Tales of Transwomen Tops Ch. 09

As soon as we were in her living room, she sat back on the couch and lowered her panties, freeing her hard cock, already glistening with pre-cum. Sitting on my knees between her legs, I wrapped my hand around the base and just looked at it for a few seconds.

"Nervous?" she wondered.

"Not nervous. It's just I've not done it before, and I want it to be good for you."

"Tom, no matter what you do, I'm going to cum. I'll warn you when I'm close..."

"I'm going to swallow, Chrys. I want to taste your cum then swallow it for you."

I'd received enough blowjobs over the years to put what was done to me in practice. Chrystie moaned softly as I ran my tongue up and down her thick shaft. Her groin was smooth, figuring she shaved or waxed. To tease her, I moved down and gave her balls some attention, something that earned another moan and whispered approval. Back up her cock, I ran my tongue around the thick head, tasting her pre-cum for the first time.

Wrapping my lips around her cock earned a look of complete lust as I lowered my mouth and took more of her shaft. She moaned softly, her hand ending up on the back of my head, as I took as much as I could without gagging. Slowly bobbing up and down on her cock, I ensured my tongue was also pleasuring her shaft at the same time.

"Oh baby," she moaned softly, her fingers caressing the back of my head, "Oh baby, you're good. You're very good."

That made me smile, my eyes never leaving hers. The lust was obvious to see, but there was no missing a secondary feeling that I was also experiencing. I'd shut off my heart for so long that I just hoped I wasn't going to fall hopelessly for the first woman that appeared, but I had a feeling this wasn't a rebound.

Bobbing faster and faster worked, and I had a feeling Chrystie had taken me upstairs already completely and utterly turned on. Working the rest of her shaft with my hand, fondling her balls with the other, it wasn't a real surprise that she was soon warning me that she was close to orgasm.

When I felt that first spurt of hot cum explode into my mouth, I almost came in my pants, it was so exciting. I swallowed it as quickly as I could before the next spurt fired. I savoured the taste of her cum, allowing a second and third spurt to fill my mouth before I swallowed. When Chrystie came, she came hard and it was a big load, but I swallowed it all before I finally released her cock.

She was nearly crying as she leaned forward to kiss and hug me, moving up to sit next to her on the couch as she turned to keep hugging me. "Best blowjob ever," she whispered.

"Just wanted to make you happy as I'm feeling, Chrys," I whispered back.

I didn't go home that night, Chyrstie dragging me to her bedroom, where after she'd stripped me naked, she returned with the best blowjob I'd ever received. Lying back on her bed, resting on her knees between my legs, she ever so slowly brought me to the boil, her eyes never averting from mine unless she was really concentrating. I moaned. I groaned. I swore constantly. I almost told her how I really felt about her already. I think she knew already.

When it was time to cum, she swallowed every drop in return, kissing up my body to straddle my lap, her cock already hard again as we made out. When I wrapped a hand around her cock, she broke the kiss and smiled. "Again?"

"Consider it practice making it perfect. But I loved making you happy, Chrys."

Watching her lower lip tremble, I had a feeling she was an outwardly comfortable woman hiding numerous insecurities. And I understood why as I'd already done reading of all the issues a woman like her would go through growing up and then throughout her life. Rolling her over to straddle her in return made her smile, kissing down her body, giving it plenty of attention by kissing and touching her, before I moved my way back to her cock.

I made my second blowjob last a lot longer. I was surprised at how much I enjoyed having her cock in my mouth and had momentary guilt about not doing it for Coralyn. Moving my mouth slowly up and down her cock had her moaning, and she was aware I was just taking my time, savouring the connection we'd already built, and I knew I was falling for her fast.

No idea how long I sucked her cock before she came again. That second orgasm wiped her out, and after a quick shower, she fell asleep snuggling into my chest. I almost whispered that I loved her, managing to stop myself in time, though I still said, "I want to see where this goes, Chrys. There's no-one else I want to be with."

