the blonde. She's married and I've met her and her husband at a couple parties and I've talked with her slightly when our schedules overlapped at the stables. She's actually very attractive, a little older than me, perhaps close to Jeff's age. She obviously loves attacking his cock and I quietly envy her to a degree and watch as she works on it and obviously manages to get him to cum in her mouth.

As she sits back and lets go of his cock I watch it go softer as her pulls her to his side and begins working on her, kissing down her body, spending a lot of time on her breasts and then moving down between her legs. I can feel myself getting much wetter as he gets his face to her shaved pussy. It makes me realize than my pubic hair is trimmed quite a bit to allow me to wear some minimal bikinis but hers is the first naked, shaved pussy that I've ever seen. Jeff certainly seems to relish it. He's very active licking and fingering it. The way they are laying, their heads are in my direction. Her attention is to him but he can see me in the doorway as he looks up from his working on her pussy. He smiles and winks as he takes a moment away before getting his face and tongue back down to her.

I should have left earlier and definitely should leave now that he's seen me but I just can't. I must be close to cumming, just from watching him do to her what I now realize I want him to do to me. He must be good at it, she's really screaming with arousal. I bet I'm not that noisy. He just keeps working on her and she keeps on jerking around and yelling loudly and it becomes obvious that she's orgasmed. He sits back and looks at her, smiling, and then starts to slide up over her. I can see his cock, fully engorged again, dark red and seemingly too big. She spreads her legs even wider as the cock slowly disappears inside her.

Her tone changes but not the loudness. She lets him know that he's filling her up and she loves it. He looks at me and I can see the passion in his eyes as he pumps his hips. How much I wish it was me. I have to leave, I can't let the woman know I was there and saw her, I'll most likely meet her several more time over the years.

That evening, I manage to sit down with Harold. "I need to have some sexual activity in my life," I tell him. "I'm not happy being a nun."

"Maddie," he says, "I've learned to be very fond of you but I'm not going to have sex with you. I've been with a woman, years ago, even got engaged, but discovered I was much more interested in her brother than in her and we ended it. Besides, I'm now HIV positive, I wouldn't want to pass it on to you."

"Oh," I was surprised, "HIV positive? Are you telling me you're going to die? I mean, this is serious, isn't it?"

"Yes, it's serious but with today's medications I should last a long time. I didn't tell you to make you worry but to let you know that you don't really want to have sex with me or exchange any bodily fluids."

"What about sex with someone else? There's got to be some way to satisfy my very strong urges."

"I hadn't thought about this before. Yes, I guess if you can be discreet and not do anything that would affect your continuing to appear to be my loving wife, you can. You just have to be very careful who you're with."

"Well, I have someone in mind. The manager of the stables where I ride is having an affair with at least one other married woman. I'm fairly sure he would be interested in me if I made myself available. And I can't imagine he would have any interest in making it public in any way."

And so we agreed that I could give it a try, do what I want to do in order to keep me happy and continuing to perform as Harold's wife. So, the very next day I return to the stales and do a basic ride on a trail for about a half hour. When I get back I walk into the office where Jeff is sitting. "I've been riding," I tell him, "and would like to take a shower. Would it be all right if I used the shower in your apartment? And if you have the time, would you like to join me?"

He's a real man. He didn't jump up in a hurry, just smiled. "I've got the time," he says and slowly gets up out of his chair. As we walk into his apartment he puts his hand on the middle of my back. "Did you enjoy the show we gave you yesterday?"

"Yes, very much," I reply, moving on to the bathroom and beginning to unbutton my blouse. "I envied her, which is why I'm here now."

"Well then," he says, putting his arm on around my waist to halt my movement, "maybe we should wait and take the shower after we've worked up a sweat." I turn to him and smile in return and lean my face to him and we kiss.

"That was just an excuse to get us both naked," I say to him. I sit on the edge of the bed and pull my boots off, get up, finish unbuttoning my blouse and take it off and fold it slightly and put it on a chair. I then reach back and unfasten my bra, slip it off, and toss it on the chair. I bend slightly to pull my riding britches down over my butt and legs and step out of them and fold them and put them on the chair. Quickly, I push my panties down as I turn to watch Jeff push his briefs down and then we're both naked. His cock is up and ready and looking like the sexiest thing I've seen in years.

I kneel on the bed and across from me, he does, too. I nudge forward to him and he comes to me and we kiss. "You have an even better body than I expected," he says. I just smile and push him onto his back as I kiss him some more. Kneeling to his side, I wrap my hand around that gorgeous cock. As I lean down toward it, I move my hips and leg to straddle him and settle back a little to get my pussy to his face. As I can feel his fingers touching me, I lean down and get my mouth to this lovely cock. I use one hand to fondle his balls as I put my lips over the head and slip my mouth down over him, licking and sucking his delicious cock.

I can feel his tongue licking my clit, his fingers pushing into my vagina as I suck on his cock and play with his balls. We both go on with this for a couple minutes when I pull myself up and away from his mouth and as adeptly as I can, which is actually a little cumbersome since I hadn't done this in a while, I move around to face his upper body and get my vagina right above his cock. I drop enough to feel the head starting to force open my pussy lips. "Next time, we can do whatever you want but I really, really need this in me right now," I tell him as I slowly drop down more, feeling him push his way up into my vagina.

""You're really tight," he says. I just nod and keep lowering my weight, slowly feeling him move further and further into me. Finally, I'm sitting on him.

"It's been too long but you feel absolutely perfect in there," I tell him and start to lift a little before dropping again. It has been too long, over four years since I've felt this and he's about as big as any of the previous three, so I'm being really filled properly. I move up and down on him several times, enjoying every moment. I grin at him and lean forward, letting my breasts hang free and start to move my hips more back and forward, sliding on his very stiff cock. He gets his hands to my breasts, then forces himself up slightly to get his mouth to one and start sucking on my nipple.

"This is just so good," I say, sliding on him, feeling him move inside me. "I could do this all day." I last longer than I expected, sliding on him,sitting up and bouncing on him. I finally begin to feel my orgasm coming and I start to bounce harder and faster and it hits. I'm sure I screamed a little although I intended not to be as noisy as that blonde I saw him with, and as that really great feeling came over me I leaned forward, keeping him in me, and lay my body on top of him, the top of my head reaching up to his nose. He kisses me on the forehead.

I begin to realize that I came but he's still hard in me. He puts his arms around me and rolls me over, never coming out, and gets his knees up under him enough to start pushing that cock into me and pulling out and then in again, getting faster and harder with each stroke. It's been a long time since I felt this, like an orgasm that just keeps going on and on, it's glorious. I get my arms and legs up around him and hold on as he fucks me as hard as he can and he's in great shape and really bangs into me and I love it. I can hear myself grunting with each of his strokes and can hear his breath, almost panting, also with each stroke. It seems forever but probably was a couple minutes and I can feel him pushing hard into me and holding it there as he pumps his warm semen into me. "Jeff, thank you," I say, " I hope we do this often and that we're not done yet today, you're a great fuck."

"Missus," he says, "you're as good a fuck as can be."

"Maddie," I tell him, "Call me Maddie."

"Maddie, it might take a minute or so but, no, we sure aren't done for the day. I want as much more of you as I can get."

"My schedule is hard to predict, I need to be there when my husband needs me but if I can, I'd like to come back every day for awhile and then at least twice a week after that."

"I think we can manage to handle that," Jeff says, "You're a really good fuck."

"This time," I tell him, "I really needed you in me as soon as possible. But I love oral. I'd enjoy playing with your cock and balls for hours and have you eat me all night long. With a lot of fucking along the way."

"We can manage that, too," he replies with a grin. "Maybe it's time for that shower you wanted."

The shower is over a tub with a curtain to keep the water from the rest of the room. We have water running but in truth, we're not taking a shower, we're investigating each others bodies. He has me pressed to the wall while he mauls my breasts and sucks and then bites on my nipples. I have his balls and cock in hand and kneel down and suck him enough to make sure he's fully hard. He has one of my legs over his shoulder while he pushes his fingers into my vagina and then gets his mouth to my clit. We're both as aroused as we can be and I end up hands against the wall, my ass sticking back at him as he fucks me and fucks me and fucks me. I'm as aroused as possible and it lasts and lasts. I don't think I've ever been fucked for so long and it's absolutely glorious.

Finally, he cums and pulls out. He turns off the water and we just stand there for a few moments looking at each other, our mouths sort of hanging open in sated lust. I step out of the tub first and grab a towel and quickly dry myself." I'll be back tomorrow," I tell him. "About two in the afternoon if that's o.k.?"

"Yeah, see you then Maddie," he says. I dress and leave. I feel better than I had for a couple years. I'm almost ashamed that I feel no guilt about cheating on my husband. I mean, he gave me permission and it's not like he has any sexual claims on me. Outside I'm looking calm but inside I'm smiling, looking forward to repeating everything tomorrow.

I have truly great sex with Jeff every day for four days. Then two off and another good session. Then over and over, every two or three days or so for three months. No loving, no great romance but lots and lots of great orgasms. It even enters my mind that I should find someone else, too, to make sure that I get enough even if Jeff becomes unavailable but I don't, mostly just because things are going too well to bother. Then a glitch. I hadn't been paying attention but I slowly realize I was having no periods. I use a commercial kit from the drug store just to be sure. I'm pregnant. I need to talk with Harold about this.

Surprising to me, Harold thinks it over and decides that if having a wife helped him in business, hiding his real sexuality, then being a father would probably be even better. So I see a doctor and start treating my pregnancy as I should. And I continue regularly getting with Jeff for sex. Jeff doesn't mind at all. My stomach gets larger and larger and he still eats me and fucks me and I still suck him. I learn that it's possible to keep on enjoying sex almost until time for the birth.

It's a girl. I name her Jacqueline. She's terrific. Being a mother, I discover, is a full time job. Fortunately, we can afford all the help I need. I breast feed her for eight months and then start weaning her so that by a year, she's free of depending on me for food and is actually eating some solids. During this, I quit seeing Jeff for a couple months and get back on the pill like I used to use in college. I might like to have more children but I would just as soon choose when. Then I get back into my routine of having sex with Jeff a couple times a week. I'm still meeting all of Harold's needs, going to dinners and parties, traveling some. I continue to have great clothes. Many of the people I meet through Harold are very empathetic and happy for my having a child, even wonder when I'll have more. Some obviously have no interest in others, including me, but only in business and how to make more money.

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