Tales of Transwomen Tops Ch. 09

"Get me ready," she whispered, "But have you ever, you know, used your tongue back there?"

"I have and I'll do it for you."

She had a perfect little arse and, once I'd applied a little flavoured lube, had a great time getting her ready for me. The noises she made as my tongue pleasured her would live long in the memory, and once I had a couple of fingers inside her, she was almost begging for my cock. Lubing myself up, she gazed back and smile as I pressed against her.

"You know, once you have a girl like me, you'll never want anything else," she warned, giggling to herself.

"Would that be a bad thing, Coral? Ending up with a beautiful girl like you?"

Her lower lip trembled as she sat back to lean against my chest, turning her head so I could kiss her as I gently slid my cock inside her. She gasped as my thick head spread her before it slipped inside her, enjoying the gasp she made before another moan escaped her as I slid more of my length inside her.

"You feel good," she whispered, "And you're so gentle."

"Young woman like you... Gentle at first until you beg me for more."

Once I had my cock buried, she leaned forward and raised her arse a little more as I started to thrust away. As I'd said, gently at first as I certainly didn't want to hurt her or cause her discomfort. But the constant smile told me she was loving it, and when she started to beg for more, she got exactly what she wanted.

"Fuck me, Tom," she cried out as I leaned forward, "Fuck me harder."

"Sure you want just one night of this?" I growled.

"No... I'm going to want this more. But so will so many other girls." She moaned again as I plunged deeply. "Oh my god, that's good... You're going to get so much arse now, Tom. Now that we know you'll treat us kindly but fuck us hard."

Leaning forward more, I kissed her cheek, turning her head so she could kiss me properly. "Maybe I'll want you here again, Coral?"

"I won't say no if you wanted that, Tom."

She ended up on her back, legs spread wide as she begged me to fuck her harder, her hand furiously pumping her little cock at the same time. When she came, her arsehole squeezed me so tightly, I had to stop though left my cock buried. I think that made her orgasm feel even better. She begged me to keep fucking her again, and with a hand on her firm arm, the other laid next to her as I fucked her hard, I knew my orgasm wasn't far away.

Clutching me tightly as I filled her up, she covered my face in kisses once I was done, finally lifting my head to meet her eyes and smiling at her. Despite the fact I'd made her cum, and I'd just cum in her, she still managed to blush and look a little shy. "Okay, I'm going to need more than just one night," she admitted.

Giving me a few minutes to recover, I thoroughly enjoyed it when she had me lie back and she straddled me. Watching her bounce up and down while stroking herself off was incredibly erotic, and as we'd both cum, she lasted for what felt like an hour before she left a smaller load of cum all over my chest. Leaning forward, she then begged again for me to fuck her, hand on each cheek as I bent my legs and looked into her eyes.

"I'm going to be sore after this, aren't I?"

"We'll shower then we'll cuddle in bed."

"You'd... You'd like to cuddle with me?"

"Coral, I wasn't going to just fuck you then kick you out."

She needed a couple of moments, and I was left thinking her words about being left feeling cheap were far truer than I imagined. After we finished, then showered, I pulled her close to me once we were in darkness, and the muffled sobs against my chest, feeling her occasionally shudder, told me it had been a big night for her in more ways than one.

"I'm sorry," I whispered.

"Not your fault. Even my boyfriend didn't want to do this. He barely liked being seen out in public with me."

"His fault because you're young and beautiful, Coral."

"Tom?"

"Yeah?"

"Please talk to Chrystie. None of us will stand in her way. I got you tonight and you made me feel so loved. I'm going to tell everyone that you truly are a good man."

"There's a man out there for you, Coral, who will show you all the love you want in the future."

There was no awkwardness the next morning. Coral wanted to make love one more time, and I wasn't going to refuse her, before we dressed and I took her out for breakfast. I had no problem holding her hand as we walked down the street towards a café I knew well. I found chatting to her incredibly easy, despite the age gap of over a decade. When I told her that she had a beautiful smile, I was left wondering if she'd smile more or start to cry.

She didn't live too far away, walking her home. As she was still a student, she lived in a share-house with three others. Two were women, but I wasn't surprised she lived with another girl just like her. They were similar in many ways, and her roommate gazed up at me with undisguised lust.

"No, Dana, you can't take him upstairs so he can fuck you too," Coral stated.

