It is our anniversary and I sit naked on our bed. When I awoke this morning I was told to shower and to shave every inch of my body, to rub lotion and powder on myself so that every inch of me was soft and caressable. I have done as I was told; I am very obedient. By now the cherry red polish on my toes and my fingers are dry and shiny. My lips are glossed the same color. My eyebrows are plucked and shaped, my lashes curled, my face powdered, my cheeks blushed, my shoulder-length hair combed. I am so excited I want to touch myself, to give myself some relief, but I dare not. I hear the car enter the driveway, the engine die, the door slam. It seems like hours before I hear the house door open and close, then the footsteps on the stairs. I look in anticipation at the door as my lover enters behind an armful of packages.
The packages are dropped on the bench at the foot of our bed, forming a ziggurat leading to my lover's face. This is only fitting, for she is the goddess whom I worship. Her eyes sparkle and a broad smile parts her lips, glossed a deeper red than mine. Her eyes peruse me as she straightens up, obviously pleased with what she sees. She is wearing a navy blue pantsuit, a white shell, and navy blue pumps with two-inch stacked heels. A single strand gold necklace, a gold-band wristwatch, and small gold stud earrings complete her outfit.
She starts with the middle box. It contains a thong-and-bra set in lilac. I lay on my back with my feet in the air as she slides the panties up my legs as far as they will go. I stand and she pulls them over my hips, making sure of their fit in the crotch. She now holds up the bra.. I step into it, resisting the urge to kiss her thou our lips are only inches apart. She steps behind me to fasten the bra. She opens the next smaller box. It is a pair of seamed stockings, in lilac, and a garter belt, lilac flowers on a lilac background. She places the belt over the thong, closing it in the small of my back. I recline on the bed again with one leg in the air. She carefully rolls a stocking down to mid-thigh, making certain the seam is straight. Satisfied, she releases my leg as I raise the other; she repeats the process. She steps back as I stand so that she can adjust and fasten the straps of the garter belt. She is squatting before me and the fragrance of my perfumed skin conquers her. She buries her face in my crotch, pushing me back on the bed. My thong becomes darkened as her lip gloss covers it, until she finally pulls the crotch aside and licks me to orgasm. She continues to lick me until I orgasm again, then licks my juices until I am clean again. Placing the thong in place, she trails kisses down the inside of my thighs from crotch to the top of my stockings.
"See what you made me do?" She mockingly accuses me. I am leaning back on my elbows, looking at her. She was now kneeling between my spread legs, her hair mussed, her lips a smear, her makeup smudged. I merely smile. "You'll make this up to me later," she threatens, standing. She walks to the packages again, opens another one, and removes a full slip, also in lilac. I stand and raise my arms as she slips it over my head. It reaches just below my knees, with the bottom two inches being lace. The top of the bodice is lace, and there are lace bordered side vents three-inch deep on each side. She guides me to our floor-length cheval mirror so that I can see myself. Instead I look at her looking at me, her face a mixture of lust and pride, longing and accomplishment.
She returns to the boxes. She takes out a bateau-necked shell, in lilac. As I put it on, she opens the largest box. It is a traveling suit, burgundy. The full skirt reaches to mid-calf. The shoes came next, a pair of burgundy-and-white wing-tip pumps with three-inch heels. I sit to put on the shoes but she insists on doing it. She kneels before me, grasping firmly my ankle as she shoes each foot. Her hand travels up the seams to the back of my knees and I lay back, awaiting her pleasure. She moves her hands along the top of my thighs, pushing the skirt higher. At the top of my stockings she stops. I hear her breathing, then feel my skirt being pulled down. I look up to see her standing, looking at me. "In due time," she murmurs, "in due time."
