Postcards from THE ESTATE
Guy and Ellen
Part VI
Mr. and Mrs. Harris watched from their table as Guy and Ellen left the terrace, thinking the couple just a man escorting a beautiful woman in a revealing dress. A few minutes later they saw that man with his arm around the woman's waist, holding her tightly to him, walking across the lawn between the Manor House and Guest House II. They saw the two stop twice to hug and kiss, her arms around his neck, his around her waist and on her ass.
For the first time since Nathaniel was 15, Ellen thought about losing her virginity. Not if, or how, or when, or with whom, but definitely this night with this man. The only question that remained was how. That first kiss on the way to Guest House II, her second with a man, was different than her first. Like the first, it took her by surprise, Guy just turning her in his arms and kissing her. Unlike the first, she opened her mouth and savored it. This time she noticed the difference in kissing when you're the one wearing lipstick rather than your date. The third kiss found Guy's arousal pressing into her, and she responding in kind.
'Ohmigod!' she thought again. 'When I get out of these clothes I'm going to have a hard-on!' The thought remained with her during the rest of the walk, the entrance into Guest House II, the elevator ride to her suite. All the time she was trying to think of some way not to be aroused, with the opposite being the effect. Like trying not to think of a white horse, after some one tells you not to think of one.
At the door, Guy kissed her a fourth time. Stepping back, he looked at her with pure lust as she took out her door card and slid it through the slot on the keypad. She stepped inside expecting Guy to follow, surprised when he stood outside the doorway with an expectant smile. She then remembered what Brenda had said. Reaching out and taking Guy's hands in hers. "Would you like to come in, Mr. Hughes?"
"Yes, I would, Ms. Sharpe," he answered, stepping across the threshold.
He closed the door and took Ellen in his arms in one motion, kissing her a fifth time while unzipping the back of her dress. He stepped back and began undoing his tie, his look indicating that she should remove the dress. She did so, letting the garment fall at her feet. Guy had removed his tie and jacket by then, dropping them into a chair. He took her into his arms again, kissed her, then guided her into the bedroom. Running his hands into her panties he grabbed her cock and held it firmly as he pushed the panties down her legs. Guy massaged it until it was stiff, then turned her around and pushed her to the bed. She sat there, her panties hobbling her just beneath her knees, her dick sticking in the air. Her discomfit at having a raging hard-on registered on her face.
"It's perfectly normal, Ellen," Guy said as he finished undressing. "It shows that you're glad to see me, so to speak. A lot of sissies refer to their cocks as their clits. I think that's rather silly. We are what we are. While you make a beautiful woman, anatomy is anatomy."
What Guy did next shocked Ellen. As he spoke, he had finished undressing. He took a condom out of a box on the nightstand, a box Ellen was certain was not there this morning, and placed the rubber on ... her! Not just placing it on her, but pushing it down her cock with his mouth. This placed him on his knees with his head in her lap. As he finished, he dragged his tongue along the underside of Ellen's cock.
Looking at her he asked, "Haven't you ever eaten pussy?" Ellen nodded. "This is no different. As a man, you go down on the woman you're making love to. Only this time, you're the woman."
Guy then removed Ellen's panties. He then pushed her back so that she was laying on her back. He spread her legs and kissed her balls, running his tongue over the sack and along the perineum. No woman had ever done that to Nathaniel. As Ellen enjoyed the feel of Guy's tongue between her legs, she wondered if the sensation was do to a mouth down there, a man's mouth down there, or the fact that the region had been depilated and softened and sensitized. Reflexively she grabbed Guy's head, wanting to keep him down there.
This was the one action which Guy disliked when going down on someone--man or woman. He was good at oral sex and there always came that point in time where his partner would grab his head and hold his face to their crotches as they experienced orgasm. Guy knew it was because he had given them pleasure, and it should have been a compliment. But it also deprived him of freedom of movement. And lack of freedom in sexual matters--and in most others--was something Guy did not like.
He reached up and took Ellen's wrist firmly in his hands and removed Ellen's hands from his head, continuing to lick her balls and perineum. He placed her hands at her sides, then unfastened the garters from her stockings. Rolling each stocking down to her knee, he kissed her skin as he exposed each leg. This was the one thing about sissies--and THE ESTATES's Transformation Services--that kept him coming back to both: that silky smoothness that a denuded man's leg has. Soft like a woman, yet firmer. It was a sensation he found nowhere else. Even women who worked out and were athletic did not have this same quality.