"You tell him about Chrystie?"

"I think he's the only one who doesn't realise how much she likes him."

"She's a bartender. I thought she was just doing her job."

They looked at each other. "Men. Always oblivious," Coral said. She hugged me tightly, kissed me cheek, then she released a sob and hurried inside with a whispered goodbye, leaving me standing there with Dana.

"She's crying because she's happy," Dana explained, "That was a good sob. Every other time she's come home, they broke her heart that little bit more. Don't suppose you know any other men like you?"

"I do, I'm not sure how open-minded they are regarding, you know, certain things."

"Like the fact I'm a girl but still have a cock?"

"Yeah."

"Did you mind?"

"It was different. And Coral is a beautiful young woman. I hope she finds a man that will genuinely love her for her."

Dana leaned up to kiss my cheek. "Thank you for making her feel special. And I'm glad you're in a good place again, Tom. Everyone is."

"Everyone?"

She grinned broadly. "We all love you at the pub, Tom. You're one of the good guys."

Returning to the pub a couple of days later, I arrived before the doors were open and knocked. I knew Chrystie was by herself for the first hour or so after opening, the pub was open every day except Monday, and she was rarely seen on a Tuesday. Those two days were her weekend. She opened the door and smiled, apparently not surprised to see me.

"Come in, Tom," she said in that wonderfully soft voice of hers.

It was weird being in the pub when it was closed. Quiet. Very clean. Chrystie took my hand and led me towards one of the booths, sitting me down as she headed towards the bar, returning with a glass for each of us. Sitting down opposite me, she opened the bottle and poured us each a glass, each of us taking a sip before I cleared my throat.

"Six months, Tom."

"What?"

"Six months. Have fun for six months. You deserve it after everything. There are so many beautiful young women in here who are head over heels crazy for you. And everyone was talking to Coralyn on Sunday afternoon. She didn't divulge too much, but no-one smiles like that unless they were shown all the love in the world the night before."

"Chrystie... I know how you feel..."

"Coralyn told you?" Nodding just made her laugh. "And you had no idea?" Shaking my head made her laugh a little more. I didn't mind. "Guess I'm just more subtle than I realised..."

"Or I didn't want to realise because... you know..."

"Don't want to be hurt again?"

"Although I've moved on, it's difficult to open yourself up. Coral managed to pierce the armour." Pausing, I sipped at my drink. "Why six months?"

"Because you deserve to have six months where you can have fun, Tom."

"I'm not after that, Chrys. I loved being in a relationship. I loved being married. I loved having a woman to call my wife, to share that bond, to share my life with them. I don't need nor want six months if I know someone has feelings and cares for me, and the last thing I want to do is hurt them in the process." I took a chance, leaning forward to take her hand. "Chrys, we know each other, but it still feels somewhat surface level. You know my story, but I don't..."

"I'm trans, Tom. I'm a transwoman." Smiling had her smiling back in a few seconds. "Figured that out, at least?"

"Honestly, it was only because you're taller than average. Otherwise, I think you're a stunning woman, Chrys."

"You think so?" she asked softly.

"I've loved all our conversations. The light flirting. The fact you just seemed to genuinely give a shit. You gave me a reason to smile again, Chrys. It's why I'm in here a few times a week. Seeing you at the end of the day means it stays bright until I go home."

"But you think I'm stunning?"

"I'm going to put it very bluntly, Chrys. You're absolutely fucking gorgeous. I've been attracted to you for months, but I didn't want to presume on anything. Too many men take a waitress or a woman behind the bar being friendly as a sign of being interested when, in fact, they're just doing their job."

"Tom, I want to take you out on a date."

"Okay. When?"

"Saturday. I can't remember the last Saturday I had off. Guess I haven't really had a reason until now."

"Been single for a while?"

"Too many men want me for one reason. I'm a kink. A fetish. Something to cross off their bucket list. They forget that I'm a human being too, with feelings, and needs, and desires, and..." She trailed off. I was out of my seat instantly, sliding into the booth on her side to give her a hug. When she turned and held me tightly, I had a feeling that she had a lot to say and share with someone she could perhaps trust for the first time. "I want to find someone who'll just love me for who I am," she finally whispered.

"I'm thinking dinner, drinks and dancing, Chrys. How does that sound?"

"Like a wonderful night out with a very handsome man."

I popped into the pub every night after that. Coral wasn't a regular visitor but did turn up on Friday night, immediately coming to my side and kissing my cheek. "Everyone knows about your date. Just treat her right, Tom. She's strong on the outside, but we know how fragile she is inside."

Saturday couldn't come quickly enough for either of us. We'd swapped numbers the morning we'd finally confessed that we did like each other, and she must have sent me over fifty messages every day while I was work, and when I arrived at the pub, she'd ignore everyone else until I was sat down, and she'd served me a drink. The third day of arriving, I gestured her closer with a finger, kissed her cheek and whispered that she looked beautiful.

It was mid-morning on Saturday when she called. "I'm so nervous, Tom... Are you sure..."

"Not another word, Chrystie." She would have heard my serious tone. "I'm taking you out tonight and we're going to have a fantastic time together. You're going to look absolutely beautiful on my arm, and at the end of the night when I drop you home, I hope I do get a kiss."

"Tom..."

"Yeah?"

"I... I really like you already. I just hope... I mean..."

"Chrys, I really like you to. You're already a good friend. I'm hoping, in the end, we'll be something more. But we'll take it slow."

She lived in an apartment above the pub. Thankfully, there was a rear entrance, so I didn't have to go through the pub or anywhere near it when picking her up. Opening the door, she looked fantastic in a red dress that was tasteful and elegant, and she was even taller in her heels. She'd styled her hair and surprised me by wearing glasses. "I usually wear contacts," she explained, "But I want you to go out with Chrystie, your future girlfriend, not Chrys, the barmaid."

"Future girlfriend?"

"I would say future wife, but I don't want to sound too confident."

"I love the glasses. Honestly, a ponytail and glasses is my kink. Very vanilla, I know."

She stepped closer, having to lower her eyes with her heels on. "I can do that for you later... When I'm down to my lingerie later..." Then she kissed me and in that one kiss, I realised how much she did like me. What surprised me slightly was the fact she took control, and I did like it, ending up back against the wall with her body pressed against me, her tongue exploring my mouth before she finally pulled back. She smiled again before adding, "I do like being in control."

"Fine by me, Chrystie."

I didn't want us hanging around the area so had organised for us to head towards Darling Harbour. Plenty of places to eat and drink about that, much of the area going under refurbishment as it was starting to look a little out of date. The restaurant I'd chosen served simple but filling food, also affordable considering the area. For drinks and dancing, we didn't keep to one place, moving from venue to venue. Another thing I learned is that Chrystie had moves on the dancefloor.

We pulled up stumps at around 1am or so, calling an Uber to take us home. I wasn't sure if she wanted to go back to mine, so I had the driver take us to her place first. Noticing where we were heading, she placed a hand on my thigh. "We're going back to yours, Tom," she whispered, "I want to cuddle all night."

A few minutes later, I was leading her into my apartment, not surprised that the first thing she did was take off her heels. I always kept wine in the house, grabbing that from the fridge and a couple of glasses, finding Chrystie on the lounge with her legs curled up, smiling as I offered her a glass of wine. We kept the conversation light as we sipped at our glass until they were empty.

"Tom, I must tell you one thing before we start our sexual relationship." She took a deep breath, so I took her hand, feeling her squeeze it in return. "I don't want to have sex tonight."

"That's fine. You said cuddling, I can do cuddling."

"When it comes to sex, Tom... I like to be in control. I like to..." She sighed again. Turning towards her, I leaned forward and kissed her. "I'm a woman, Tom, but I love to use my cock. Do you know what I mean?"

"You want me to bottom?" Nodding, I smiled before kissing her again. "That's fine with me."

"It is?"

"Sure, and I'll let you in a little secret. My ex-wife and I experimented and one thing we tried was pegging. I enjoyed it, but only as something to do on occasion."

"Was it why you divorced?"

"No, she was fucking other guys. And when I say fucking, I mean... She was the dominant one."

"But you really don't mind?"

"No, Chrys."

Leading her to my bedroom, she enjoyed undressing me, her fingers caressing my body, almost cooing at my physique as a year and more of gym work had certainly toned me up. When she had my boxer briefs down around my ankles, her eyes lit up as I was rock hard, and I'd never had complaints. Joking about why Coralyn had been smiling so much earned me another kiss.

Returning the favour, the lingerie she wore was spectacular. She had small breasts that suited her frame perfectly, but it was when I pulled down her panties and her cock popped free that I was in for the biggest surprise. On my knees, it looked enormous from that viewpoint.

"Wow," I whispered.

"She's pretty big," she replied, chuckling to herself, "So many guys want a girl with a big cock until it comes to the moment of reckoning."

Once she was as naked as I was, we slid under the blankets as we cuddled and kissed for quite a while. Feeling her hard cock pressing into me was something new, and I couldn't resist taking it in my hand and giving it a few gentle squeezes. "Coralyn mentioned you were curious," she whispered, "Will you want to blow me?"

"Of course. I haven't done it before, but I'd love to try."

"And you're sure you don't mind being on the receiving end?"

"Not at all. All I know is that a beautiful woman would be making love to me."

"Are you sure that you don't want those six months? Once we make love, Tom..."

"Chrys, we can make love now if you need..."

She cuddled into me tightly. "No... No... It's just... I've heard so many kind words before, but the very next morning..."

"You're going to wake up in my arms tomorrow, Chrys, I'm going to make you breakfast, then we're going to spend the day together. I'm going to hold your hand. I'm going to kiss you very publicly. And I'm going to show off my very pretty girlfriend to the world."

Waking up the next morning was amusing as she was spooned against me and seemed to enjoy the feeling of my cock against her. Turning around, she asked if she wanted to spoon against me instead. Smiling, I turned around as she cuddled up into my back, feeling her larger, thicker cock pressing against me. She teased me by moving it and gently rubbing it against my rosebud, and when I released a soft moan, I felt her hot breath by my ear.

"You're going to love it, handsome," she whispered, "Your girlfriend will take good care of you from now on."

"Do you... Do you bottom, Chrys?"

"I will for you, but it's not something I do often. Only for someone I might fall in love with."

Getting out of bed a little later, I made her breakfast before we enjoyed a shower together. I enjoyed washing her up and down, and I think she really loved doing it with me, spending a lot of times running her hands over my arms, chest and back. I might have been flexing occasionally as she loved feeling how strong I was.

Heading out, we spent most of the day just walking around the city, stopping for an early afternoon lunch by the harbour, enjoying a drink or two in one of the numerous pubs. We arrived back at the pub together, though didn't head in, Chrystie inviting me upstairs to her apartment, asking if I wanted to stay for dinner. Assuring her I did, we made something simple and quick together before ending up in lounge room, spending most of the next couple of hours making out like a pair of horny teenagers.

"I want to stay but I have work in the morning," I finally stated.

"You'll be in the pub during the week?"

"Of course."

"Come on Friday night and you can stay with me all weekend, if you'd like?"

"I'd love that, Chrys."

Walking through the door of the pub on Wednesday, I noticed most of the regulars fall quiet and watch me intently as I took my regular place at the bar. Chrystie was immediately stood in front of me, ready to take my order, before she changed her mind, leaned forward to grab my shirt, dragging me up and laying a kiss on me. Lasted for at least half a minute before she let me go so I could sit down, much to the cheers of everyone around the pub.

"Usual, Tom?"

"Can I have you instead, Chrys?"

She actually blushed before leaning forward. "I'm on the menu come Friday night, handsome. Right now, you need something else to wet your whistle."

"Maybe I'd like something else. Something a little different."

I enjoyed the look that briefly crossed her eyes. She knew exactly what I meant, and the idea turned her on. Leaning across to kiss my cheek, she whispered, "Would you like to come upstairs tonight?"

"Definitely."

"Then don't drink too much, handsome."

"I'll be good."

Coralyn and Dana showed up later, both looking as cute as ever, sitting to either side of me and their flirting was outrageous but humorous. Coralyn leaned in and whispered, "She looks so happy, Tom. Thank you for being you. She needs a man like you to love."

Using words like 'love' didn't scare me. I remembered being in love with my ex-wife. Such a simple feeling was something that got me through some tough days, knowing I'd be returning home to someone who, at the time, loved me as much as I loved them. Of course, during those months after our divorce, she insisted she still loved me. I just didn't believe or trust her any longer.

Chrystie would usually be there until the door were shut, then leave a couple of staff members to clean up. That night, she kept checking the time until it hit around 10pm before she walked around the bar, took my hand, wished everyone a good time and goodnight before practically dragging me to the stairway that was a secondary entrance to her apartment.