She returns to the packages. From the second largest she pulls a handbag, burgundy, and hands it to me. Inside is a clutch with credit cards and identification for me as Joan and a make-up kit. Now only the smallest box remained. She hands it to me. I slowly unwrap it, careful not to tear the wrapping. It is a jewelry case. I open it, revealing a pair of pearl stud earrings and a single-strand pearl necklace. As I put them on, she combs her hair and fixes her make-up. She looks at me in the mirror, "We have a long drive ahead." I put on my jacket, grab my handbag and sashay downstairs to the car. She follows me, locking up the house. Turning, she is surprised to find me waiting by the passenger-side door. She comes over and opens it. "Milady," she intones, bowing slightly. I sit down, swinging my legs in ladylike. As she gets behind the wheel and starts the car, she turns to me and says, "Just you wait, my pretty," and pulls out of the driveway.
The road she chooses is a familiar one. This is the one we took on our first weekend together. A now paved centuries-old wagon road, it follows one of our state's rivers. A freight train of a seemingly endless line of cars slowly snakes its way along the opposite bank of the river. I sit with my legs crossed, right over left, reclined. She places her hand on my right knee, sliding it down by shin til she reaches the hem of my skirt, then caresses my leg to the top of my stocking. She traces circles on my bare skin, acting nonchalant as she keeps her eyes on the road. I mimic her, keeping my gaze out the window, wondering if the train will ever end. Her fingers trail down to the crack between my crossed legs. I raise my right leg, giving her access. As she fingers the skin of my left leg, I lower my right leg, trapping her hand. The car swerves as she has to use all her strength to pull her hand free. It takes both her hands to regain control of the car. I turn my head away to hide my smile, suppressing a giggle. She grabs a handful of my skirt, making sure to grab a garter strap. She pulls and lets it go, the snap causing a sharp pain. Now it is she who is smiling--no, smirking.
We drive for over three hours, longer than our usual daytrips. Finally, she pulls into the driveway of a former estate and we drive for five minutes through woods without any sign of buildings or people. As we round a curve, the old manor house appears, a large four-story edifice of granite and tall windows and chimneys at each end an two in the middle. She pulls into a stall for visitors. "We're here," she informs me, getting out of the car. She exits the car and comes to my side, opening the door for me and extending her hand. I swing my legs to the ground, take her hand, and stand. She closes the door behind me. She offers me her arm, and I take it. Together we stroll into the building. At the registration desk, she gives her name. For all of its nineteenth-century ambiance, this establishment is a paragon of high-tech efficiency. Behind the high oak counter computer monitors flash their messages as banks of TV monitors cover every inch of the grounds. The desk clerk asks for her car keys, and to my surprise, she surrenders them without a word. A look from the clerk and a valet materializes and escorts us to a booth in the dining area. It has a view of the grounds in front of the building: a flat, manicured park some three hundred yards deep. Ours is the only car in the visitors' section. The only people I see are workmen tending the grounds and valets. The valets all wear the same uniform: a long-sleeved dress shirt, necktie, a tight-fitting vest, pants. I notice the colors are different. The pants are all black, but the shirts could be either white, lavender, taupe, or black. The ties match the vests in color, but are either stripes, dots, paisley or print. And the vests are either red, gold, tan or gray. Our valet returns with coffee and crab meat salad, one of my favorites. He is wearing a white shirt, a gray tie with white stripes, and a gray vest. Looking around the dining room I notice all the valets wear white shirts, striped ties, gray vests. Only their ties are different. As I look around the room I saw a thirty-something woman wearing a black column skirt, a white blouse, a gray vest, a black-and-white pearl earrings and necklace set, and stiletto-heeled black pumps enter, carrying a clipboard. She made directly for us.
"I hope madam finds everything satisfactory," the woman inquires of upon arriving at our booth.
My mate looks at me inquisitively. I answer by stuffing my mouth with crab. She smiles at the woman. "Everything is satisfactory."
"May I sit down?" she asks, more a statement of her intention than a request. Almost imperceptibly she snaps her fingers and our valet reappears. The woman looks at him, then at a chair at the nearest table then proceeds to sit in the empty space outside our booth. The valet swiftly moves a chair beneath her. The woman sits without looking to see if the chair was in place. "I am Iris, lane mistress for Stepford Lane," she informs my mate, looking only at her. "I am sorry to interrupt your meal. I just wanted to introduce myself and let you know I am available at your convenience. When you are ready, please have the desk contact me and I will escort you to your cottage." Standing, Iris extended her hand to my mate. After they shook hands, barely touching palms, Iris looked at me, then back at her. "Your companion is truly beautiful," she stated, then turned on her heels and strode out of the dining room. The chair in which she sat was already back at its table. I look outside; our car is gone.