Ellen also experienced this difference. The way Guy removed her stockings was like having a second skin removed. As his mouth and tongue immediately followed the skimming of the nylon, she experienced a series of sensations: the release as the stocking was removed, the feel of the air on her bare skin, the feel of Guy's breath immediately following, then his lips, then his tongue, then his beard or mustache. She found she enjoyed feeling the coarseness of his hair against her skin. Reflexively she grabbed his head again, wrapping her legs around it.
Guy placed his hands on the inside of her thighs and pried them apart. He stood and clothed his cock with a condom, looking down at her sprawled figure. Ellen looked at him with lust filled eyes as he lubricated himself, languid on her back. He took her right leg and pushed it toward her until her knee touched the nipple of her breast. Reaching between her legs, he took the string of her tampon and jerked it out. The sudden removal caused her to gasp. Placing the ankle of her leg on his shoulder, he sank his knees into the bed, bringing his cock to her asshole.
The moment of truth was at hand. This was what this weekend was all about. Three years ago, Nathaniel would not thought about wearing women's clothing. Two years later Ellen was born. Six months ago Ellen was resisting even the thought of sex with a man. Six days ago she was actively considering it. Six hours ago she knew she would surrender her virginity this night. And now it was about to happen.
Guy leaned forward, placing his weight on his hands. He kissed Ellen, who returned the kiss, their tongues dueling as she placed her arms around his neck. She felt the bed sink beneath her as he laid on top of her. When he shifted his weight from his hands to his forearms she realized that he had entered her, the hair on his balls tickling her hairless ass. She was now a woman. Guy's woman.
Guy broke the kiss to catch his breath. It had gone well. He had entered her in one smooth stroke, no resistance at her sphincter. He enjoyed the tightness he knew would not last through subsequent fuckings. He enjoyed the feel of her smooth skin against his. He enjoyed the way she kissed. That somewhat aggressiveness of a man with the pretended reticence of a woman. He enjoyed the feel of her cock against his belly. Only the false breasts were a distraction, since Guy would have loved to feel his chest against Ellen's natural skin. That would come later, perhaps. Right now it was time to cum.
Guy pulled out until only the head was end, bringing his knees toward Ellen. He shifted her leg so that it was laying on the bed. Ellen brought her legs up, placing her feet flat on the bed. Or as flat as she could still wearing her high heel sandals. She wasn't exactly sure what she should do but sensed that she should line up her asshole with Guy's angle of thrust. Guy began moving in and out of her, slowly at first, then faster as he felt she had adjusted to him.
Adjusted was the right word, for Ellen received neither pain nor pleasure from his thrusting. Just the sensation of the cock in her ass and his movements. She soon found that the most comfortable position was with her thighs pointing straight up, her calves on Guy's back with her ankles crossed at the small of his back. As Guy pounded into her she was reminded of a nail being pounded into a board. Only her own hard dick between their bodies presented a problem, since she still didn't know what to do with it.
When Ellen wrapped her legs around Guy he knew he had truly made her a woman. She had accepted her role and was now responding without prompting or instruction. The only thing remaining was to anoint her asshole with his seed. He began humping her in earnest, stiffening on top of her as he came. He lay there with his cock twitching as he spurted. He kissed her again. She responded by running her fingers through the back of his head with one hand, the other pressed against his side. When he began to go soft he pulled out of her and rolled over onto his back.
'I'm a woman. I'm a woman. I'm a woman' was all Ellen could think. A man had crawled between her legs and taken her. He had pumped and ridden and nailed her until his seed had erupted inside of her. Slowly she sat up and unfastened the garter belt, then removed her shoes and stockings. Guy got up and removed the rubber, wiping himself clean. He placed a second condom on himself and returned to the bed, lying lengthwise.
Naked, she lay down beside him. She looked down her body. Two false breasts rising from her chest, a smooth and hairless abdomen and pubis, a still hard condom sheathed cock sticking up into the air, smooth hairless legs ending in ten painted toenails. Looking at her toes, Ellen's gaze was drawn back to her fingers, interlaced on her stomach, their nails the same color as her toes.
"Come here," Guy growled, placing his hands around her shoulders and pulling her partially on top of him. He kissed her again, taking her cock in his hand. She slumped against him, on her side, her body on top of his, as he jacked her off. It seemed natural now. If she was female as well as a woman, Guy would be finger fucking her. Jacking off is jacking off, only the plumbing is different. Guy was treating her as he would a woman he had just fucked, and Ellen was responding the same. She filled the reservoir of the condom as Guy ran his nails along her perineum.
