Tales of Transwomen Tops Ch. 06

"It's okay," I assured them both, taking a deep breath, "She feels just as wonderful as you felt, Miss."

Miss Anderson didn't waste any time thrusting into me, her skin slapping against my arse as she figured out a tempo that suited us both rather quickly. With a hand on my shoulder and another at my hip, she was burying her cock nice and deep with every thrust, my cock already hard again. I moaned and groaned my way through it, either resting my head on the lap of Miss Rodriguez or glancing back to watch Miss Anderson thrust into me. Miss Bailey eventually sat up on her knees next to us and I could use my hand to stroke her off too.

"Fuck, he's so tight," Miss Anderson groaned, "How did you last so long, Josie?"

"Kissing him all the time distracted me."

Miss Anderson pulled me back, so my back rested against her chest, feeling her hard nipples against me, as she turned my head to kiss her. "You're so fucking cute, Stevie," she whispered, her smile ensuring she looked so beautiful, even when fucking me, "We've been waiting for someone like you."

"I've been waiting to meet girls like you."

Kissing me again, she gently pushed me forward and moved to mount me, her head on my shoulder as she started to drive her cock into me. I whispered that it did hurt a little bit but that I could handle it as it felt so good when driving her cock deep. She kissed my cheek and assured me she was going to cum quickly. "Can't wait until you fill me up too, Miss," I told her.

Hearing her groan as she unloaded in my arse after barely another couple of minutes was a major turn on. Leaving her cock buried for a couple of minutes, I was eventually pulled back again to rest against her body, her hands running up and down, whispering about how soft my skin felt. Then she hugged me as Miss Rodriguez sat up and hugged me as well.

"Her cock is still inside me," I told Miss Rodriguez, which made both of them laugh.

"Just because we want to fuck you doesn't mean we won't want cuddles too, sweetie."

Miss Anderson pulled her cock out of me as I relaxed down on the bed next to Miss Rodriguez, lying on my back again as Miss Bailey positioned herself between my legs. "Need a break, sweetie?" she asked.

"No, Miss. I'm ready for your big cock too. How do you want me?"

"We're making love, sweetie. Exactly how you are is just the way I want you."

Moaning as she easily slid her cock inside me, giggling as she joked about all the cum currently inside me, my legs ended up hooked around her elbows as she didn't have to take too long building a good rhythm that felt wonderful for us both. Miss Anderson and Miss Rodriguez cuddled into either side of me, kissing my cheeks and neck as Miss Bailey occasionally kissed me but liked resting her forehead against mine as she fucked me faster and faster.

"Do you love being fucked, sweetie?" she asked.

"I'm living my dream right now, Miss," I replied.

"And there are two more teachers who'd love to join us."

"And we can get some other friends involved," Miss Anderson added, "If that idea doesn't scare you, sweetie."

"Girls like you?"

"There are more girls like us than you probably realise," Miss Rodriguez replied, "Beautiful women with big cocks who love to fuck cute young men, just like you."

Miss Bailey really started to fuck me faster and faster, both of us moaning as her kisses increased in passion and intensity. I moved my hips in time with her thrusts, soft hands of Miss Anderson and Miss Rodriguez caressing my body at the same time, both reaching down to gently stroke my cock occasionally.

"Don't want to cum too quickly," Miss Bailey finally grunted.

"We'll get plenty of time with him this year, Courtney," Miss Anderson said, chuckling to herself, "And his arse is so lovely and tight, it's little wonder I didn't last too long."

"We're really going to share him?" Miss Bailey asked, glancing at Miss Rodriguez.

"I promise that we'll have times with him together, and there'll be times when he's at one of our places to make love alone. And it's also up to him too."

"I hope you share me as I really like you three already."

"There we go, Courtney. Steven wants us to share him too."

Miss Bailey took a few more minutes before she needed to cum inside me. Once her cum had joined the others, she pulled out and I turned to Miss Rodriguez, admitting I would need a break now. I'd been a virgin, just been fucked three times, and I needed a good break. The three all hugged me together, thanking me for allowing the three of them to all have their chance so quickly.

Miss Rodriguez led me to her ensuite bathroom as the other two disappeared to the guest room. We had a quick shower, Miss Rodriguez carefully washing me up and down, her eyes constantly gazing into mine. "Miss?"

"Yes, sweetie?"

"I... I, um..."

She stopped washing me and kissed me softly. "Those feelings are natural after your first time, sweetie. The first time I made love with a boy, not long after I turned eighteen, I thought I felt that way."