As we finish our lunch, she explains to me what the Estate is. For our anniversary she has booked a stay for a week, in which I will be treated as a woman of leisure on vacation at a spa. Well, we'll both be treated as women of leisure, but this vacation is really for me. I am to be known as Mrs. Townsend and she is to be Mrs. Randall. She has planned activities for me for each day in keeping with my status, while leaving enough time for me to pursue any other activity I might like. Finished, we stroll toward the foyer only to be met by the valet, who escorts us to a window bench while he informs the concierge to contact Iris. As we look out the floor-to-ceiling windows, we watched a valet drive up in a motor surrey, with fringe on the top. Just as my mate and I marveled at this modern version of a nineteenth-century carriage, Iris appeared behind us. Again, she addressed only my mate. "Your cottage is ready. If you would please come with me, we'll see if everything is satisfactory to you." So saying, Iris turned on her heels and strode toward the door. Like minions following their mistress, we followed her outside and into the surrey.
The valet drives pass the park, where a narrow drive leads toward the river. About every two hundred feet is a cottage, complete with picket fence, set away from the drive. Iris reviewed the conditions of our stay with my mate. My mate has selected a week's vacation for the two of us at the Estate. We are to have a cottage to ourselves. There was no usage of private vehicles at the Estate. If we want to participate in any Estate activities, we had only to call and a valet would pick us up, take us to the event, and return us to the cottage. Otherwise, our privacy was respected. We were not to intrude on the other guests, nor were they to intrude on us. Meals could be served at the dining room at the manor house, or could be sent to us. There were other services which my mate had requested which would be furnished at the appropriate time. The nature of these services was not revealed to me. After passing about five or six of the cottages, the valet turns into the driveway of one of the cottages with flagstone walks and driveway.
The valet scurries to the door of the surrey, opens it and extends his hand to Iris, then does the same for us. Iris leads the way up the flagstone walk, followed by my mate, holding my hand, trailed by the valet. At the front door, the valet again hurries to open it. Iris enters first. My mate lets me enter before her. The inside of the cottage is quaint. The door from the drive opens into a small kitchen. Next to the kitchen, filling half the cottage, is the living room. On the far side of the living room are two bedrooms separated by a bath. As we stand in the living room, I am not aware of there being two bedrooms. The entire cottage was furnished circa the 1950s, with pleated skirts on the couch, loveseat and chair, lace curtains, and other period furniture, including a lounger with a roll arm at one end. I swirl as I look around me, my skirt flying out and up. When I look at her she is beaming, happy that I am so pleased by her surprise. She comes to me, places her hands at the sides of my face and kisses me. The kiss is broken only by the sound of Iris clearing her throat. In our revelry we forgot about her and the valet.
"I'm glad the accommodations please you," she smiles. "If you need anything, please ring me." So saying she turned to leave, the valet again playing lackey and rushing to open the door.
As the door closes I again look around the room, unable to believe what I see. When my eyes come back to her, she is sitting--no, lounging-on the lounger, her head resting on the roll arm. She places one foot on the floor and the other along the back of the lounger. The invitation is unmistakable, without my seeing the come-hither look in her eyes. I go to her, dropping to my knees at her foot. Without further invitation or instruction, I began kissing her leg, starting at the knee, and raising her skirt as I kiss my way to her crotch. Her aroma signals her arousal before my lips feel the wetness of her panties. I trace the edges of her panties with my tongue as I caress her lower leg. Teasing, I try to place my tongue inside her panties without removing them, then continue to trace the outline of the panties to her raised leg, which I kiss from crotch to knee. I start to retrace my kisses when she grabs me by the back of the hair, pulls the crotch of her panties aside and mashes my face into her womanhood. I know that she wants to come at just this moment-no foreplay, no romance, just satiation. I tongue around the base of her clit in a continuous circle. Her legs tense with her orgasm as she pushes her hips into my face, pressing my face into her crotch. I rub my face from thigh to thigh, knowing her clit is too sensitive for even the soft touch of my tongue, but also knowing that she needs continued contact and movement against her pussy when she is in the throes of orgasm.
