Tales of Transwomen Tops Ch. 10

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UltimateSin
UltimateSin
5,324 Followers

"You're not freaking out," she said softly, reaching back to undo her bra, flinging that away, giving me a first good look at he breasts, "You really think I'm beautiful?"

"Most beautiful girl I've ever had the pleasure of being in bed with."

She hugged me tightly, feeling her heavy cock pressing into me as I hugged her tightly in return. "I love you, Mark," she whispered, "I had such a crush on you for so long. But it turned into something so much more that sometimes just being near you hurt me so much, that I felt I couldn't tell you how I felt."

"I wish you had of done, Jade."

Sliding off my lap, we shuffled closer together, continuing to make out before we had to admit we were exhausted after a long night out. Waking up the next morning, Jade was spooned back against me, waking up and watching her sleep. I felt my heart almost leap out of my chest as I felt a wave of feelings that I hadn't felt in such a long time. She woke up a few minutes later, turning and immediately blushing as she caught me gazing at her.

"Morning, beautiful..."

"So last night wasn't a dream?"

"If it was, it was a bloody good one, Jade."

"I think we should shower then have breakfast. My treat."

Heading into her plush bathroom, she watched as I lowered my underwear, her eyes lighting up as she stepped towards me, immediately taking my cock in hand as she kissed me, forcing me back until I was pressed against the wall. When I took her cock in hand in reply, she couldn't stop smiling despite still kissing me. "We're not having sex," she stated, "But I think we both need to cum after last night."

As soon as we were under water, she kissed down my smooth chest all the way to my groin. I kept everything smooth nowadays. She didn't tease me at all, simply inhaling my cock all the way to the base rather easily. I was above average and loved feeling the tightness of her throat. I was so turned on, I was warning her within a couple of minutes that I was close, and that's when she carefully slid a finger up my arse.

"Oh fuck," I groaned as I unloaded a torrent of cum, needing to lean forward to rest my hand against the side of the stall, "Holly shit, Jade..."

She swallowed every drop before kissing back up my chest, kissing me, no doubt wondering if I was bothered by the taste of my cum. I broke the kiss and smiled. "Oh please, you think I don't drink down cum by the litre nowadays?"

"My, you have changed for the better, Mark. Want to suck my cock now?"

"I would have done it last night, Jade."

"I know you would have done."

Kissing down her body, her nipples were hard with excitement. I'd never been with a woman with fake breasts, and had heard stories, but they were definitely sensitive, enjoying the gasps she made when I sucked and nibbled at her breasts. Kissing down her body until I was on my knees, I couldn't help marvelling at her thick cock for a few seconds.

"You should have told me, Chris," I whispered with a sigh as I lowered my head, simply voicing a thought that had lingered since I'd met her last night though hoping she didn't hear, and I didn't upset her.

"He wishes he'd told you too, Mark," Jade whispered, "It was one of his many regrets."

"I'm glad Jade is here with me now though," I replied, gazing up at her, "She's beautiful, intelligent, funny, and for some reason, she says she loves me."

"She doesn't just love you, Mark. She's in love with you. Has been since she was fourteen."

Licking up and down her cock, I could taste the pre-cum already leaking out of her cock, before I wrapped my lips around her shaft and sank down it. She moaned loudly as I felt the head of her cock hit the back of my throat, and she moaned even louder when realising that I could deepthroat. Feeling her cock in my throat turned me on something fierce, gazing up her body to see her surprise. Removing my mouth, I stroked her a few times.

"Better you're with me after I have experience. At least you know I can suck your cock and I can't wait until you're inside me, Jade."

Swallowing her cock, I didn't need to use my hands, relying on just my mouth and tongue to get her off. To prove my talent, I put my hands behind my back, noticing her eyes light up as I gazed up at her. I loved making eye contact with a lover when I was going down on them.

"Fuck, Mark," she moaned, her fingers running through my hair, "You're so good. Love sucking my big cock?"

"More than anything, Jade," I replied quickly before resuming my blowjob.

"Yeah, I bet you do. Suck my cock, Mark. Swallow all my delicious cum."

I aimed on doing exactly that as her hips started to move, her fingers tightening on my hair as her cock ended up buried in my throat more and more often. My cock was already hard again. I didn't want my face fucked but I didn't want a love to just stand or lie there, I wanted them involved. My head was soon bobbing up and down on her cock faster and faster. I loved the taste of her cock and her pre-cum, and couldn't wait until I tasted her cum.

