T-Girl Sessions - Janet

Story Info
Rob's journey into submission to a T-Girl.
2.3k words
4.47
70k
47
4
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
rick_oh
rick_oh
1,080 Followers

Part 1 – Tantra

Rob had worked hard to get a date with Janet. He thought she was attractive the first time she flashed her bright smile at him at the diner. He kept coming back, and worked up the nerve to ask her out. She didn't say no right away, and mentioned that she had to be selective about who she dated. He persisted, and finally she said yes.

Janet liked Rob, though she figured after the first date he would not ask her out any more. A ride through the countryside, and they ended up at an upscale restaurant in the next town. He encouraged her to select the wine, and she chose a claret.

Janet found that Rob didn't date often, and he was rather quiet. She didn't mind - she was on the dominant side anyway, and found it a worthwhile challenge to draw him out. Half an hour into the meal, she realized that Rob was genuine and wanted to get to know him better. When should I tell him THE important fact, she wondered.

Rob reached across the table and grasped her hand. He looked longingly into her eyes. She smiled at first, then her expression turned somber, something that he immediately noticed.

"Listen to me," she whispered. "I don't want a scene. If you want to call things off right now, I'll understand." She paused a moment.

She leaned forward. It didn't hurt that she showed him some cleavage. She was proud of her firm breasts, and had felt Rob's eyes on them more than once. In a quiet, intimate whisper, she told him, "I'm a pre-op transsexual. Do you know what that is?" She drew back, relieved that she had finally told him.

Rob registered several different expressions in the seconds following Janet's pronouncement. Shock, confusion, a few others, and then poise. "Y-yes, I know what, uhm, what that is." Then he smiled and said, "I thought you were going to say that you're married, or have some fatal disease."

"So, do you want to end this and take me home, or what?" she asked impatiently. She wasn't prepared for what happened next.

He grasped her hand again, and lightly stroked her face. "I do want to take you home - so we can be alone."

An hour later Janet led Rob into her apartment. Once inside, she gave him a hug to break the ice. After telling him a few details of her situation, she had him feel her smooth pale legs. Her rather short skirt, white socks, and sandals drew Rob's attention to her femininity. She saw that he was wrestling with the idea, and wondered how he should react.

She turned his face toward hers, and lightly puckered her lips. Her irresistible eyes, smooth lips, the certainty of her full breasts, drew him to her. A tentative touch of the lips, and they both pressed in for a passionate exchange of kisses.

"Do you want me to show you?" Janet whispered. Rob knew what she meant, and his wide eyes showed his assent.

She led him to her bedroom and told him to undress. "I get to see yours too!" she giggled. She had him get on the bed next to her. "I'm all girl now," she said seriously, "Except for that."

Rob noticed that Janet's cock was rather large.

Janet had Rob feel her breasts and legs, and then her ball sac and semi-firm member. "Feel them as gently as if they were yours," she told him. She chuckled at the delicate way he felt them. While he did that, she reached over and felt his cock and balls, and made approving sounds.

Rob's erection had gotten to a hard, raging state, and Janet's member was firm. She had him lie on top of her, face to face. "It's okay if they touch," she said. It felt strange and exotic to Rob when his cock and balls pressed against Janet's.

"Okay," Janet said after a few moments. She told him to sit up, facing her in a semi cross legged manner. With a bright feminine smile, she moved forward until their midsections touched. She brought their cocks together with one hand and wrapped a flexible cord around them to keep them together.

"Don't be in a hurry," she excitedly told him, and grasped his hands with hers. "We're going to very lightly touch our lips together, with our foreheads touching. When I breathe out, you breathe in, and vise versa."

Rob felt an electric-like zing inside when their lips barely touched. He saw that Janet let her eyes almost close, so he did the same. Long, slow, natural breaths. When he breathed in, he felt energy course to his midsection. When he breathed out, he felt he was giving her part of himself. He had to resist pressing his lips to hers.

The breathing went on for some time, and Rob felt calm energy - energy that was shared between them. After a while he realized that their combined breathing had picked up. With lips lightly touching, their breathing became quick and shallow. He felt a sensation inside him that spread to his erection - the erection that Janet had bound to hers.