She couldn't stop smiling the next morning as I got ready for work. I had to rush home and grab some clothes, but she insisted on making me breakfast. Kissing me at the front door, she reminded me about our date on Friday night, and to bring a bag with her as I wouldn't be leaving until Monday morning. "You won't need much in the way of clothes," she added, "Because from Friday night onwards, we're making love whenever possible."

"I can't wait, Chrys."

I barely got through the next couple of days. The guys at work noticed my distraction and guessed correctly it was to do with a woman. When I smiled, they all laughed but added that they were pleased to see I was happy for the first time in over a year. I had tried not to let my personal life affect my professional life, but it had been difficult at times.

Finishing early on Friday afternoon, letting all my guys go home early as well, I headed straight home, showered, packed a bag, then headed over to Chrystie's place. She was in her apartment, not the pub, dragging me inside and kissing me with all the passion she had for me. How we didn't end up just making love on her living room floor then and there was due to us wanting to wait just a little longer.

Heading out for dinner and drinks, we stayed local, eventually finding a bar that played music that we could dance to. Wearing a blouse and skirt, I realised rather quickly when pressed against me that she hadn't tucked her cock away, particularly when she turned me around and pulled me back.

"Can you feel me, handsome?" she breathed into my ear. Managing a nod, she chuckled lightly. "Looking forward to tonight? Ready to feel my big cock slide inside you for the first time?"

"Chrys... I'm going to want it all weekend. I promise you that."

Returning to our booth, I ended up against the side as she moved into me, kissing me hard. Reaching underneath her skirt, I lowered her panties enough that I could grasp her cock, earning a moan as she pulled back slightly. Gazing into her eyes, I slowly stroked her off, almost feeling her get larger and larger in my hand. "We need to go, baby," she finally moaned, "We really need to go."

Tucking herself as best she could then grabbing my hand, she practically dragged me out onto the street. Her apartment wasn't too far away, chuckling to myself as she was doing her best to jog in heels. She eventually swore to herself, took them off, and we could move quicker.

As soon as we were in her apartment, we were all over each other, moving together towards her bedroom as we left a trail of clothing in our wake. Ending up on the bed together, she spun around and offered her cock as I felt her lips wrap around mine.

"Cum quickly then we'll last longer making love," she explained. I wasn't going to complain about the idea of sucking her cock again, swallowing as much as I could. We'd already discussed the idea of training me to deepthroat her cock, though she insisted it wasn't something she needed, far too excited about the fact I was just happy to pleasure her.

I came first and rather quickly, something she approved of as it was a clear sign of my excitement. She then took her cock away, earning a groan of disappointment that had her giggling, but she wanted me on my knees as she sat on the edge of the bed.

"I don't want you submissive all the time," she told me, her hand caressing the back of my head as I slowly sucked her off, "But I do love how much you want to pleasure me, Tom."

"For the first time in a long time, Chrys, I'm genuinely happy."

After swallowing her large load, we made out for a few minutes, my hand barely leaving her cock as I wanted her nice and hard for when she finally made love to me. Asking how she wanted me, I was surprised when she said on my back, though only after she'd had a chance to get a good look at my arse. On my knees, leaning forward with my head on a pillow, it was the first time a woman had licked my rosebud in a while, and I missed the feeling. When she slid a couple of fingers inside me, and I whimpered, I think that turned Chrystie on even more.

"So... She pegged you?"

"Yeah, a few times."

"But a dildo doesn't cum. I'm going to fill your sweet little arse all weekend, Tom."

Rolling over onto my back, I spread my legs as I watched her lube up her cock, glistening in the light of the lamp on either side of the bed. Leaning forward to kiss me, I lifted myself up enough that I could feel her press her cock against me. "I'm ready, beautiful," I whispered, her face lighting up before she pressed forward, and I felt the head of her cock gently demanding entrance.

We moaned in unison as it slowly slid inside me, running my hands up her arms to rest on her back. "Okay, baby?" she whispered.

"Keep going. I've done this before, but... You're a lot bigger and feel so much better, gorgeous."

She took her time burying her entire length as she was incredibly thick, and I knew she didn't want to hurt me. When I looked down to see her entire length had disappeared, I couldn't stop smiling as she started to gently thrust into me, and I enjoyed it even more when she grabbed my cock and started to stroke me off, whispering that she really wanted me to cum first before she really fucked me.

I knew she was pressing all the right places inside me as my cock was throbbing with excitement, and I couldn't stop the almost constant moaning, begging for her to keep going at the same time. She loved hearing it, leaning down to kiss me, stroking me faster, pumping me a little faster at the same time.

"Fuck, I love your cock, gorgeous," I moaned.

"Love it nice and deep?"

"Feels so good. I can't wait until you cum."

"You first, baby. I want you to cum hard while I'm inside you."

I lasted another couple of minutes at most, her cock still fucking me gently, before I groaned loudly and my cock simply erupted, covering my chest in cum, Chrystie continuing to stroke me until she knew I was empty of every single possible drop. Sucking her fingers dry, she moved my legs, so they were resting over her upper arms, bending me back slightly as she started to pump me hard.

"Fuck me, beautiful," I groaned as her cock really started to pump me.

"You belong to me now, Tom," she grunted, "You're mine as much as I'm yours."

Having blown her, she kept fucking me for a while until she finally warned me that her orgasm was imminent. I just gazed into her eyes and waited for that feeling of her exploding inside me for the first time. She leaned down to kiss me hard before resting her forehead against mine as I felt her cock start to throb and this warm sensation filling me.

"Oh god," she whimpered, "Oh god... Tom..."

"Don't stop, beautiful..."

She didn't stop until she collapsed onto my chest, releasing my legs so I could wrap my arms and legs around her, enjoying the fact her cock remained nice and hard inside me. She eventually had to pull out and relaxed beside me, looping an arm over my chest as she nuzzled into me. "You'll be here in the morning?"

"I'm not going anywhere, Chrys."

"And you'll stay all weekend?"

"I'll be here every weekend, if you want me."

I consider that first time making love. It was mostly tender, gentle, and the connection was deep and meaningful between us. More than once, I was ready to blurt out that I was already in love with her, but I didn't want to scare her off.

Ending up on my knees the next time, leaning forward with my head on the mattress, we groaned together as she slid her cock back inside me. And, this time, it was nothing but a hard fuck. Chrystie loved every second, particularly once she'd pretty much mounted me, really driving her cock hard and deep with every thrust. I think I impressed her when I just turned my head and begged her for more. I loved feeling her cock buried inside me. Loved her hot breath on my neck and by my ear. Loved hearing her little whimpers and moans of joy and excitement.

Slamming me harder and harder, she couldn't get going until she grunted, and I felt her cock spurting more cum inside me again. She whimpered more than once before I slowly lowered myself to lie flat on the bed, Chrystie making me smile as she relaxed on my back, leaving her cock buried and still slowly thrusting away.

"You're addictive," she whispered.

"I'm addictive? I'm going to be wanting you inside me all the time from now on."

Pulling out, we laid on our sides to face each other, enjoying a series of soft kisses but what she wanted was to cuddle with me. Asking if wanted even more made her laugh, assuring me that we could keep fucking all night if I wanted. What I did want to try was riding her, so once we had her nice and hard again, I straddled her and slid down her cock. My face must have lit up and she pulled me down to kiss me.

"You love my big cock, don't you, baby?"

"Feels wonderful, Chrys."

"Ride me until you cum again. I want you to cum all over me."

She got what she wanted within ten minutes as I stroked myself slowly, trying to time it with the way I moved on her cock. Her hands spent most of their time on my hips to keep me stable, but once I came, she pulled me forward to rest on my forearms as her hands moved down to my arse as she started to pump up into me.