She runs her fingers through my hair as her orgasm subsides. Placing them at the side of my face, she pulls me up and kisses me, enjoying the taste of herself on my lips. Breaking the kiss she looks me in the eyes and then kisses my cheeks. Pushing me away she stands, takes my hand and leads us into her bedroom. We quickly undress, she removing everything, me leaving on my bra, garter belt and stockings. She sits on the bed, her legs over the edge, waiting. I drop to my knees again, knowing that I will be spending most of the afternoon worshipping her sex. She has her second orgasm as I wash her pussy with broad licks of my tongue from her ass to her clit. Her third orgasm comes with her legs across my shoulders as I tongue her perineum and kiss the bottom globes of her ass. The fourth comes as I wallow in the folds of her pussy. And after each orgasm, she pulls me up to kiss me, to share her aroma and her taste on my lips and tongue and cheeks.
Now she needs penetration. She breaks the last kiss and pulls me on top of her, leaning back on the bed, raising her legs until her knees are even with her breasts, but splayed, opening up the lips of her pussy. I enter her without guidance, my path eased by her juices. As my hips meet hers she contracts her vagina, locking me into her. I lay upon her, not moving, letting her body guide me. She wraps her legs around me, pulls my lips to hers, slipping her arms under mine to hug my shoulders. Running her tongue inside my mouth, she milks me with her cunt. I come quickly, having spent hours pleasuring her without relief. She continues squeezing me until I become hard again. She now nudges me in the small of my back with her heels, and I start to pump her. The rhythm is slow, with lots of grinding against her pussy. This is for her, not me. After many minutes she comes for the fifth time. I remain still, deep inside her, until her orgasm subsides. In her afterglow, I pump myself to my orgasm.
She hugs me to her as I grow soft. With a shift of her body I am out of her. She guides my mouth to her breasts. The nipples are hard, the aureoles flush. I take one into my mouth and suck hard, knowing that she can have another orgasm just by nursing me. It takes several minutes, but it comes, not as intense as when I ate her. I stop sucking and lick around the breast until she subsides. I repeat this with her other breast. It is now evening. We have been making love for hours and I have one last service to perform. I drop to my knees again and began cleaning the mixture of our secretions from between her legs. I do not touch her clitoris, for it is too sensitive, and this service is not to give her another orgasm. She lazily runs her fingers through my hair as I lick. Whatever our intentions, I cannot lick her pussy without her coming and just as I nearly finish she raises her legs, presses my face to her, wraps her legs around my head, and comes again.
Chapter 2
The next day I rise first and fix our breakfast. She tells me about my schedule. There is a morning class in deportment. She does not think I really need it, but there are some things about being a woman I have not perfected. Since we're here, why not take advantage of the class. The surrey arrives at 9:40 a.m. There are about five other transvestites in the surrey when it reaches us. The ride to manor takes about fifteen minutes, and the surrey picks up another four. I try not to look at the other women, but I do. Five of them are passable as women, one could use some work, and the other three would always be men in drag. I am very happy that I am the prettiest one. The class begins promptly at 10:00 a.m. Punctuality is one of the standards of The Estate. The class is conducted by a Mistress Ivana. She speaks in that clipped English accent affected by European ex-patriots living in the British Isles. I am unsure whether or not she is a real woman. She is quite taken with me, however, and uses me to model and demonstrate the various techniques and mannerisms of a true woman. The others are advised to walk like me, talk like me, sit like me, cross their legs like me, remove items from their purses like me, be like me. When the class ends, I feel like the Queen of England, no pun intended.