When Janet threw her head back a half-whispered "Ahhhhhhhhh!" escaped from her mouth. Rob was convinced he saw flashes of white light when a profound, wrenching orgasm exploded within him. His exclamations mimicked Janet's. A few moments later he looked down and saw that their cocks had both spewed forth an immense amount of semen. The combined juices trickled over their balls.

Janet's slender fingers removed the binding from their cocks, and they both collapsed on the bed. A few tender kisses later, and she asked him if he wanted to come over the following evening. When he said yes, she told him to take a soapsuds enema and two rinsing enemas before coming over. "We're going to fuck," she said.

Part 2 – Penetration

The following afternoon Rob reflected on the previous night's mind-blowing orgasm as he prepared himself for his visit. Janet's blunt phrase from the night before - "We're going to fuck" - sounded at the same time exciting and ominous.

He showed up at Janet's, nervous and excited, with her favorite claret. She appeared happy, and she had fixed a light dinner. Before sitting down to eat, she took off her blouse, and treated Rob to the sight of her naked breasts. They did little talking while they ate - she mostly looked up and giggled when she caught him staring at her bare chest.

"Okay honey," she said, "Let's save the rest of the wine for later. I'm ready for the bedroom."

Rob's insides felt as though they flipped over a few times as he followed Janet to her bed. "Let's get undressed - and I'm going to fuck you first," she announced. They threw off their clothes, and she pointed to the bed. In an authoritative tone, she directed, "Face down on the bed!"

Rob glanced at Janet's erect cock before getting on the bed. Although she was on the petite side, her cock was meaty and at least as large as his.

"That's it - just relax now," she cooed, and massaged Rob's legs and his shoulders. When her hands glided to his bare bottom, she pressed in and kneaded the tension out. When he moaned contentedly, she knew the time was right.

"Spread your legs a little, darling. That's it." She knelt between his spread knees. A glob of petroleum jelly on her cock, and she was ready. She spread Rob's nether cheeks and positioned the tip of her member at his entrance. A firm push, and she partially entered him.

"Uh!" Rob choked out as his response.

"Relax, honey, I'm going in deeper now." Once she was in halfway, she pumped with short strokes until she was totally inside. She lay prone on top of Rob, and placed her smooth legs alongside his.

"Rob - that feels so good," Janet cooed in a tremulous whisper. "Are you okay?"

He felt the fullness of his new girlfriend's cock inside him. "Yes, Janet!"

She pumped slowly for a few moments. Then her thrusting became stronger and quicker.

"I'm going to cum inside you, honey. I'm going to squirt my sperm in your body, and you'll carry it inside you all night!"

"UH! UHH! UHH! UNGH! UH! UHH! UH!" Rob exclaimed in response to Janet's frenzied pumping. He squirmed under her fucking.

"That's right, give me a good ride! I like to ride before I cum - oh - uhh - Oh God, honey!" Janet held on tightly as she let herself spurt uncontrollably inside her new lover.

They both were panting. As she calmed down, she said, "I want to stay inside you as long as I can so you'll get every drop." She gave an occasional pump to eject the last traces of her seed. Eventually Janet's member softened and she pulled out. They cuddled and tasted some claret.

Rob's arousal returned, and he asked Janet if she was ready to reciprocate. She got face down, arched her back, and guided Rob through lubricating and entering her.

Janet's subtle movements served to heighten Rob's arousal, and sooner than he planned to, he erupted inside her. A short exclamation, then he bucked as he ejaculated. Janet's excited mewling made it all the more intense.

He stayed inside Janet as long as he could, and slipped out. Then they slept.

Rob groggily awoke a couple of hours later to the feeling of Janet's cock thrusting in and out inside him. Janet then nudged him face down and panted, "I had to have you again." In the darkness Rob submitted, and felt Janet's cock slither in and out for a long while. When he was sure that his entrance was getting sore, Janet pumped faster. It took a while for her to come to ejaculation, and she gave spirited thrusts as she again ejected her seed inside him.

