Jeff and Chelsea - Cover

Jeff and Chelsea

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

Chapter 8

Erotica Sex Story: Chapter 8 - 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 woke him and he saw Chelsea facing him. “Jeff...”

“By the look on your face and the tone of your voice I can tell this is something deep.”

“About last night...”

“I thought we discussed last night ... last night.”

“That was about us. This is about me...” She touched his cheek. “Jeff ... I always kind of liked thinking I couldn’t ejaculate. Somehow it made me feel more ... feminine. I always thought a female orgasm was internal and that’s what I was experiencing. What I had last night was a man’s orgasm.”

‘“No. What you had was a Chelsea’s orgasm,” he responded.

“What I had is making me re-consider the surgery.”

“Re-assignment surgery?”

“I’ve been reading a blog written by another trans-woman who’s post-op. She had the procedure about a year and a half ago and she wrote about the experience. She listed all the negatives -- the cost, that she had to go to Thailand to have it done. She went to a clinic that specializes in the procedure and is located next to a hotel that they use as a recovery and rehab center. She said that for the first month she was bed-ridden. The pain was so intense she became addicted to morphine and then had to recover from that. It was three months before she could go home, six before she could go back to work and a year before she was fully healed. She had to use these appliances called vaginal dilators.”

“Vaginal dilators?”

“They’re like large plastic thimbles she inserted to keep her new vagina from irreversibly collapsing while the tissues healed. She still wears one today, although not twenty-four seven. Then there’s the hygiene issues -- an artificial pussy lacks the normal cleansing mechanisms of a natural one so she needs to douche regularly.”

“Do you really want to go through all that?” he asked.

“Would you really be satisfied with butt-fucking the rest of your life?”

“I told you I prefer it.”

“Maybe it wouldn’t be my preference -- IF I had a choice. That same T-woman listed the positives. First, now she has an anatomy that matches her identity. Second, she is fully orgasmic. She wrote how after eighteen months she worked up the nerve to try her vibrator and she had an orgasm. She also wrote that, to her surprise, she experienced a pearlescent fluid flowing from her.”

“That makes sense,” he observed. “They probably didn’t disturb her prostate.”

“She wrote that what she experienced wasn’t a male orgasm or a female one but a trans-sexual one. That’s the kind I would want. If I were posr-op and we were making love and I emitted pearlescent fluid ... Would that be a turn-off?”

“Not at all. In fact, it sounds sexy as Hell. You do know, if you endured all that there’s a small but real chance you’ll have no orgasms at all.”

“I know that. They are making big strides in the procedure.”

“The last time we discussed surgery I told you that, if you’re considering this, do it for you, not for me. I love you exactly how you are. However, you have given me compelling reasons for doing it for you.”

“That decision is years if not decades away,” she replied. “The blog author was in her forties.”

“Forty is the new thirty,” he replied. “If this is your decision you should do it sooner rather than later. If you do it, you have my one hundred percent support. I will hold your hand as you go under and my face will be the first you see when you wake up. I will give you whatever support you need to make your convalescence as easy as possible. And I will not stop loving you, and I won’t love you any differently.”

She wiped away some tears. “Thank you.” She kissed his lips.

“Now, I have to get ready to meet with my advisor.”

“Yeah, me, too.”

“The dining halls should be open. Let’s plan dinner and then head down to register.”


Jeff made the hike across campus to his dorm and unlocked the door. Ted was sitting at his desk. “When did you get in?” Jeff asked.

“Last night,” Ted replied. “When did you get in?”

“Yesterday afternoon. I spent last night with Chelsea.”

“Figures ... You know on the bus from the airport I sat with a girl ... a senior. Her name is Morgan Turlock and she was in Wheeler House last year. I told her we knew someone in Wheeler -- Chelsea Lane.”

“Does Morgan know Chelsea?”

“She remembers her ... strange girl, she said ... shy, nerdy ... always kept to herself. Never went out on dates, never really mixed with the other girls. She stayed in her room unless she was in class or at meals. Even then, she always sat by herself and rebuffed any of the other girls’ attempts to be friendly with her. Morgan says there was some ... talk.”

“Talk?”

“Yeah ... A freshman in a Wheeler single when it’s normally reserved for upperclassmen? They couldn’t figure that out. And then there was a rumor going around that Chelsea is ... you know...”

“I know what?”