Guy gripped the base of Ellen's cock, his thumb pressing the underside of her cock as she spurted. He enjoyed the feel of her smooth yet firm body against his as he held her cock. "Thank you, Ms. Sharpe," he said as he kissed her forehead.
Ellen responded by shifting so that she could kiss him on the mouth, her right hand caressing his beard. She looked into his eyes. "Thank you, Guy. I never thought it would be like this."
As soon as she said this Ellen remembered what Brenda had said. Nothing like she had ever imagined. No pain and no shame. She felt she was a woman who had just shed a bothersome virginity, not a man who had just been fucked in the ass by another man. She lay in that man's arms, with that man's hand firmly gripping her cock, having just made her cum. She wanted that man to make her cum again and she wanted to take him into her body and draw his seed again.
She frenched him, then scooted to her side of the bed, legs spread. She began kissing his chest, working her way down his body. He stopped her at his navel. Guy rolled on top of her placing his weight on his forearms and knees again. Ellen reached between them and guided him into her, wrapping her legs around him. She opened her mouth to his tongue as willingly as she opened her legs. She dug her heels into his ass and threw her ass up to him as he pumped her. As he sank into her and came for the second time, Guy knew that he'd womanized her.
As Guy was cumming inside Ellen for the second time, Brenda was cumming inside Jennifer for the second time too. Only she was in Jennifer's cunt, not her ass. The conversations Brenda and Jennifer had on the terrace started out comparing their experiences with Guy. Both had been invited to the ranch after their weekend at THE ESTATE, and both had visited. While Jennifer didn't endure the racism Brenda suffered, she felt as uncomfortable and unwelcomed as her dusky predecessor. Returning to the States, she decided to not only live as a woman, but to become one. Her family was very well off financially, and agreed to the operation as long as they never had to see her again. They also made sure she had a large enough allowance from the family trusts not to bother them.
She did not tell Guy of her decision until after the surgery. He had thought the continuing softening of her skin, the more feminine changes in her body were due to THE ESTATE's treatments, unaware of the hormones she was taking. When she told him, he was not pleased. He was a sissy fucker, and it was as a sissy he wanted her. Jennifer was confused. Guy fucked women--real women. If he fucked her as a sissy, why not fuck her as a woman? He could still fuck her ass, she could still suck his cock, and now she would have a cunt for him as well. Bu t for Guy, it was not the same.
It took several months after the operations--breasts, castration, vagina construction--before Jennifer was able to be about as a woman. She'd wanted Guy to be her first as a woman, but her doctor insisted that he try her new cunt first--to test for post-surgical side effects. Jennifer didn't buy that for a minute, but realized that the doctor was probably the best person to take the new cunt for a road trip. After all, it was his work, he'd done it before, he knew what to expect, and what not to expect. What she didn't expect was that his dick was nine inches by two. She truly felt like a virgin being deflowered as he pushed his way inside.&nbs p; Once in, he couldn't move without hurting her. This is normal, he told her. Just lay back and enjoy the sensation of being filled. Yeah, right. But she did lay back, mainly because she couldn't move. He twitched and stroked it a little, then came after several minutes. He continued to lay on top of her until he became soft enough to pull out. For the first time Jennifer experienced a man's cum seeping from her body. She did not like it.
The doctor looked down at her, proud of his handiwork. The breasts were firm and perky, no scar anyone other than a doctor would notice. The vagina was deep enough to accommodate a man as big as he was--he was quite proud of his size--with the lips slightly protruding. As he watched his seed trail from her body and run down her perineum to the crack of her ass, he imagined what that enlarged asshole would feel like around his cock. Whoever had been fucking her before she got this new pussy must have been a decent size, though not nearly as big as him. As he was planning his next tryst with Jennifer, she was vowing never to let him inside her again, not even his fingers for an examination.
But her biggest disappointment was Guy. The man who loved fucking her as a sissy and who fucked real women, couldn't get it up to fuck a transsexual. Go figure. She'd altered her body permanently for a man who found the new her unappealing. That was several months ago. Since then Jennifer went through a platoon of men, crossdressers, transgendered, whatever. As long as they had a functioning cock. None of the straight men did she tell she had once been a man herself. The crossdressers and transgendered only had to look at her asshole to know i t. It was the she-males who taught her how to fuck as a woman: how and when to throw her pussy up, how to develop muscle tone in her new pussy.