"Did you?"

"I did but his feelings were not returned. Unfortunately, he was one of the many men who couldn't handle being fucked by a woman. It's why I'm careful now and, well, I usually look for younger men."

"How old are you, Miss?"

She smiled as she resumed washing me up and down. "I know you're eighteen, sweetie. Rest assured that none of us are more than ten years older than you."

"I wouldn't have said any of you were older than twenty-five."

"And you're just trying to prove how big a sweetheart you really are."

"Just being honest, Miss. Like me admitting that I've absolutely loved today, and I'll want to keep doing this with you..."

She kissed me softly before we cuddled again. "We're going to have a wonderful year together, sweetie. I promise."

We ordered in dinner a little later, the four of us putting on some clothes for when the delivery was made. Gathering in the living room to eat, we polished off everything before following that up with another couple of glasses of cocktails. As the three women sat together on the couch, sipping at their drinks, I took pleasure in working them with my mouth and hands.

"Make the two of them cum," Miss Rodriguez told me, "We'll fool around in bed when it's time to go."

Miss Bailey was happy I focused on her first, head bobbing up and down on her lap, though I kept working Miss Anderson with my hand at the same time, before she told me to just focus on Miss Bailey. After earning quite a load of cum from her, she relaxed back and smiled as I moved across to give Miss Anderson more attention.

"Want to ride me, sweetie?" she asked after a few minutes.

Glancing at Miss Rodriguez, she chuckled at me. "Sweetie, you don't need permission from me to do anything. If you want to ride her big cock, go for it."

Stripping off, she lubed herself up as Miss Rodriguez did help me get ready before I positioned myself on Miss Anderson's lap, grabbing the base of her cock and prodding the head against me. Taking a deep breath, she replaced my hand as I ever so slowly started to slide it inside me, kissing her hard as I felt her thick cock spread me wide.

Took a couple of minutes before she was buried all the way inside me, but once we were both comfortable, I had my hands on her shoulders and was happily bouncing away, with her hands on my hips as she thrust up into me at the same time. It felt wonderful as I made out with her at the same time, and as I rode her faster and faster, I was caught by surprise when I erupted all over her chest.

"That's it, baby. Cover me in your spunk!" she cried out.

"Holy shit!" I groaned as I hadn't even realised that I was close to orgasm.

To my surprise, she easily picked me up and we switched position with me resting back on the couch, my legs once again spread wide as she really upped the tempo of fucking me, driving her cock deeper and deeper with every thrust. Her blue eyes were alive with the lust and desire she felt for me, her dark hair plastered to her forehead, her body glistening with sweat as it was still rather warm that evening.

"Going to cum in me again?" I teased.

"I'm going to cum on your face when I'm ready."

"Courtney..." Miss Rodriguez warned.

"I'm not going to fuck his face or anything. I'm just going to jerk off onto his cute little face. Would you like that, sweetie?"

"I'd like to try, Miss."

"Good boy. Now I'm going to fuck you nice and hard for the next couple of minutes. When I'm ready to cum, you'll get on your knees and get ready for an explosion."

Waiting on my knees when she was close to orgasm, I watched her stroke herself faster and faster, opening my mouth and closing my eyes when she was ready to erupt. Feeling her warm cum land all over my face made me giggle, and I probably caught her by surprise when I didn't hesitate in sucking her cock to clean up her cum when she'd stopped spurting on me.

"Good boy," she whispered, leaning down to kiss me, feeling a cloth help to clean up my face rather quickly, "Did you like that, sweetie?"

"Yeah, I've always wondered what it would be like."

"We're going to have a lot of fun together, Stevie. And when we're alone, we can really experiment, but we'll never do anything you don't want. I promise."

It had been a long day and it was amusing that Miss Bailey and Miss Anderson were feeling the pace, admitting they hadn't cum so often in a day in quite a while. The four of us eventually parted for the evening, the other two heading for the guest room to share a bed while Miss Rodriguez took me by the hand to her bedroom.

Shutting the door, we came together and kissed as I helped her disrobe so she was naked. Lying back on the bed, we lubed her cock together before I straddled her body and slid down her cock, leaning forward so I could kiss her.

"Ride me, sweetie. I've dreamed about you just riding my big cock for hours. We'll go to sleep after I've cum in you."