“A shemale ... TG ... ladyboy. I told Morgan that my roommate was dating her. She said she couldn’t believe it. I told her, believe it -- they’re going steady. He spends nearly every weekend over there.”

“What did she say to that?”

“She said whatever makes your toes curl. Next time you see Chelsea, ask her if she remembers Morgan Turlock.”

“I’ll do that ... maybe...” Jeff picked up some envelopes on his desk. “What’s this?”

“Your mail. I picked it up for you. It’s all university shit.”

“Anything important?”

“The usual. Housing form for next year is in there. You wanna go in together again?”

“Oh ... Well ... Actually...”

“Actually what?”

“Actually, Chelsea and I are thinking about sharing an apartment off campus next year. Two can live as cheaply as one.”

“Are you shittin’ me? You two really want to live off campus?”

“I think we do.”

“If that’s what you want to do, you’d better find a place soon. The good ones go fast.’’

“I know. I’m gonna be on it this week.”

“That sucks, man. I’ll need to break in a new roommate and I just got you trained.”

“Sucks for you, maybe. You’re wrong about one thing. Chelsea and I are not going steady.”

“No? What do you call it?”

“We call it being engaged.”

“Holy shit.”

“No guff,” Jeff replied. “She’s wearing my ring and everything. I wonder what Morgan Turlock would think of that.”

“Yeah, I wonder ... Holy cow ... Another one bites the dust. Congratulations, man.”

“Thanks. Now, what time is registration?”

“Sophomores between six and seven,” Ted replied.

“You still have your car here?”

“Yeah.”

“You driving down?” Jeff asked.

“I was going to hitch a ride with Josh and the guys but there’s a change of plans. I guess I’m driving. You want to ride along?”

“I thought you’d never ask,” Jeff replied. “Chelsea, too?”

“Sure, why not? I’d like to meet your bride-to-be.”

“We’re meeting at the quad cafeteria for dinner,” Jeff replied. “Why don’t you join us and then we can head downtown.”

“Sounds like a plan.”


Jeff stood with his roomie in the lobby of the Quad Core. “You said five?” Ted asked.

“Yeah, she’s usually on time. Here she comes.”

Chelsea approached them and, spotting Ted, stopped short. “Chelsea,” Jeff said, “this is my roommate Ted. Ted, Chelsea Lane, my fiancee.”

Ted extended his hand. “Pleased to meet you.”

Chelsea grasped his hand lightly. “Same here.”

“Ted has his car,” Jeff added. “I thought we could have dinner and ride with him downtown -- save us a half-hour hike in the cold there and back.”

“Well, thank you,” she said to Ted.

“Shall we go up?” Jeff asked and the three climbed the stairs to the cafeteria. The three went through the line and checkout, presenting their meal plan cards. Jeff spotted an empty four-top table and headed toward it with Ted and Chelsea following.

Ted sat across from Chelsea and Jeff between them. “Jeff tells me you’re engaged,” Ted said. “How did that come about?”

“We spent some time together during the break,” Jeff replied. “We had a long talk, we knew where we’re headed and decided to make it official.”

“Do you have a ring?”

Chelsea placed her left hand flat on the table. “It was Jeff’s grandmother’s,” Chelsea said.

“An heirloom,” Ted replied.

“Yes, they’re letting me wear it.”

“They gave it to you,” Jeff added.

“Right. I mis-spoke.”

“Have you set a date?” Ted asked.

“No,” Jeff replied. “It won’t be before we graduate, though.”

“Jeff said you two are looking at off-campus housing for next year.”

“Yeah,” Jeff said, “I have a lead on a couple of places.”

“You know,” Ted added, “that if you moved up your wedding plans you might be able to get into married student housing. It’s not as cheap as off-campus but a lot nicer.”

“That’s an idea,” Jeff replied. “Something to think about. I’m surprised it’s not domestic-partner housing the way things are going these days.”

“I think they still require a marriage license to qualify,” Ted said. “I need a soda refill. Can I get you anything?”

“Maybe top mine up.” Jeff handed him his glass. “Diet Coke.”

“Chelsea?”

“I’m good.”

Ted headed toward the soda machine. “Why didn’t you warn me Ted was joining us?” she asked sotto voce.

“It was a spur-of-the-moment thing. He has his car and offered us a ride. You remember we borrowed it for that drive to Bear Mountain.”