After the class, we spend the next half hour in the restaurant, practicing what we have just learned. Trying to be magnanimous--after all I am the queen--I try to help the three least passable ones to act like women without being camp. One of them resents this, as does two of the passables. At 11:30, Mistress Ivana ushers us into the surrey for the return to our cottages. She pulls me aside and compliments me on my look and my deportment. She hopes my stay is pleasant and that I would be returning for other weekends. I thank her, believing that this is just public relations on the part of staff. At my cottage, Mistress Ivana walks me to the cottage door, which she had not done with the others. She hands me her card and solemnly intones: "If you are not pleased with all the arrangements by the time your stay ends, please call me before you leave." I am somewhat confused by this statement, but keep the card. Mistress Ivana then exchanges air kisses with me and returns to the surrey.
Mrs. Randall has prepared lunch. This is very unusual. Since I began living as a woman, meal preparation has been one of my duties. She says that she has all the experienced with female drudgery to last a lifetime, but I need both the experience, and to make up for all those years being served by the women in my life. I haven't been served by the women in my life, not that there had been that many, but I enjoy meal preparation. The meal is simple: fruit salad, seafood salad, crackers, iced tea. I wonder if she even prepared it.
During lunch she asks about the class. I tell her everything, my elation various obvious in my expressions and mannerisms. She is very happy that I am happy. She explains that the surrey will pick me up at two p.m. I am to go swimming at the pool. In the meantime, she would like to cum again. We go to her bedroom where she undresses completely, then invites me to do the same. I am somewhat disappointed. I am enjoying The Estate, and would like to remain en femme as much as possible But she wants more than my mouth. She wants to feel my skin against hers, and soon we are locked in full body contact, legs entwined, tongues dueling, lips locked, hands all over each other. We move to a sixty-nine, but soon she is kneeling at my side, concentrating on my cock. She wants me to fuck her man-to-woman with an urgency I have not seen in her. She knows my cock better than I do, and soon I am a man again. She quickly flops on her back and pulls me on top of her. I enter her and ride her slowly, thinking she wants this to last. She wraps her legs around me and command me to ride her hard. I pound her as best I can, but rough sex is not my style. It is also not hers. Soon we are back into our regular rhythms, and both have a satisfying orgasm. Or at least I think so.
I shower and enter my bedroom. Laid out on my bed is a deep blue swim dress and matching beach wrap, a broad-brimmed straw hat, straw tote bag and cork wedge sandals. I finish dressing just as the surrey arrives. She compliments me as I walk to the door. I am the only passenger in the surrey. At poolside, I find a lounge chair and sun myself. Inside my tote bag she has included sunscreen, a make-up kit, a new book by one of my favorite authors and a swim cap. I decide to forego the sunscreen, diving into the pool and swimming its length after fifteen minutes. When I come to the stairs, a valet is there with a towel and a hand. As I remove the cap and shake my hair out, Mistress Ivana appears from nowhere and smiles at me. Very ladylike she comments, then strolls toward the field house. I gather my things and move to a lounge in the shade of the field house and read. After about an hour more, I realize that I am bored. There is such a thing as too much leisure. I tuck my hair into the swim cap once more and swim the length of the pool twice more. As I climb out of the pool this time, I spy Mistress Ivana at the balcony of the manor with a man dressed more stylishly than a valet, but somehow dressed the same. I cannot see his features clearly, but he seems to be well-built and nice-looking. They wave in my direction, I wave back.
When I come back from the pool she is sitting in the chaise lounge, reading. She looks up as I enter, smiles, and returns to her reading. In my room I find an outfit laid out for dinner: a royal blue sheath with matching high heels. A triple-strand gold necklace and gold earrings are on top of the dress. Affixed to the dress at the left shoulder is a silver pin, circular, about one inch in diameter, bisected by a wavy band. Next to the dress is a half slip, pale blue, hemmed in lace. On top of the slip is a garter belt and seamless stockings. The belt is pale blue, the stockings natural. Beside the slip are a bra-and-panty set, the panties full cut briefs, the bra padded, the set pale blue. I pull off the swimdress and wrap myself in a robe to do my make-up.
When I am finished and dressed, I enter the living room, fully expecting to find her similarly prepared. She is not. She has not changed--not her clothes, not her position, not her book, not her expression. She informs me that I am going out to dinner, not her. My date will be arriving in about fifteen minutes. Again I am confused, and again she explains. As an attractive woman of leisure, I will often be the dinner companion of men. I need to adjust to this part of my life, and I cannot if the only person I have dinner with is her. She has arranged for one of the escorts to take me to dinner, just as if I had a date outside. I should conduct myself as the lady of breeding and accomplishment that I had become. She would wait up for me like a worried mother, and expect complete details afterwards.
I was in shock. While I now knew I could live my life as a woman, and be accepted as such by the world, I wasn't as certain that I could pass as a woman socially. True, I have mastered the mannerisms and deportment, even the voice, but to go on a date with a complete stranger and carry it off? Well, not with a complete stranger. The man was a paid escort, and he did know I was biologically male. But this was a major step. She said that she promised to help me become a woman when we agreed to this lifestyle for both of us, and this was another step into womanhood. She was right. If I was to live my life as a woman, then I would have to experience dating as a woman.
At six sharp the doorbell rang. She insisted that I open it. At the door was a very handsome man, somewhat younger than me, and slightly taller than I was in my heels. He introduced himself as Jeff, and said I must be Joan Townsend. I stated that I was, invited him in, and introduced him to her. She rose and came over, and shook hands with him. She said she was very, very pleased to meet him, and hoped he would show me a good time. He replied he hoped he would too.
We left, Jeff driving a two-seater into Estateville. I had expected the dinner to be at the manor, since Estateville also serves the surrounding county, and travelers on the state roads. Jeff assured me that I had nothing to worry about, except maybe jealous women. We had dinner at the town's Italian restaurant. Jeff regaled me with the history of the county before The Estate was established. Afterwards, we walked around the town where he pointed out various landmarks and recounted their histories. As I became more comfortable with him, and confident of myself, I asked about him and The Estate. He had been at The Estate about ten months, and was chosen by my companion to be my date. He had seen me at the swimming pool. He was the man with Mistress Ivana, and was greatly impressed by my beauty, grace, and style. He took this occasion to complement me on my choice of clothing from the swim dress to my evening clothes. I did not ell him that my companion had selected them all. By 8 p.m., we were holding hands as we walked. By 9 p.m. he had his arm around my shoulder. This being a rural county, we decided to call it an evening.
Jeff escorted me to the cottage door, and I was unsure of what to do next. Before I had to decide, the door opened and she invited us in. She sat on the chaise lounge, indicating the loveseat for us. She asked several mundane questions about our date, like a mother questioning her daughter and her boyfriend after their first date. Jeff answered most of the questions, since I was not familiar with the places we went. After about fifteen minutes of bantering, she looked at me and asked, "Did you enjoyed yourself?" I answered yes.. She then looked at Jeff and asked, "Would you like to take Joan out tomorrow?"
"Very much, madam," he responded.
"Then you should pick her up at 7 tomorrow evening." Turning to me, she continued, "Joan, a lady escorts her date to the door." With this, Jeff stood and looked at me expectantly. I rose and walked him to the door. As I was about to open the door, she spoke again. "Joan, since you've enjoyed Jeff's company, and will be seeing him tomorrow, don't you think you should kiss him goodnight?"
I had never kissed a man before, and the dilemma I thought she had resolved she now imposed. I looked at her in bewilderment, hoping for some guidance, only to be met with a quizzical smirk, her knowing what I had to do and wondering how I would handle it. I felt Jeff's arms circle my waist and as I turned to face him I turned right into his lips. Somewhat startled by the contact, I instinctively drew back but by then Jeff was pulling me into his body, pressing his lips to mine. The kiss was not unpleasant, and I relaxed and let him kiss me, ending up with my arms around his neck. As he held me I could feel his cock growing in his pants. I broke off the kiss, somewhat surprised and very pleased that I could have this effect on a man. I opened the door and saw him out, leaning against it once I had closed it. Looking at her, I saw that the smirk had become a self-satisfied smile.
