Jeff and Chelsea
Copyright (C) 2023 by the author. All rights reserved.
Chapter 4
Erotica Sex Story: Chapter 4 - 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 opened his eyes and regarded Chelsea. She lay on her side facing him. “Morning,” he said.
“Morning.”
“Been awake long?”
“A while. I’ve been thinking.”
“About...”
“About us.”
“Starting to have regrets?”
“It’s complicated. This weekend has been life-changing for me, Jeff. I never imagined I could have this. I never imagined I could receive a man inside me and wake up in his arms. It wouldn’t have happened with anyone else, Jeff. You’ve been so gentle and patient ... understanding and open-minded.”
“And, persistent?”
“Oh, that for sure. I told you being a trans-woman is about self-identification...”
“I remember. Yesterday after I went back to my room I did some on-line reading about trans people. I understand what you’re saying -- as much as I can without living it. I didn’t realize that some women are as hostile to you as men. I mean -- I can understand some homophobic dudebro regarding a sexy trans-woman as a threat to his hetero-manhood. But for other women?”
“Oh, yeah,” she replied. “Some of the most virulent hate mail Quinn gets comes from women ... feminists, in fact. If Quinn goes on a feminist rant ... she gets some real vicious replies from other feminists ... who think she has no business being a feminist. They accuse her ... me of appropriation.”
His eyes filled. “I don’t understand it. I don’t understand why we can’t just accept each other for who we are.”
“Oh, Jeff ... The way you accept me? You are sweet...” She stroked his cheek. “I told you I was comfortable with who I am. I was ... until now.”
“What do you mean?”
“I want to investigate re-assignment surgery.”
“You’d put yourself through that?”
“I’ll do anything to please you, Jeff.” She caressed his face. “Wouldn’t you really rather have a girlfriend with a pussy instead of a dick?”
“I want you. I read about reassignment surgery. The description of the procedure is the most cringe-inducing thing I’ve read. If you undergo that -- there’s a good chance you’d lose your ability to feel orgasm.”
“I know.”
“It’s an awful price to pay. Making you come is a big part of my enjoyment, Chelsea. I know you giving me one is a big part of your enjoyment. If you think you want reassignment surgery -- do it for you, not for me. I’m happy with you just the way you are.”
Her eyes began to fill. “You tell me that and I have to believe you. I don’t understand why.”
“Chelsea, if we’re going to be in a relationship we need to be brutally open and honest with each other. I was more nervous going into Friday night than I let on. I told you that the idea of gay sex -- two hairy, smelly, bearded men going at it-- turns me off. Don’t get me wrong. I believe what two consenting adults do in private is no one’s business but theirs. I had to put those homophobic thoughts aside and when the moment came to handle your...”
“My dick? It’s okay to use the word. It won’t offend me. I’ve had it my whole life, after all.”
“When I started touching it and stroking it I could feel it respond. That with your expression and body language is how I knew I was arousing you ... and that was powerfully arousing to me. Because I understood ... I knew what you were experiencing because it’s what I experience. It’s something we have in common. Feeling your ... dick get hard and throb from my touch was so sexy to me I almost came then and there. I feel a connection with you I’ve never experienced with any girl. The fact you have that other kind of clit doesn’t diminish your beauty, your sexiness, your femininity or your identity as a woman one iota in my eyes.” He kissed tears from her cheeks. “Are you okay?”
She nodded. “Yeah, I’m okay. That was beautiful, Jeff. Tell me -- did Friday night change your mind about gay sex?”
“No, because I don’t think I could love a man the way I love you. For me, love has to be there first. I could not perform with a stranger, even if she were the most beautiful sex-pot on the planet, if I didn’t love her first. You’re the one I love, Chells. Is it okay for me to call you Chells?”
“It is. I like it. It sounds cute and loving.”
“So, have we put to rest how I could love you?”
“Yes, we have pounded the last nail into that coffin.”
“Good.”
“But, about the surgery ... I’m thinking it just might be worth the risk. Wouldn’t you like us to be able to make love, face-to-face, like a normal couple?”
“But, Chells...”
“I mean, last night was wonderful. I loved feeling you fill me. I loved feeling your climax when you were inside me ... feeling you get bigger and harder and start throbbing as you came...”
“Chelsea...”
“Nonetheless, there was something about it that was a bit...” She held up her thumb and forefinger, almost touching. “ ... just a bit ... degrading. I’ve always thought one thing that elevates us above animals is that we make love, face-to-face ... as equals. There was a ... a domination aspect that I didn’t really care for...”
Jeff let out a shrill whistle and held his palm against his fingers in the Time Out gesture. “Chells ... I agree with you one hundred percent. I want to make love to you, face-to-face -- as equals. What makes you think we can’t?”
“I ... I just thought...”
“You assumed back door means rear entry. I picked doggy style last night because I thought it would be easier for you for the first time. Really, there are few cis-hetero positions that can’t be adapted to the back door. Hannah and I used to do anal missionary all the time. It was our favorite.”
“Really?”
“Really. All you need to do is to aim a little lower.”
She giggled. “Hearing you say that ... makes me want to try it.”
“Then, let’s try it.”
“Now?” she asked.
“Why not? It’s early Sunday morning. I don’t have anyplace to go. Do you?”
“No.”
“Church?”
She smiled and shook her head. “I lost my religion when I was about ten ... when my folks started letting me live as a female. Our church expelled us ... our whole family. The pastor said it was sinful what we were doing and if we wanted to remain members we had to stand up in front of the congregation, admit our sins, repent and change our ways.”
Jeff shook his head. “I’ve never been religious and the more I see of this sort of thing ... It reminds me of what Gandhi said.”
“What was that?”
“He was asked his opinion of Christianity. He said he liked Christ but didn’t care for Christians. The ones he had met, he said, weren’t very much like Christ.”
“My folks said, screw it and we never looked back. We stopped going and we stopped caring. It was like getting fifty-two hours of your life back every year.”
“So, are you game?” he asked.
“If you are.”
“Oh, I sure am. If you don’t mind, I’ll go whiz. Do you need to?”
“I was up earlier.”
“I’ll be right back.”
Jeff stepped from Chelsea’s bathroom. “Loo’s ready for the next customer,” he said.
“I’m good,” she replied, “unless you think I need...”
“A rectal rinse? You should be okay from last night.” Jeff joined her in her bed. He sat up against her headboard and she sat between his legs and rested against him. “I love how you’re holding me,” she said. “I love it when you kiss my neck.”
Jeff cupped her breasts in his palms. “Your breasts are so gorgeous,” he said as he ran his thumbs across her nipples. “These perky little nipples are getting so hard.”
“Feels good. You’re making something else hard.”
“Ready to move down?” he asked as he nuzzled and kissed the base of her neck.
“Not quite. I love how all this feels ... I want to savor.”
Jeff could feel her heart through her breast. Its beating grew stronger and faster as her arousal built. Chelsea placed her hands on his thighs and squeezed them.
He turned his attention to her smooth and shapely legs, caressing her thighs. He moved his hand up and across her firming shaft, teasing her glans with the pads of his fingers. “I love how you touch me,” she said. “It feels as if you’re worshiping my body.”
He continued gently stroking her she-cock, pressing it into her pubic hair and against her lower abdomen. “Feels really good,” she said softly. “Just what I wanted.”
He could feel her erection stiffening and he began pinching her nipples alternating left and right. “Your nipples feel like pebbles,” he remarked.
“Feels so good ... Don’t stop ... I’m gonna come.”
He increased his stroking of the underside of her glans. “Then come ... come to Jeff...” She began panting and the muscles in her thighs tensed. “That’s the girl. Come, baby, come...”
Chelsea grasped his thighs, let out a groan and then gasped. Jeff felt her shaft throbbing. Then she leaned against him, her body limp, as her breathing slowed. “Your face got pink,” he remarked.
“Good one,” she said. “Really good.”
“Are you ready to try missionary?”
“Tell me what I need to do.”
“Lie flat on your back and draw up your legs as far as you can. If you need to, you can hold them behind your knees and pull them back.”