“I remember. I hope he cleaned out those burger wrappers.”

“I hope he cleaned out all the condom wrappers,” Jeff added.

“Ewww!”

“He probably did. He drove it home for the break and I’m sure he wouldn’t want his folks to see those.”

“Jeff, you know I hate surprises like this. I’m getting a mild form of the anxiety I had when I first met your folks.”

“Hyperventilating? Palpitations?”

“No. The stakes were higher then. Still, you could’ve texted me so I wouldn’t have been blind-sided.”

“I’m sorry. Yes, I should have texted you. But, you need to work on this, Chelsea. Everything worked out okay with my folks and it’ll work out with Ted.”

“Yeah, you’re right. I need to figure out how to de-sensitize myself when it comes to interacting with strangers.”

Ted returned and set Jeff’s glass before him. He turned to Chelsea. “Jeff tells me you’re pre-med.”

“That’s right.”

“Do you have a specialty you’re interested in?”

“I might not go to med school. It’s awfully expensive. I might go for a PhD in a related field and work in the healthcare industry. If I can be a research assistant it’ll save on tuition. I haven’t decided yet.”

“I’m pre-law,” Ted replied. “Law school is awfully expensive, too. My dad’s a lawyer ... has his own practice. I think he wants me to join ... become a partner, maybe take it over some day.”

“Sounds like you have everything planned,” she replied.

“Or, planned out for me.” He turned to Jeff. “What are your plans?”

“I dunno, probably go for a PhD and go into industry. Maybe organic or bio chem and work in pharma. I haven’t really found my niche.”

“All he knows for sure is, it’s not thermodynamics,” Chelsea added.

“That’s right,” Ted remarked. “You were cramming like crazy for that final when I left for break. How did that work out?”

“I’m still here. I pulled a 2.9 final for the course which made my overall 3.76. So not only did I keep my scholarship I also made Dean’s List.”

Ted consulted his watch. “Shall we head downtown? It’s a bit early but maybe we can be at the head of the line.”

“I’ll take your trays.” Jeff deposited their trays and tossed their detritus, pulled on his jacket and followed Ted to the parking lot.

Ted unlocked his ten-year-old Kia four-door. Jeff and Chelsea sat in the back. After a short drive Ted pulled into a student parking lot. “Place is full,” Jeff remarked.

“Not entirely full,” Ted replied and pulled into an empty stall near the building’s door.

“Isn’t this handicap parking?” Jeff asked.

“Got it covered.” Ted removed a handicap placard from above the visor and hung it from the rear-view mirror.

“Where did you get that?”

“Ordered it on-line.”

“You know they crack down on that,” Jeff admonished.

“Out-of-state plate, out-of-state card. I doubt the local cops would bother tracking it down.”

“I’d be careful. If you got caught you could be in trouble.”

“It’s only for emergencies.”

They headed inside the hall and joined a short line in the lobby. The inside doors were closed and locked. Ted glanced at his watch. “We have a short wait.’

Jeff held Chelsea’s hand and she gave him a slight smile. Shortly the inner doors swung open. Card tables were set up alphabetically. Jeff headed toward the table serving A-F, showed his student ID and picked up his registration packet.

He joined Chelsea near the door. Ted joined them shortly. “Let’s scram out of here,” he said.

Ted stopped the car near the Wheeler door. “I’ll be getting out here,” Jeff said, “so we can compare schedules. I’ll catch up later.”

“Thanks for the ride,” Chelsea added. She closed the car door and Ted sped off.

Holding hands Jeff and Chelsea headed toward her room. “What do you think of Ted?” he asked.

“I think he’s a player ... skirting the rules with that phony handicap card. I didn’t like that.”

“Ted’s the sort of guy who never breaks any rules HE thinks are important. But he’s basically a good guy.” Jett opened his packet and took out his class schedule. “Let’s see ... Two eight o’clock labs Tuesdays and Thursdays ... which is tomorrow. Crap!”

“I only have nine o’clocks on Tuesdays and Thursdays. Otherwise my classes are late mornings and early afternoons.”

“Same here ... Do you know what that means?” He counted on his fingers. “Thursday, Friday, Saturday, Sunday,,, Four nights a week we can be together.”

“And, Tuesdays ... depending on workload.” They embraced and kissed. “It’s going to be a good semester.”

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