Tales of Transwomen Tops Ch. 10

He departed by midday with Peter, both of them leaving their number with us. Once they were gone, Mike turned and couldn't stop smiling. "Want to do that again?"

"Hell yes. Guess I've learned something about myself in the past twenty-four hours."

Though I did go a little wild for a few months, I actually enjoyed my time with Ben every few days. Neither of us was interested in a relationship, as I knew he had other lovers on the side, but when Ben did come around, he spent most of the time with his cock buried inside me, usually in my arse but I did enjoy going down on him.

As for Mike, we'd occasionally swap partners as we'd both be on his bed, heads on the mattress as our arses were fucked nice and hard. He even introduced me to group sex, inviting more than two men around for some fun of an evening. Feeling one man after another dump his cum inside me was thrilling, and I quickly had any thoughts of meeting a woman at the furthest reaches of my mind.

What I realised is that, since that first time with Ben, I'd never been what was called the top, I was always the bottom, and I found that I thoroughly enjoyed it. Mike was a complete bottom as well, but I'll admit that we occasionally fooled around, happily sucking each other off to orgasm if we had a night where we didn't have anything planned.

It was perhaps six months after I'd moved in with Mike that I received an email from Chris. I hadn't heard from him in well over a couple of years, so I was rather surprised. Even though I still considered him my best friend, I was left thinking the lack of communication from his end meant he'd simply moved on.

Hey Mark,

Sorry I haven't been in touch for so long. I've received all your emails and I loved hearing all your stories, particularly of your time in the army. I've been reading your last email about moving to Sydney and I thought it was about time I got in touch. I would have done so earlier, but my life has been so hectic lately and I only wanted to meet once I was sure I had all the time in the world to give my best friend.

We are still friends, aren't we? I hope we are. I've missed you, Mark. More than you can probably imagine.

I read that and, for a guy, it was rather intimate. Chris and I had always been close growing up, but there was something about his writing that had me wondering.

I would love to see you again, Mark, I know that much. I'll leave my number at the bottom of this email. Phone, text or message me via one of those apps, I really don't mind. I would like to hear that voice of yours again though.

Now alarm bells were ringing. Maybe Chris has discovered a side to himself too? And if he had, was he signalling an attraction to me? We hadn't met in person for eight years, but we were friends on social media, so he would have seen quite a few photos of me.

I hope to hear from you soon, Mark.

Lots of love,

Chris

Underneath that was his phone number and a number of other ways to reach out to him. When I checked his social media, it hadn't been updated in years so there was nothing to tell me if he was seeing someone, if he'd come out of the closet, or perhaps he was just a man comfortable enough to confess feelings of missing someone who had once been so close to him.

Ben was around that night, on my back as he fucked me nice and hard, but he could see I was away with my thoughts. He kissed me hard, which brought my mind back, grinning at him as I felt him dump his third load of the night inside me.

Leaving his cock inside me, he asked, "There's something on your mind, Mark. What's up?"

"Sorry, it's just... I got an email from a friend, and it's got me wondering."

"What did it say?" After giving him the gist of it, he grinned. "Well, sounds like someone might have come out of the closet and might want to have a private chat with an old friend." He leaned down and left one hell of a kiss on my lips. "Considering you're completely bisexual nowadays..."

"Yeah, can't get enough of someone's dick."

"Not just mine, from Mike's told me."

"Jealous?"

He thrust a couple of times, making me moan. "Nope, because I get to fuck you often enough."

Leaning down, he had my legs back as he resumed fucking me. "Fuck, I love your dick, Ben," I groaned, "Fuck me harder."

Half an hour later, I was on my knees with Peter in front of me, swallowing his cock as Ben buried his cock faster and faster, Mike watching as he loved seeing me spitroasted, and we'd swapped partners often enough now that there was never any jealousy. Watching Mike take two cocks in his arse at once was something else entirely. I'd seen him do it quite a few times...

Once Ben and Peter left the next morning, I opened my laptop and started writing an email back to Chris. Mike sat next to me on the couch, leaning against me, as he read my words.

"Think he definitely fancies you, Mark."

"Would be a bit weird if I ended up in bed with him. I mean, we've known each other since we were five years old. I haven't seen him since we were eighteen. We've both changed a lot, it seems."