She went from fucking to keep her pussy from closing up--doctor's orders--to fucking because she had a pussy to fucking because she was a pussy to fucking because she enjoyed it. It was only within the last few months that the nerves of her cunt had recuperated enough for her to have feelings there, and the she-males she was fucking made it a point to eat her--she-males named Chantrelle and Adriane. She never obtained a true orgasm, but the feelings she did get were quite satisfactory.
Mrs. Lancaster and her companion did not know of Jennifer's operation at the tea party. They had assumed that Jennifer had a cock between her legs like they did. Brenda knew only because Chantrelle and Adriane had told her so months ago. In spite of being in Maids' Service, they were members and had more rights, privileges and prerogatives than Brenda. When on duty, Brenda was their boss. Otherwise, they were free to enjoy THE ESTATE as members. And they did, including fucking and sucking each other and other queers and queens on staff and off. In last few months of her year of celibacy, both maids had expressed concern about her lack of sex, and suggested several potential partners, including Jennifer Thierry.
So when Jennifer invited Brenda to come by her cabin after she finished with Ellen, Brenda was not surprised. She was noncommittal, to Jennifer's disappointment. She arrived at Jennifer's just as Guy and Ellen reached Ellen's suite, being invited in the same time as Ellen invited Guy. Jennifer took the lead, being both a member and the seductress. She enjoyed the lesbianism of it all--two women kissing, lipsticked lips to lipsticked lips; the removal of skirts and dresses, bras and garter belts, stockings and heels. Only when they finished, Brenda was facing a person with perky breasts and a gash between her legs, and Jennifer faced a cock and balls pointing at that gash.
It took an amazing amount of will power for the two to stay apart while Brenda put a rubber on. It was barely in place before Jennifer glued herself to Brenda, guiding Brenda's cock into place as Jennifer wrapped a leg around Brenda's hips, yoga-style. This was the first time Brenda had fucked a cunt standing up. It had been a long time--years--since Bernard, her male self, had had pussy. Brenda knew that Jennifer's cunt didn't feel the same as a real woman's, but it was close enough, especially to a person who hadn't been inside a real woman for long, long time.
Brenda had also forgotten how a woman's skin feels, having had a man on top of her for a year before becoming celibate. Brenda luxuriated in the softness of Jennifer's skin, unaware of the effects were caused by the hormones Jennifer still had to take. If she had thought about it, Brenda would have realized her own skin was as soft and smooth from the weekly hair removal treatments and skin creams she used, and that it was this feminized skin to feminized skin that added to both their pleasures.
But there was little feminine about the fingers caressing Brenda's balls, except the long fingernails raking the skin behind them. Jennifer combined a woman's touch with a man's firmness in her caresses. With her balls firmly cupped and the area between her balls and her ass being fingered, Brenda came without even thinking how Jennifer learned to milk a cock with her cunt.
Jennifer uncoiled herself from Brenda before Brenda was soft, stepping away from the Black trans. Wordlessly she turned and went to the bedroom, Brenda trailing. Laying on the bed, she spread her legs, pointing to a packet on the nightstand. Brenda's eyes followed Jennifer's finger. This was one ESTATE product she thought she'd never use: dental dams. She took one out and placed it on Jennifer's vagina.
"Lay down between my legs," Jennifer instructed, bringing her heels back to her ass, her knees pointing upward. Brenda complied. "You ever eat pussy?" she asked. Brenda looked up at Jennifer, her face framed by her breasts, and nodded. "Were you good at it?" Brenda shook her head. "Great! Then you won't mind taking instruction, right?" Brenda would have agreed if Jennifer hadn't grabbed her hair and pulled Brenda's face into her crotch. "You don't have to actually eat me, just rub you face in it."
She guided Brenda's head so that her nose was inside Jennifer's cunt, then she rocked her hips so that the lips rode Brenda's cheeks. Brenda's only contribution was to lick Jennifer's perineum whenever possible. It was enough. Jennifer experienced that warm tingling that passed for an orgasm, keeping Brenda between her legs for nearly twenty minutes. Pulling Brenda's head up, Jennifer reached between their legs to find that Brenda was hard again. She guided her inside her, hoping the rubber would survive a second fucking.
Brenda began fucking her in earnest, the body memory of Bernard taking over. Jennifer threw her arms around Brenda and wrapped her legs around her. As they made the beast with two backs, Jennifer wondered why the best fucks she got were from transgendered males. Brenda wondered what it would be like to fuck Jennifer's ass in the missionary position. Three hours later she found out.