Chelsea lifted her thighs, grasped her legs and drew them back. “Now, grab your butt cheeks and spread them.”
She complied. “I never thought I’d expose myself like this to a man,” she remarked. “I’m just glad I don’t need an ob-gyn.”
“Lucky you. Chelsea -- do you trust me?”
“Absolutely or I wouldn’t be doing this.”
Jeff picked up the lube and squeezed some onto his finger. “Like last time I’m going to lube you and dilate you a bit...” He worked first one and then two fingers into her anus, rotating his wrist to relax and open her sphincter. Then he smeared his stiff member with the slippery gel. Holding his shaft he aimed at her opening and pressed against her.
Her anus admitted him without difficulty and he eased himself in. He watched her pinkish-brown opening expand and his shaft disappear into her. Once he was most of the way inside he lay atop her. Gently he rocked his hips to drive himself in the rest of the way. Chelsea’s eyes widened and her mouth gaped. “Are you all right? Am I hurting you?”
She shook her head. “No ... Feels really good, Jeff. Really good.”
“Feels really good to me, too.”
“Can we just lie here like this for a while so we can savor the intimacy?”
“Certainly ... You can put your legs down or whatever.” She crossed her ankles atop the small of his back. “I like feeling your smooth legs against me.” He cradled her head in his hands and kissed her lips. “You are so pretty.”
Chelsea bit her lip and shook her head. “Uhn-uhn,” she said.
“But you are. I love your blue eyes, cute nose and freckles ... I love your apple cheeks when you smile. I had some kind of a crush on you last year when I saw you around campus...” Her eyes began to fill. “Now what’s wrong?”
“Oh, Jeff...” She sniffled. “It’s as if ... as if I found something that I never knew I was missing. I feel whole as a woman and I never realized I was incomplete. I need this without ever knowing I needed it.”
“It’s powerful stuff, isn’t it?”
“Yes, it is.”
He kissed tears from her face. “I found something I never knew I was missing, too,” he said.
“What?”
“A woman whose mind is as beautiful, as attractive and as sexy as her body.”
“Oh. Jeff...” She smiled. “I’m okay now. I was just overwhelmed for a moment. Jeff -- I have never felt intimacy like this ... ever ... with anyone. It’s wonderful.” She held the back of his head and they kissed. “I love you, Jeff,” she said as she caressed his shoulder blades and buttocks. Chelsea began rocking her hips. “Mmm ... When I move like this I get some stimulation.”
“Inside or out?” he asked.
“Both ... but especially inside.”
“I must be up against your prostate ... or, whatever is left of it after all the hormones.”
“It feels really good.” She continued rocking her hips.
Jeff lifted onto his elbows and began fondling her breasts. “What if we add this to the mix?”
“That feels good, too.” She smiled. “When you started touching me I felt you get bigger and firmer.”
“It’s what your body does to me.”
“Mmm ... feels good ... More ... Just nipples.” Jeff pinched her small but firm nipples between his thumbs and forefingers. Chelsea increased the cadence of her rocking. “Oh, God, Jeff! I’m gonna come! More!”
He added his own rocking and pinched her nipples harder. Chelsea closed her eyes, lifted her face and groaned. Jeff could feel her internal muscles throbbing against his firmly erect shaft. He began a gentle in-out thrusting, going in gently and taking friction on the pull. “Touch me,” he said.
Chelsea put her hands on his sides and pressed her thumbs against his nipples. His arousal built and he sensed his climax was near. Then, orgasm exploded in his loins. He pushed into her and grunted as he ejaculated.
“I felt that,” she said. “I felt you get harder and then throbbing as you squirted your sperm into me.”
“I felt yours, too. I could feel your muscles pulsing against me. We came almost at the same time.”
“Simultaneous orgasms,” she remarked.
“I think that’s sort of a Holy Grail of sex. I had never experienced it.”
“Until now?”
Jeff covered her cheeks with kisses and then planted a lingering one on her lips. “Until now. God, you’re such a special girl. I love you so much.”
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