"Oh baby," she moaned, "So close."

Sealing my lips even tighter, I focused on what would be the most sensitive part of her cock, now utilising my hands, one fondling her balls, the other working the rest of her cock. It worked like a charm as I felt that first spurt of hot cum burst into my mouth, swallowing it down as she gripped my hair as tightly as possible, whimpering and moaning as one spurt after another filled my mouth.

I sucked and swallowed until she was clearly empty and even then, I didn't stop. "Oh baby," she whimpered, "You love sucking my cock, don't you?" Smiling up at her and nodding, she removed her hand but moved it to my cheek. "Okay, baby, I'm a little sensitive now."

Removing my mouth, I kissed up her body until we were eye-level, kissing her softly. "Now we wash," she stated, handing me the bodywash and a cloth, "I'm very dirty, Mark. I'm a very dirty girl."

Dressing in last night's clothes didn't bother me, Jade dressing in a sexy skirt and blouse combination, with a pair of small heels. We visited a café on the main street not far from her apartment, enjoying breakfast together, reminiscing about old times, our separate lives since leaving our old town, and what we both hoped for the future, leaving aside our own relationship.

"What are you doing next week?" she wondered.

"Going to work. I usually go out with Mike a couple of times a week. Weekend is usually planned during the week."

"Want to do something next Saturday and maybe... I don't know, meet up for dinner during the week?"

"I'd love to, Jade. You know I'd drop everything immediately to spend time with you."

Walking her back to her apartment block, we shared a very long, passionate kiss that had us both hot and horny. I was left thinking she was ready to just throw caution to the wind and invite me upstairs, but she took a deep breath and smiled. Wishing each other goodbye, we promised to talk and message each other.

Returning to the apartment, Mike was looking rather pleased with life. Pouring myself a coffee, I had to ask why he was smiling. "Just had a good night," he said, "My arse is killing me right now. Too many big cocks absolutely slamming me for hours. Nothing beats a hardcore, sweaty gangbang."

"So it wasn't just a good night," I retorted, sipping at my coffee.

"How was your night? Did you meet up with Chris?"

"It's a long story, Mike. Um... Chris isn't Chris anymore, if you catch my drift."

He knew what I meant immediately. "Ah... But you didn't come home last night so I take it..."

"She said she loves me. She's been in love with me for over ten years."

"Damn, quite the confession. What do you think?"

"Mate, I'm not entirely sure. Part of me is ready to give up everything right now to be with her. But she also said she's happy for me to keep having fun until we commit to each other. I just have a bad feeling if I were to keep fooling around, it would break her heart."

"I know Ben will be rather disappointed, but I guess if you're already thinking seriously about... What's her name?"

"Jade."

"Pretty name. Anyway, if you're thinking seriously..."

"She's my best friend and laid her heart out already. The idea of hurting her..."

Mike smiled at me. "I think you know the answer already, Mark. I think you need to make a few phone calls to make sure all your lovers know the score."

Returning to my room, I closed the door and immediately started making some calls, leaving Ben for last. He was disappointed to hear that I was bringing out fun to an end, but he must have heard in my tone my feelings for Jade. "She must be one hell of a girl," he suggested.

"She's my best friend, and I guess I have to put my own heart on the line at the same time."

"Good luck, Mark. I hope it works out for you. It's been fun. Glad I was your first male lover."

"I'm glad too, Ben. Won't forget that first morning together. Changed my life in many ways."

After ringing off, I took a deep breath and called Jade. She was probably surprised I was calling so quickly, but I wanted to let her know. "Hey, handsome. What's on your mind?"

"I've just finished calling around, Jade. I've ended everything with anyone else. I only want to be with you."

She was quiet before I heard her crying. "You mean that, Mark?"

"Hand on heart, Jade. I liked them but, compared to you, they didn't have a piece of my heart. You gained a piece last night, and I think you're going to gain the rest of it very quickly."

"Can you come around tonight, Mark? I need to see you."

"I'll come around as soon as I can, sweetheart."

"Sweetheart?"

"Need to think of a name for you if you're going to be my girlfriend."

I think she cried even more. "I've always wanted to be your girlfriend, Mark."

"Well, I think now is the perfect time to be called that then. I'll see you soon, beautiful." I paused before adding softly, "I love you, Jade."

She sobbed that she loved me before the line disconnected. I needed to wipe my eyes after that. I'd never been one to think you could instantly fall in love with someone. But I'd fallen for her hard the previous night and into the morning.

Quickly getting changed, I packed a small bag and walked out to the living room to find Mike on the couch. He took one look at me, smiled, and wished me luck. Back on the main street, I stopped at a shop and picked up some flowers. Arriving at her apartment block, she buzzed me up, riding the elevator, feeling my heart beating at a million miles as hour. I felt as nervous as I had done when walking up to Tamara's front door before our first date when we were sixteen.

Knocking on her door, it flew open within seconds. I couldn't help smiling as I offered her the flowers, that familiar tremble of the lower lip as she held them to her nose. Offering her other hand, she dragged me inside and kicked the door shut, leading me to the living room and into the kitchen. I stood and watched her find a vase, filling it with water before she unwrapped the bouquet, placed the flowers in the vase, and placed it pride of place in her living room.

She turned around and looked at me. "You said you loved me, Mark," she whispered, "Did you mean it?"

"Absolutely."

Slowly stepping towards me, she glanced at the bag I'd placed on the lounge. "Are you staying tonight?" she asked softly.

"I hope I am, Jade. I'd like to stay here quite a lot."

Wrapping her arms around me, we gazed at each other in silence for a few seconds. "I still think I'm dreaming... I'm scared I'm going to wake up, I'm still... I'm still him and you have no idea how much I love you."

Caressing her cheek, I wiped away the tear that slowly slid down it. "You're not dreaming, and what I know is that my best friend is the most beautiful woman I've ever laid my eyes on, and I have to confess that I'm falling in love with her in return."

She sobbed against my chest, holding her tight against me. "You have no idea how long I've wanted to hear you say you love me too," she said.

"I'm taking my girlfriend out for dinner tonight."

"Say that word again."

"Can I be an awkward teenager?" She chuckled against my chest, but I felt her nod her head. "Would you like to be my girlfriend, Jade?"

"I'd love to be your girlfriend, Mark."

Sitting on the couch together, she wanted nothing more than to snuggle against me. We held each other for at least an hour, a little making out mixed in with a lot more conversation. And it was amazing how quickly our talk turned serious. The one question I had was, "Your parents obviously know about changes, but I'm left thinking no-one else knows?"

"I left my life behind, Mark. You were the only one I wanted to keep in touch with." She leaned back and searched my eyes. "I do plan on returning home on the arm of the man I love. It will give me strength when I tell everyone else the truth."

Taking her out for dinner, she dressed as sexy as she did the previous night, but I knew it was only for my eyes. The restaurant I chose had rave reviews, no more than a short walk from the apartment. The sort of small, intimate place often found in areas like we lived, probably a dozen tables in total, great service, great food, and reasonable prices considering the area.

After dinner, we enjoyed a drink or two, but Jade was giving me the eye that she wanted to be somewhere else. It was still early when I whispered into her ear about heading back to her apartment. To say she dragged me back there wouldn't be an understatement. As soon as she'd closed and locked the door, she leapt on me, practically pushing me into her bedroom as our clothing very quickly disappeared.

Once her cock was free from her panties, I dropped to my knees and took it in my mouth as she finished undressing. "Oh god, baby, that's so good," she moaned, "Going to suck me until you cum?"

"Of course, sweetheart. And that's just the start," I replied, resuming my blowjob.

Her fingers ran through my hair, her smile never wavering. "You're totally getting fucked tonight. You realise that, right?"

"I can't wait, Jade. I'm going to drain you now, so you last longer fucking me."

Jade was horny as hell and was warning me she was close within a couple of minutes. I loved feeling her cock all the way in my throat, her eyes lighting up when she felt my nose bump into her groin, her entire cock disappearing, only coming into view when covered in my spit and drool.

She came hard, both hands on my head as I felt blast after blast of her cum fill my mouth, eagerly swallowing it down though savouring her taste when the last couple of spurts were manageable. Cleaning up her cock, I moved down and gave her balls some attention before I made a motion with my finger. She giggled as she moved to bend over the bed. Spreading her cheeks, I dove to give her arse some attention at the same time.

"Oh fuck," she moaned, "I had no idea you liked doing this. I'll definitely return the favour before I fuck you, Mark."

I didn't eat her arse that long, I just wanted to give her a little treat. When I stood up and removed my clothes, she stood up and kissed me, her hard cock pressing into me. "Need a blowjob too?" she wondered.

"I'll cum when you're inside me, beautiful."

"I love it when you call me that."

"Only speaking the truth, Jade."

Ending up on the bed, on my knees and pushed forward, Jade didn't hesitate in getting her tongue busy between my cheeks. I loved having my rosebud licked and Jade was enthusiastic. When she had me moaning, it earned more than one slap on a cheek before her tongue got back to work. I was so turned on, I had to jerk off while her tongue was buried.

She eventually stopped though only to apply lube and I felt her slide two fingers inside me. Moaning even louder, she leaned forward, leaving soft kisses up my back. "You really do love things up your arse, don't you?"

"I'm definitely not a virgin there, Jade."

I'll admit, I was begging for her cock within a couple of minutes. I felt her fingers disappear, turning my body enough to see her lubing up her thick cock, smiling at me as she rested it between my cheeks. When her hand was placed in the middle of my back and I felt her press her cock against me, I almost begged for her to slide her cock inside me.

Feeling her pressing forward, we moaned together as the head of her cock slid inside me, making her giggle when I immediately pushed backwards once that was in as I wanted to feel her whole length. "Easy, baby," she cooed, "I'm going to fuck you hard. Don't you worry."

"Just want to feel you inside me, all the way," I replied.

Once she was buried, I felt her shuffle to get comfortable, before she rested a hand on my hip, the other hand on my upper back, as she started to thrust. I started to whimper and moan almost immediately as it was one of the best cocks that I'd ever had inside me. "Oh god, fuck me, Jade," I moaned loudly, "Don't stop, beautiful."

When she picked up the tempo after only a couple of minutes, I was putty in her paws. Hand moving up to my shoulder, I lowered my body to change the angle as she started to drive nice and deep. I needed to stroke my cock, groaning at how sensitive I felt. Jade leaned forward as she fucked me even harder.

"Cum for me with my big cock buried," she breathed into my ear, "Do you love me, Mark?"

"Yes," I moaned.

"And do you love my big cock?"

"Fuck yes, Jade. Don't stop."

"I won't, handsome. This will be your life every night going forward."

Turning my head, I kissed her softly. "I can't wait, beautiful."

I came all over her sheets, but I don't think she cared. It was one of the best orgasms I could remember, knowing I was squeezing her cock at the same time. That just urged her on to fuck me even more, feeling her practically mount me, her head resting next to mine as she really started to drive her cock harder and faster. When I started to grunt, she left a soft kiss on my lips.

"Not hurting?" she asked softly.

"Feels wonderful, Jade. Just cum in when you need to."

"I'm close. I can't believe I'm finally inside you. I'm going to cry when I finally cum."

"Once you're done, pull out and I'll hold you afterwards."

Feeling her finally cum inside me for the first time, I felt her hot tears drip on my back as she whimpered and moaned as much as I did when she first started to fuck me. She kept pumping until her cock did start to soften, feeling her slowly ease her cock out of me, letting me roll over so she could rest on my chest and release all the pent-up emotions. She didn't say anything for quite a while, seeming to simply enjoy being in my arms, my fingers running up and down her spine, though I did start to chuckle when I felt her cock start to stiffen rather quickly.

"You've always turned me on, Mark. I used to masturbate all the time thinking about the naughty things we could do together."

Sitting back on her knees, she applied some more lube to her cock, spreading my legs nice and wide so she could slide her cock back inside me. Leaning forward once it was buried, I can say that this second time was making love. It was tender and gentle, our eyes and body language expressing all the love we felt for each other. Our mouths only parted when we needed a deep breath or release a moan or a groan.

I loved gazing into her eyes. I loved looking at her pretty face. I loved her breasts and her toned body. I loved her arms as whenever she cuddled me. I loved her arse, trying to remember if I ever checked out my best friend before the transition. I loved her legs and her feet. I loved her cock. Definitely loved her cock.

We made love for at least an hour, long enough that I could cum again, this time Jade stroking me off as she slowly made love to me, erupting all over myself, Jade removing her cock so she could position herself to clean me up with her tongue. "Yummy," she stated, "I'm definitely going to blow you as often as you do me, Mark. I loved sucking your cock in the shower."

UltimateSin
UltimateSin
5,324 Followers