I spent most of the time kissing her before she groaned and came yet again. I was rather impressed by the fact she'd cum four time in a night, and when I slid off her lap, I couldn't help chuckling as her big cock remained as hard as ever. "Because of you," she said, "I've never been so turned on by someone before, Tom."

We both needed a shower, cuddling each other as we soaped each other up, only returning to the bedroom once we were clean and dry. To my surprise, Chrystie wanted to be the little spoon, ensuring she was nestled against me before I held her in my arms. "Promise me that you'll hold me like this often," she said softly.

"Chrys, I loved holding the woman I adore in my arms."

Waking up the next morning, it was a case of blowing each other, each of us swallowing down a load of cum, before she offered to cook us breakfast. Chrystie didn't putting on anything except a robe while I only slid on a pair of easily removable shorts. Whenever I noticed she was hard, or she would part her robe to show me that she was hard, I would end up on my knees sucking her cock to completion, or we would make love and fuck. Until late Sunday night, we fucked everywhere around her apartment. Living room. Kitchen. Spare bedroom. Bathroom. And definitely her bedroom.

By the time we went to bed on Sunday night, I was feeling rather sore, to be honest, and Chrystie was laughing away, telling me that I finally caused her not to get an instant erection as she was worn out. Cuddling together int bed that night, I gazed into her gorgeous eyes, and she couldn't stop smiling.

"I love you, Tom," she whispered, "I need to say that before this weekend ends. It's been the best of my life."

"So far as I aim for them to be even better." Leaning forward to kiss her, I added, "And I love you too, Chrystie."

Waking up the next morning, I had to shower and dress for work, walking out into the kitchen to find Chrystie naked but preparing breakfast. Coming up behind her, I kissed her neck and wrapped my arms around her. "Next time we're together, you're making love to me, Tom," she told me.

"Are you sure?"

She nodded. "I'm sure you've already realised I much prefer to be in charge, but I want to feel your love in return. And as I said, I would only bottom for the men that I love."

"How many?" I asked.

She turned her head and smiled. "I've only been in love once before. He was a good man, or so I thought."

"What happened?"

"He was married with kids. I was his clueless mistress."

"I'm sorry you were on the other end. I know how it feels. What did you do?"

"Found his wife and told her everything, and I mean everything, about our relationship. She was surprisingly very kind to me as it was obvious that I was being honest that I had no idea she or the children existed."

"What happened?"

"An inevitable divorce. He tried to blame me for everything, but she wasn't having it, not when I could go into very explicit detail about our love life." She sighed and shook her head. "Like you, I found it difficult to trust someone after that. In a way, I guess we're both wounded souls."

Squeezing her tight, I whispered, "But you've made me feel whole again, Chrystie."

"I love you so much, Tom. I've loved you for longer than just this weekend."

"I just had no idea you felt this way about me, Chrys. I didn't allow myself..."

She turned around and hugged me. "I understand, Tom, but now we can be free with our feelings." Patting my chest, she leaned back and smiled. "Now my man needs to be fed before he goes off to work. When he gets back to his apartment tonight, I expect him to call. Then we need to organise next weekend."

For the next three months or so, Chrystie and I were almost inseparable. Though she still ran her pub, she started to take more time for herself, not working as many hours, usually opening it at around 11am as always, but she would finish no later than 7 or 8pm so we could enjoy the evening together. Spending an evening together usually meant dinner, whether at the apartment or at a pub, bar or café, and our sex life from that first weekend together was spectacular.

Within three months, I asked if she wanted to move into my apartment, suggesting that moving in with me would at least mean a slight separation of work and home. She loved the idea, stating she could easily rent the apartment out, and within two weeks of suggesting the idea, Chrystie was moved in with me.

She's currently sitting across from me, eating breakfast and talking animatedly about the holiday I'm planning for us. Nothing huge, just a week away up the coast. It's warm so it'll be a lot of sun, sea, sand and hopefully sex. What she won't know is that, in my luggage, will be a small box with a ring inside it. Everyone else at the pub was already aware of my idea to propose to her.

I was confident enough that she was going to say yes.