Though I loved riding her, I already preferred being on my back with Miss Rodriguez above me, her gorgeous eyes gazing down into mine, her beautiful body completely dominating mine, her big cock sliding in and out of me. My legs were spread wide to start before I had them wrapped around me. Miss Rodriguez was taking it nice and slow before I was basically begging her to fuck me. She still worried about hurting me, assuring her I was a big boy and I could handle it, but I really wanted her to cum in me before we went to sleep.

When she did finally cum inside me, the kiss we shared during her orgasm was the most intense of the day and night so far. Finally coming up for air, the look in her eyes no doubt matched how I was looking at her.

"We have to be careful, Stevie," she whispered, "But I can see how you feel about me already."

"And you feel the same, Miss."

"I've been hurt before but I'm feeling ready to open my heart, maybe take a chance, even with someone so young..."

She was still hard, and after stroking her back to life, I wanted her to take me from behind and properly fuck me for the first time. Resting on my hands and knees, I glanced back and smiled, wiggling my arse, as one of her hands ended up on my hip as she easily slid her cock back inside me.

"Fuck me, Miss," I moaned, "Fuck me hard."

"Are you sure, sweetie?"

"It hurt a little bit before, but the joy and pleasure far outweighed any lingering pain. And I want you to really enjoy yourself this time. Pound away, and when you need to, just mount and fuck me."

She had to almost carry me to the bathroom an hour or so later as my legs were like jelly but nothing could wipe the smile off my face. Holding me up as we showered, I could see her concern so hugged her tightly and whispered how much I cared for her already. I knew it was quick, but I added that she was my first so would always be special to me.

But I also wouldn't deny that I'd been attracted to her from the first moment I'd walked into her classroom. I might have been living out a fantasy, but I also knew how I felt.

Holding me in her arms after we'd dried off, she held me tight, and I think we both fell asleep rather quickly. I know I pretty much passed out as I was exhausted, and happy to admit I was feeling rather sore. Incredibly happy but a little sore.

Miss Rodriguez woke up before me, waking up to find me almost suckling at one of her breasts before I leaned back and smiled at her. "No sex today," she told me, "You need time to recover after we fucked you all afternoon and evening." She paused a moment, biting her bottom lip. "Did you enjoy it?" she asked softly, "No regrets in the morning?"

I replied by cuddling her and I think that was the real answer she wanted, feeling her squeeze me tightly in return.

Getting up to join Miss Anderson and Miss Bailey for breakfast, the three women wore gorgeous silk robes, that showed off plenty of cleavage and their long legs, giggling as hard cocks couldn't help themselves from making the occasional appearance. After we ate, Miss Rodriguez pulled me into her office so we could study for a couple of hours before lunch.

I didn't want to overstay my welcome, and I thought my sisters would at least be wondering where I was, so I told my three teachers that I'd head off home. Miss Anderson and Miss Bailey would head home at the same time, and I was a little disappointed having driven over the previous day, as I would have liked her to drive me home so we could have a few more minutes together.

After Miss Anderson and Miss Bailey drove off, Miss Rodriguez escorted me outside to my car. The last kiss we shared was one of lovers and people who already had a lot of affection for each other. Arriving home a little later, my father was home and barely asked where I'd been. My sisters showed a little more interest, and I think figured out pretty quickly that I'd been with a woman.

My oldest sister hugged me. "We're happy for you, Stevie," she said softly, "I hope we get to meet her one day."

Returning to school on Monday was a little weird as I had to behave normally. Miss Rodriguez also acted like nothing happened between us over the weekend, as did Miss Anderson and Miss Bailey. It was difficult for me, particularly with Miss Rodriguez, as my attraction to her was undeniable, and in those brief moments our eyes met, I knew she was feeling the same way.

By Wednesday, it was too much, and she called me to her office at the end of the day. Asking me to follow her to her house, as soon as we were inside, we were all over each other, and within ten minutes, we were naked on her bed, her cock buried inside me once again. I stayed as long as I could, making love as often as we could manage.

"Tash and Courtney will be a little jealous," she whispered after depositing her third load inside me.

"Miss... Out of everyone..."

"I know how you feel, Stevie. I don't want this to just be about sex, but it's difficult with you being my student, even if you are eighteen."

"How does this work, Miss? I love the sex already, but I want much more than that too."

"We'll figure it out, Stevie. The only question is... I can share you with others, but can you handle that?"

"Our first time was three of you with me and I loved it, Miss. If that's how we agree to go forward."

"Tash absolutely adores you, