Jeff and Chelsea - Cover

Jeff and Chelsea

Copyright (C) 2023 by the author. All rights reserved.

Chapter 3

Erotica Sex Story: Chapter 3 - The story of Chelsea, a college sophomore who is trans-sexual and her boyfriend/fiance Jeff. Jeff meets her as shy and introverted. She initially rebuffs his advances but relents when she discovers shared interests. They fall in love and begin a sexual relationship. The growth of their love parallels the growth of Chelsea's self-esteem. She outs herself publicly with bittersweet consequences.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Romantic   Shemale   TransGender   Anal Sex   First  

Morning light roused Jeff. He saw Chelsea lying on her side and regarding him. “Morning,” he said.

“Morning.”

“Been awake for long?”

She shrugged. “Not really...” She regarded him for a long moment. “So...”

“So what?”

“Any regrets?”

Jeff shook his head. “No. None.”

“You’re sure?”

“Positive. Like I said -- you’re a girl with a different kind of clit, that’s all. You have any regrets?”

“Oh, Jeff ... You can’t imagine what this has done for my self-esteem. To actually feel wanted ... to actually feel desired, physically. I never thought I’d feel that.”

“I do want you and I do desire you.”

“I know. I can feel it. I FEEL it, Jeff.” She leaned toward him and they kissed. “There’s something else I can feel.”

“What’s that?”

“The trust. For each of us to lie, naked and spread-eagle in all our vulnerabilities...”

“I believe good sex is giving and trust,” he replied. “Each partner gives one hundred percent and trusts the other to do the same.”

“Really well expressed, Jeff.”

“Last night was pretty special for me, too,” he replied. “I have feelings for you, Chelsea, that I’ve never felt before.”

“It’s not because I’m trans, is it? Jeff -- if it turns out that I’m just another scalp ... another trophy ... That would destroy me.”

He regarded her, slack-jawed for a long moment. “That would be cruel beyond cruelty. I’m not that sort of guy. You just got done saying you trusted me.”

“Oh, I trust you. I’m just having trouble believing it.” She made a little snort. “I just had a mental image of that scene in ‘Fifth Element’ when the Chris Tucker character is coming on to the flight attendant. He says, ‘I swear. I’ve never felt like this before ... with a human.’”

“Do you really think I’m like that?” he asked.

“No. It’s a nagging fear. It’s my female spaghetti-mind lurching from A to B to C. I still don’t understand why you want me.”

“It’s because I have such an intellectual connection with you, Chelsea. I’ve never had that before ... with anyone, human or otherwise.” He touched her jaw to turn her face so he could gaze into her eyes. “With anyone, Chelsea. The more we worked together on that project, the more I wanted you. I find your intelligence and intellect sexier than your body ... and you have one helluva sexy body. Don’t forget. I wanted you even before I knew you were trans. I don’t want you because you’re trans. I want you because you’re you and being trans is just one aspect of you.”

“You always say the right thing. I’m sorry I said what I said and I wish I could take it all back. I believe you, Jeff -- and I trust you.”

“It was special for me because I felt we were communicating, physically. I hadn’t felt that sort of a connection with anyone else, either.”

“I felt that, too.” She traced his lips with her finger. “No. I don’t have any regrets.” Jeff coaxed her against him and she smoothed her fingers across his chest. “I have doubts, though.”

“What sort?”

“That I can satisfy you ... long term ... physically. You seem more adventuresome than I am. You were doing oral on me. I still need to work up to performing it on you, Jeff. I’m not ready for that, yet. Guys do like blowjobs, don’t they?”

“As far as this guy goes ... not so much. Certainly not more than real sex.”

“By real, you mean...”

“Going all the way,” he replied.

“Penetrative sex is the ultimate,” she replied.

“It’s why it’s called going all the way. I’d love to go all the way with you, Chelsea. Isn’t it something you’d like to experience, too?”

“You know me pretty well. I think you know the answer to that question.”

“You know what it means, though.”

Chelsea drew back the corners of her mouth and grimaced. “Yes. It means anal sex.”

“Is it a problem for you?”

She sighed. “I’ve been hoping ... and, dreading ... that we’d broach this topic. You’re right. It isn’t real sex without it.”