Rob had conflicting feelings about what just happened. There was no doubt about Janet's femininity - except that she had a cock and a ball sac. Her legs, breasts, and kisses felt good - and so had her spirited fucking, he had to admit. Now, his new lover, Janet, had just finished ejaculating spurts of her seed into him for the second time that night. His back way was still stretched apart from her rather large member, and his insides throbbed. He moaned as she slowly pumped in and out to spill every drop of her ejaculation.

Janet pulled out and got on her back. She pulled Rob on top of her, and in the semi-darkness they enjoyed full body contact. After a while Rob's member, in contact with Janet's, began to firm up. Janet got face down over some firm pillows, and, offering her ass to Rob, implored, "Fuck me!"

He brusquely entered her and draped himself over her. The feeling of her smooth legs against his threatened to send him into ejaculation sooner than he wanted, so he plowed more slowly, sometimes stopping for a moment with his member lodged all the way inside Janet.

"Oh yes, I love the feeling of you inside me!" she exclaimed, and began to move subtly under him.

Rob's breathing picked up and Janet giggled. He knew it was no use trying to hang on longer, and pumped hard. He twisted and writhed as his wrenching orgasm took hold and he strongly spurted.

Part 3 - Surrender and Submission

Janet and Rob spent more and more time together, and she subtly and persistently took a more dominant role in the bedroom. It took some time to get Rob to suck her off and swallow. She had him tell her about the taste and texture of her ample cum. She loved the feel of his mouth on her feet and toes, and frequently had him get her hard with his mouth as foreplay before she took him.

The part she liked best was binding Rob's wrists and ankles to the bed. When he was bound face up, she teased his cock over a long period of time, and when he begged for relief, she enjoyed the sweet pulsing of her own member in his mouth before she either brought him off by hand or let him spend his lust inside her. When she bound him face down, she aggressively fucked him and took delight in the sounds he made as she lustily pumped her cock inside him.

At times she practiced withstanding stimulation before cumming, and gave him an extended fucking, taking frequent long pauses with her stiff member nestled in his receptacle. When she could no longer stand it, she let herself ejaculate, and pumped fast and hard until completely spent.

After taking her pleasure, Janet always allowed Rob to take her, mostly after teasing his cock to a hard and seeping state. Occasionally she took him in her mouth, but most often enjoyed the feeling of his throbbing erection inside her, and often brought him off quickly with her wiggling under him. She learned that when she rapidly clenched and relaxed her nether globes during sex Rob could never endure the stimulation long before erupting.

Janet told Rob that she wanted him to shave his body from the waist down, that it would feel good when they were in bed. It was an immense turn-on for Rob as well, kissing her passionately while their naked legs touched.

As they were getting ready to take pleasure one night, Janet fed Rob's fantasies by mentioning that she wanted to include another T-girl friend of hers in their bedroom play. "We're both going to fuck you good, and you can fuck both of us. You have to work on being able to fuck without cumming so soon. Get the lube - you can start practicing now."

She gave an aroused sigh as Rob entered her.

rick_oh
rick_oh
1,080 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
4 Comments
BobluvsBobluvsover 11 years ago
Next in the series

Great story really enjoyed it. Can't wait for the next one. when will that be. It seems like its been a while since you wrote this one.

NormCastleNormCastleabout 13 years ago
I want

I WANT TO BE ROB

!

the_apocalypsethe_apocalypseover 13 years ago
Please

There just has to be a sequel, that was excellent

yorkie54yorkie54over 13 years ago
MORE

That was hot. I hope you don't leave it there

Share this Story

Similar Stories

Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
The Backdoor Sex in a club's restroom with a dominant t-girl.in Transgender & Crossdressers
Shemale Bar Straight guy goes into a shemale bar and is forever changed.in Transgender & Crossdressers
The Big Mature Shemale Next Door Little guy is fed cum and seduced.in Transgender & Crossdressers
New Neighbors Two dominant tgirls move into the building.in Transgender & Crossdressers
More Stories