Sending off the email, I wasn't surprised that I received a message back on my phone within five minutes. It was from Chris. It was a long message and it had me smiling, as he spoke about how much he wanted to see me. He admitted not wanting to call as he was too emotional. I replied, asking when he would like to meet.

His reply was immediate. At a nearby pub on Friday night. That was only a couple of days away. Asking if I'd recognise him, he assured me I'd know it was him when I saw him.

I could barely concentrate at work on Friday, feeling butterflies in my stomach. I'd never been attracted to any man while growing up, always been about girls. I still marvelled at how quickly my world turned upside down after that first night with Ben. When he slid his cock inside me for the first time that morning, I knew in that moment I was bisexual. I still desired a woman to be romantic and start a family with, but if I couldn't find one, I'd happily spend time in the company of men.

Leaving work a little earlier than normal, I arrived home to find Mike already on the couch. Heading to the shower, I wasn't surprised when he joined me, though was surprised when he fell to his knees. He swallowed my load within five minutes. "That'll take the edge off," he stated.

"Thanks. I'm feeling like I'm about to go on my first date with a girl."

After I'd dressed, applied my favourite cologne, and made sure I was looking good, Mike looked me up and down, returning a thumbs up. Grabbing my phone, wallet and keys, Mike walked me to the door, wishing me lucky. "And if you bring him home tonight..."

The pub where I was meeting Chris was only a short walk away. Heading inside, I bought myself a beer and found a free table. I'd been in the pub often enough that I was a familiar face, one or two regulars asking where my usual partner in crime was. I assured them he'd be in later as he was always cruising for cock, whether it be new or someone he had fuck him regularly.

It was mostly men who would walk through the main door though the occasional woman did. Most were lesbians, the occasional transwoman, and then there were those who I couldn't figure out if they were a man, woman or something in between. Even though I now considered myself somewhat bisexual, I still didn't understand all these new sexualities and genders, but I was open-minded and lived by the motto 'live and let live'.

Watching one of the televisions on the wall, I didn't notice the presence of someone next to me until a breathy voice said, "Hello, Mark."

Turning my head, I looked up the body of a woman in a red dress, a pair of rather large breasts, before I greeted by a very pretty face, framed by some rather blonde hair, faint freckling over her nose and across her cheeks, and a pair of the most gorgeous blue eyes I'd seen in a long time. And it was the eyes that had mine widening in surprise as I stumbled to my feet. She smiled at me rather shyly, her hands fidgeting as I knew she was nervous.

"Chris?" I asked softly. Shaking her head, when a couple of tears slid down her cheeks, I stepped closer. "Um, did you used to be Chris?"

"My name is Jade, Mark," she said softly, "But I'm still your best friend. Am I still yours?"

Taking her hands in mine, I was surprised at how soft they were. She stood a couple of inches higher, glancing down to see she was wearing heels. She stepped closer to me, her eyes gazing into mine. Lifting a hand to stroke her cheek, her lower lip trembled as her eyes started to glisten again. "Why didn't you tell me?"

She choked back a sob and collapsed against me. "I couldn't," she said after a few seconds, feeling her hands grabbing my shirt, "I couldn't because you were my best friend, but I was in love with you. I thought I was gay and that you'd hate me for it."

"Jade, I'd never have hated you for being gay."

Glancing around, everyone watching us though their eyes reflected understanding. Stroking her back, she sniffed a few times. "When I was at university, it was there that I finally realised more about myself that I'd kept supressed. I always thought I was just weird, but I used to... dress up in my mother's clothing and I always wanted to be a girl, Mark. I was... I was undergoing therapy the last two years at school."

"You were?" She leaned back and nodded, wiping her cheeks with my thumb. "Jade, you were my best friend. I would have understood."

"I couldn't take that chance. We lived in a small town. I was surprised you didn't hear about it despite my family keeping it a secret. When I got to the city, I could live as a woman full time and have done ever since I arrived."

"You look beautiful, Jade." A shy smile formed as she looked away. Lifting her chin with a finger, I made sure her eyes met mine. "I mean that, Jade. You're stunning."

She kissed me, her lips incredibly soft and I could taste flavoured lip gloss. When her tongue slid into my mouth, I wrapped an arm around her, pulling her close. There were some cheers around us, but I ignored them, Jade eventually breaking the kiss and resting her head on my shoulder. "I never forgot you, Mark," she whispered, "And I never stopped loving you. I've loved you for so long, it... It hurt to think about you."

"I didn't know, Jade."

"It's okay. I was a mess for a long time anyway. Probably wouldn't have made a good boyfriend or girlfriend at the time."

I hugged her for at least a few minutes, feeling her relaxing in my arms before I leaned back and kissed her again. This time, my tongue slid into her mouth as she pressed her body against mine. When she moaned, she broke the kiss and giggled. "I think someone is excited by the new me," she whispered.

"I have quite a lot to tell you too, Jade. But first, I need to buy the lady a drink. What would you like?"

"A cocktail. Something sweet but alcoholic..." Then her lower lip trembled again before she hugged me tightly. "Fuck, I've missed you so much, Mark. I'm sorry for being a mess. I love you."

"Jade..."

"It's okay, Mark. I know your feelings for me would be different. I just had to tell you. I kept so much repressed. I... I wanted you to be my first, that's how much I loved you."

Hugging her in silence, I gave her a few minutes to calm down before I escorted her to the bar. After buying drinks, I looked around for a table that offered more privacy than the one I'd been sitting at. There was one in the corner, pulling out a chair for Jade before I took a seat. When she placed her free hand on the table, I took it in mine, interlacing our fingers, earning an instant smile.

"Your email had me thinking you were gay, Jade. I'm sorry that I was still calling you your old name."

"That's okay, Mark. I didn't want to tell you over email. You deserved to be told in person."

Squeezing her hand, I said, "I was honest about one thing. You are beautiful, Jade. I mean... Just wow."

"Thank you, Mark. You're looking rather rugged and handsome yourself. The army did you wonders."

"Not just that. I've found that I've thoroughly enjoyed living in the city and, well, I've learned one or two things about myself."

"Such as?"

"I'm bisexual."

"You didn't learn that in the army?" she asked, giggling to herself, "I thought half the army was at least bisexual."

That had me laughing too. "No, I learned within a week of moving here that I didn't mind the company of men. And for the past six months, I've only been sleeping with men."

Jade's smile was broad. "Six months of only cock? You've gone gay on me, Mark." Sipping at her cocktail, I raised my eyebrows when I felt one of her feet caressing my legs. "So are you a top of bottom?"

"Honestly?"

"I'd expect nothing less."

"I'm a total bottom, Jade. My god, the feeling of a big, thick cock inside me, just pumping away for as long as they can last until they dump their enormous load inside me... Gets me hard just thinking about it."

Saying those words had her foot between my legs, caressing the erection that had formed rather quickly. "Well, I love what I can feel there, Mark. Tamara always suggested you had a nice big cock. Had me wondering if you'd want to top me if I'd ever confessed how I felt."

"Would you have wanted me to?"

"A large part of me wanted to be a woman but still fuck you hard, Mark," she almost growled, before she started to blush, clearing her throat, "Sorry, it's just... Seeing you again, looking as handsome as hell, I'm actually rather horny right now. Crying then horny is a weird combination."

"You hungry?"

"Starving. Should we order a plate to share? You can feed your date."

"You're my date now?"

She leaned forward as I did, sharing another kiss. "Maybe ten years too late for my liking but this is definitely a date, Mark." Her hand caressed my cheek, her blue eyes gazing into mine, and I knew she was still in love with me to this day. "You're not getting lucky tonight though. It's too soon. I'd be an emotional wreck."

"Will you want another date?"

Her face lit up in a smile. "Are you asking me out on another date already, Mark?"

"Definitely."

"Haven't even finished this date."

"Already know I want to take my best friend out on another date, Jade." That lower lip started to tremble again, moving to the chair next to her so I could kiss her far easier, her hand ending up on the back of my head as we made out for a few minutes. "Think that proves what I think of this relationship already..."

"Relationship," she whispered, "I like the sound of that already..."

After enjoying dinner, she asked if I'd take her out for dancing. I avoided my more usual haunts I'd attend with Mike, finding another place that was still crowded but had a more mixed clientele. Finding a booth, we sat on the same side, her hand on my thigh as we sipped at our drinks and continued to catch up on each other's life.