“Chelsea, if this is too soon for you ... If we’re going too fast ... it’s okay if we don’t...”

“Jeff ... You said you didn’t know how you’d respond until you tried it. I’m the same way. I need to know if this is something I can do. It’s something I want and something I’d do in a heartbeat ... except...”

“Except for what?”

“Except for the ick factor. I don’t know if I can get past it. It’s how I grew up, Jeff. It was drummed into me ... how dirty that part of my body is.”

“The way I see it -- buttholes are like opinions. Everybody has one. Sure, it’s icky ... but it’s part of life. We can deal with the ick factor. We can clean you out, first.”

“What do you mean?”

“It’s called an anal douche. It’s along the lines of a vaginal douche...”

“Which is something I know nothing about,” she interjected.

“ ... you introduce a small amount of water into the rectum to rinse it out.”

“Do you mean an enema? When I was in high school I came down with a bad ear infection. I took an antibiotic that made me constipated and the doctor recommended enemas. I did not have a good experience. They gave me cramps and made my belly hurt. I was so glad to be off the antibiotics.”

“This is different. You probably used the little squeeze bottles from the drugstore.”

“Yeah...”

“Those are filled with a strong laxative solution to force you to have a bowel movement. Normally your colon does a good job of keeping your rectum empty until it’s time to go potty. We’ll use plain water to rinse out any residue.”

“How do you know about this?” she asked.

“I had a girlfriend when I was in high school. She was from a conservative, religious family and she believed she should save her virginity for marriage. She also was so hot and horny you couldn’t spit on her.”

“A technical virgin,” she remarked.

“I’ve always felt that virginity is more a state of mind than one of body. When it came to state of mind ... she definitely was no virgin. She wanted to fuck but the front door was out of the question. As for back-door action she was turned off by the ick factor as well. She suggested anal douching.”

“She thought doing anal somehow preserved her virginity?”

“It preserved her state of body ... and, her conscience.”

“And,” Chelsea added, “no risk of pregnancy.”

“Not entirely. All it takes is a stray sperm finding its way.”

“Well, the risk is zero in my case,” she retorted. “So -- what did you do?”

“I kept my briefs on until the last moment.”

Chelsea rolled her eyes. “No -- what did you do to prep for anal sex?”

“We used an anal douche and never had a problem.” He looked into Chelsea’s blue eyes. “Are you game?”

“For you I am,” she replied. “You took a big chance with me. Now it’s my turn to take a big chance with you.”

“Today is Saturday. Have anything planned for this evening?”

She shook her head. “No. Nothing. Nothing that can’t be put off ‘til tomorrow, that is.”

“I can take a walk to the drugstore and get what we need. Then, we can have dinner together and come back here.” He looked at the clock on her stand. “Eight-thirty. Want to get some breakfast?”

“Not a breakfast person, really.”

“I’ll want to shower and change.”

“You can shower here.”

“Then I’ll have to put on the same clothes. I’ll go to my place and shower. We’ll get together this afternoon. It would give us a chance to run some errands or whatever.”

“Mmm ... I’d like that.”

He swung his feet to the floor, stood and stretched. He began picking up his clothes. Chelsea approached him. “Jeff...”

They faced each other, nude. “You do have one sexy body,” he said.

“Jeff ... I ... I...” She bit her lip.

“What’s the matter? That pulse point in your neck is pounding again.”

She drew in a breath. “Jeff, I love you,” she blurted.

“I know. I love you, too.” They embraced and he ran his hand along the small of her back and buttocks.

“I was so scared to say it ... so scared to ruin what we have.”

“How could that ruin it? It’s not anything either of us didn’t know ... down deep that is.”

“Not even that deep.”

Jeff pulled on his jeans and shirt. “See you for dinner.”


Jeff sat at his desk, working on an assignment. His roommate stepped in.

“So, there you are. Where were you all night?”

“I didn’t know it was your night to watch me,” Jeff replied.

“Well, your mom called around nine-thirty.”

He looked up. “What did she say?”

“She said she tried calling your cell but no answer.”

“I had it in airplane mode. What did you tell her?”

“I told her you were out.”

“Hmm. Well, if you must know I was with Chelsea.”

“Welly, welly, welly ... How did that go?”

“You know, it’s pretty crass to ask a guy that ... and even more crass for a guy to answer.”

“Jeez ... sorry.”

“You can surmise things went well enough for me to stay the night.”

“Yeah ... right...”

“ ... And, I have a date with her again tonight.”

“So if your mom calls...”

“I’ll call her first. You shouldn’t need to field any calls for me.”

“If I do -- is it okay to call your cell?”

“It’ll be in airplane mode so we won’t be disturbed.” He saved his work and powered down his laptop. “I have an errand to run. Don’t wait up for me, Ted.”

“Don’t worry -- I never do.”


Jeff stepped into the Wheeler House lobby carrying a soft duffel. He took out his cell and called up Chelsea’s number.

I’m downstairs, he texted.

Be right there, came the reply.

He paced by the door leading to the residential floors. It opened and she approached him. They embraced and kissed. Jeff stepped back and scanned her up and down. She was wearing a halter-style top, denim shorts and sandals.

“You look terrific,” he remarked.

“Thanks...”

He held up the duffel. “Maybe I can drop this in your room.”

“Sure.”

He followed her through the door and to her floor. She opened her room and he set the duffel inside. “This is what we’ll need ... and a change of clothes. Ready for dinner?”

“I’m kinda nervous,” she replied. “I don’t have much appetite.”

“If we don’t eat now we’ll be hungry later.”

“Right.”

Holding hands they made the walk to the quad cafeteria. Each picked up a tray and went through the line. Jeff selected a burger and fries while Chelsea made a peanut butter-and-jelly sandwich. “That’s all you’re having?” he remarked.

“I told you -- I don’t have much of an appetite. I’ve been thinking about this evening all day,” she said. “It’s a wonder I got anything done.”

“I’ve been thinking about it, too.” He finished his soda. “I’ll take your tray.”

Holding hands again they headed back to her dorm. Chelsea closed and bolted her door. Jeff took his cell from his pocket and switched it to airplane mode. He picked up his duffel, unzipped it and removed a plastic bag from the corner drugstore.

Chelsea approached him. “Should I change into something?” she asked.

“We’ll need something with access to your bottom.”

“Right...”

Chelsea opened a dresser drawer and began sorting through it while Jeff carried the bag into her en suite bathroom. There he ran water in her sink to take off the chill.

“Will this do?” Chelsea had on a slip-style nightgown, the hem of which cut across the upper third of her thighs. It was of light blue cotton. The bodice clung to her compact breasts and Jeff could discern the outlines of her areolas through the thin fabric.

“That will do just fine. You look sensational in it, Chelsea. It matches your eyes, and it shows off your pretty legs. You wear that to bed?”

“Sometimes.” Jeff removed from the plastic bag a drug-store squeeze-bottle enema. “My God!” Chelsea exclaimed. “That looks just like what I had to use in high school.”

“It probably is but we’re going to re-purpose it...” Jeff opened the box and removed its contents. Unscrewing the cap he dumped the solution into her sink. He rinsed out the squeeze-bottle and filled it from the tap. After replacing the cap he handed it to her. “Nothing but harmless tap water.”

Chelsea eyed it suspiciously. “I don’t know...”

“The things only cost a couple bucks so we can regard it as disposable.”

“I’m getting flashbacks. My mom administered it. She had me lie on my side. She inserted it and squeezed it into me. I still remember the sensation -- a cool squirt deep inside. Then I felt a burning sensation and discomfort in my belly. She told me I had to lie like that until the enema gave me a strong urge to go. It must have been five minutes but it felt like fifty. I had awful cramps. I had to endure that four times ... until I was done with the antibiotics.”

“These contain a strong phosphate salt solution that works by irritating the lining of the colon, and they also draw fluid from your body by osmosis to soften the stool.”

“How do you know so much about these things?” she asked.

“I’ve had my own experience with them, the details we can discuss later. Now what’s in it is plain tap water -- no harsh salt solution. I guarantee no cramping.” He removed a tube of personal lubricating gel from the bag and set it near the sink. “The tip is pre-lubricated but with repeated insertions you might need to add more.”

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