Chapter 3
When Jeff escorted me to the cottage after our second date, I didn't hesitate to kiss him goodnight. Only after we finished the kiss did she open the door and invite us in. I wondered if this was just coincidence or had she been spying on us. Again, we sat on the loveseat while she reigned from the chaise lounge The questions were the same as the previous evening: where did we go, what did we do, did we enjoy ourselves and each other. I was expecting her to tell me to escort Jeff to the door and kiss him goodnight when she shocked me with her next question.
"Jeff, would you like to fuck Joan?"
"Yes, madam," he answered, looking directly into my eyes. "I would like to fuck her very much."
"You know she's a virgin, don't you?" she continued.
"No, I didn't, madam," he responded. "That only makes her more desirable. I would be honored to be her first man."
He was looking directly at me while he said all of this. I was completely dumbfounded by this conversation. I looked from Jeff to her, hoping she was playing some sort of verbal practical joke. She wasn't. Turning her gaze from Jeff to me, she stated, "Joan, Jeff has entertained you for two nights now. He's taken you to dinner, dancing, and romantic walks. Not only have you said you enjoyed his company, but your kiss outside the door shows how much you enjoyed Jeff. A woman who has received such pleasure from a date is expected to return that pleasure, and that means more than a few kisses." I said nothing because I didn't know what to say. Jeff had a broad grind on his face, bordering on a leer. She rose and walked over to me, took my face in both her hands and kissed me. "Since this is your first time, I'll be with you." Turning to Jeff, she implored, "Remember, you are her first."
She took my hands and pulled me to my feet. Leading me by the hand, she took me into my bedroom, Jeff literally bringing up the rear. The bedclothes had already been turned down with the pillows placed in the center against the headboard. In the middle of the bed was a specially-shaped pillow, wide and high at one end, tapering and lower at the other. By the time we reached the bed, Jeff had already removed his jacket and tie, and was unbuttoning his shirt. She sat in the bedside chair, looking at me, waiting. Jeff had finished with his shirt and had removed it. He stepped behind me and undid the back of my dress. I removed my jewelry and my dress as he finished undressing. When I was down to my lingerie, I hesitated. She gestured that I should continue. I sat on the bed to undue my garter straps and roll down my stockings, taking them off along with my shoes.
While I did this, Jeff went to the night stand and opened a small case that was not there when I left. When he turned around I saw that he had a condom on his dick and a small packet in his hand. Naked, I climbed onto the bed on my hands and knees and waited for him. He came up behind me and I felt his hand on my ass. I tensed as something went into me, but it was too small to be his cock. Next I felt something cool and slippery and I realized that he had inserted some type of lubricant into my ass. Then I felt something larger enter and twist just inside of me. Jeff had placed a finger inside of me and was spreading the lubricant around my opening. Anal penetration had never been part of our lovemaking, and I found the feeling was quite nice. Jeff pulled his finger out and just as I expected him to penetrate me, he told me to lie down on the odd-shaped pillow, on my back. As I did so, he climbed onto the bed and positioned himself between my legs. The pillow raised my ass several inches from the bed while lowering the rest of my body. Jeff placed his hands underneath my knees and gently pushed my legs back toward my chest. Without touching himself he lined his cock up with my asshole and speared me with one thrust, going in all the way to his balls.
I had expected some discomfort, even pain, but felt only the fullness of him. He released my legs and lay full on top of me, kissing me deeply. He didn't move for about a minute, letting me adjust to him, then began twitching his dick inside of me. He placed his forearms on either side of my head, and began to pump, pulling out until just the head was inside then plunging back in to his balls, which I could feel bouncing off my ass. His tongue continued to ravish my mouth just as his cock was ravishing my ass. Instinctively I brought my legs up to give him better access, pressing my thighs against his sides. I wrapped my arms around his shoulders to pull him into me. The whole sensation--Jeff's kissing, the feel of his body on mine, the pistoning of his dick in my ass--was wonderful! I don't know how long Jeff fucked me, I was so lost in pleasure. Suddenly, he plunged deep into me, and stiffened on top of me. I knew he was coming as I felt the twitching of his cock as he shot his load. I felt fully like a woman, having drawn a man's seed with my body.