"So this Ben that's fucking you. Is it serious?" she wondered.

"No. He's just got a nice thick cock and he loves to fuck me."

"Would he be upset if you ended things?"

"I'd be a little upset, to be honest, though that's just because he was the first guy I was with. But he'd understand if I met someone that I wanted to be exclusive with."

"I don't expect exclusivity yet, Mark." She turned my head to kiss me. "I just want to date you a few times, make sure it feels as right as I've always thought it would be."

"You sure? I mean, I don't just sleep with Ben. Well, sleep isn't right. I've got three regular guys who love to fuck me."

"Tart," she joked, giggling to herself, before she kissed me again, gazing into my eyes, "Would you really stop everything immediately for me?"

"You're my best friend. If you asked me to do that, I would do so in an instant."

She hugged me tightly before she kissed me again. "Thank you, Mark. Want to dance?"

"Definitely."

Moulding her body against mine, I ran my hands up and down her back before I just had to get my hands on her arse. She smiled when I gave each cheek a gentle squeeze. "That's one hundred percent mine," she whispered, "Always thought I had a nice arse. Ever check my arse out, Mark?" She made me laugh before pressing her chest into me. "These are fake, of course. Didn't go completely bimbo but I wanted a nice set of tits. And I've obviously had a little work done to my face."

"If I look at you long enough, I see... you know..."

"I don't mind if you see me," she whispered, "I'm no longer him, but I still have the same heart. And my feelings never changed despite everything."

"Jade, one question I know about trans issues. Have you gone through with it?"

"No, and I have no intention of doing it either. I don't need to lop it off to feel like a woman. I don't hate my cock. I still like using it."

"You do?"

She leaned forward, her lips by my ear. "I love using it with certain men," she breathed, biting my earlobe, "Hearing you love to bottom turns me on something fierce, Mark. Kind of wish I'd made my move years ago. I'd have pumped your lovely arse full of cum for years."

"You still get hard?"

"Hard as fucking titanium, and I still cum in buckets," she breathed, "The idea of fucking you makes me want to free my cock and show you how big I am too."

"I'd do more than just look, Jade."

We danced and drank until the main lights turned on and they rang the bell for last drinks. Checking the time, we both blushed as we'd completely lost track, lost as we were in the company of each other. Quickly finishing our drinks, I offered to walk her home, Jade delighted as she wrapped her arms around one of mine as I found myself walking in the opposite direction to my apartment.

It was only a fifteen-minute walk to the lobby of her apartment block. Stopping outside, we turned to face each other, not hesitating in sharing another passionate kiss. She smiled while kissing me as my erection couldn't be avoided while I just had to get a feel of her arse once again. When we finally came up for air, she stroked my cheek again. "So handsome," she whispered.

"And you're absolutely beautiful," I whispered back.

"What are you thinking right now, Mark?"

"That I'd love to go upstairs with you tonight and never look back."

She took a deep breath, her hand not moving from my cheek. "You can come upstairs but we're not having sex, Mark. I can't do that yet. When we make love..." I smiled immediately at that term. "That's what we'll be doing, Mark. Making love. But I don't want to rush into bed with you, because once we sleep together, that's it. You're mine for the rest of my life. I'm not letting you go again."

Taking my hand, she led me inside to the elevator, not surprised she lived in a top floor apartment. It was exquisitely decorated, kicking off her heels as soon as we were inside so she was now an inch shorter, just like I remembered. Leading me towards the couch, she sat me down and disappeared into what I assumed was the kitchen, returning with a bottle of beer for me and a pre-mixed drink for herself.

Our drinks were ignored almost right away as we resumed making out. My hands ended up feeling her breasts and arse while she couldn't resist caressing the bulge in my pants. She finally stood up and lowered her panties, throwing them onto my face before she sat down, and I noticed the significant bulge now underneath her dress. Resuming our kiss, my hand went straight for it.

"Not too much," she breathed, "Or I'll cum so fast."

We finally stopped making out and had a drink, but we barely drank half our bottles before I found myself dragged to her bedroom, where our clothing except my underwear was taken off. Pushing me onto the bed, she joined me quickly, straddling my lap, her cock hard and I noticed immediately it was larger than mine. Larger than most of my lovers, to be honest.