We had stopped kissing and our breathing was now ragged. Jeff began to kiss me again as his dick wilted. Giving me a long French kiss, he pulled out of me and sat on the side of the bed. I had been so wrapped up in being fucked-the anxiety, the anticipation, the act, and the aftermath-that I had forgotten about my mate. As I languidly looked around the room, my eyes locked with hers. I reached out to her and she came to the bed, sitting on the side opposite Jeff. "How do you feel?" she asked, taking my hand.
"Like a real woman," I replied. She bent over and kissed me. I grasped the back of her head and pulled her to me, hungrily kissing her back. She broke off the kiss, running her fingers down my body to my ass. Kissing me again, she inserted her forefinger, running it around my opening. The pleasant sensation caused me to jerk, my thighs closing and trapping her hand. She sat up and looked at Jeff, who was now standing by the bed.
"Jeff," she addressed him, "did you enjoy yourself?"
"Very much, madam," he replied.
She pulled her hand free of my thighs and placed it on my cock, which was lying flaccid against my stomach. She placed her palm against my balls and her index finger along the underside of my dick. "Would you like to fuck Joan again?" she asked. My cock jumped when she asked this. I looked at Jeff and saw he was becoming erect again. Looking at me, she stated, "It's best if you get fucked again right after losing your cherry."
As she spoke, Jeff removed another condom from the case on the night stand and dressed himself. She remained on the bed holding me as Jeff climbed between my legs again. As he placed the head of his prick at my hole she released me and shifted so that she was sitting by my head. "Just put the head in," she instructed him. He followed her direction, inserting only the head of his cock, then moving it in circles around my sphincter. She gripped my dick harder, giving me a finger massage. After a while, Jeff began stroking in and out of me, first shallow, then deeper. I raised my legs again and Jeff grabbed them, pulling them against his body. She bent over and French kissed me, now masturbating me, while Jeff was beginning to fuck me with full strokes. After several minutes I came, my come spewing all over my belly. Jeff kept pumping me for several more minutes before he also buried his cock in my ass and came.
She cradled my head in her lap, cleaning me with tissues while Jeff wilted a second time and pulled out of me. Jeff climbed off the bed and removed the second condom, standing by the side of the bed for further instructions. She looked at his spent manhood and concluded that he was literally shot for the night. "Jeff, we wish to thank you for your services."
"Would madam be requiring my services tomorrow?" he inquired.
"No," she responded. He looked very disappointed.
"Does madam mind if I get dressed?" When she answered no, Jeff gathered up his clothing and went to the bathroom. She kissed me again, lightly, and told me to put on a spa robe and my mules. I did as instructed, standing up just as Jeff came out of the bathroom.
"Escort Jeff to the door, Joan" she commanded.
I walked him to the door and gave him a kiss without prompting. He placed his hand on my ass, rubbing my crack. I could feel him rising again. I broke off the kiss, then thanked him for making a woman of me, and kissed him again. As I opened the door, she said, "Jeff, I will inform Iris how very pleased we were with your services." Jeff brightened at that and I ushered him out the door. As I walk to my bedroom, she opens her door fully, indicating that I am to spend the night in her bed. I am very thankful for her understanding and thoughtful way of completing my transformation into womanhood.
We spent the next couple of days lounging around the Estate-me swimming, us playing tennis, having lunch, going for walks. I even repeated some of the anecdotes Jeff told me. We plan on returning to The Estate on our next anniversary, and I will be fucked when we are there. It is the only time I become a complete woman as anal sex still is not part of our sex lives, and there is no man in our lives otherwise. I will always remember Jeff, and I look forward to our next anniversary.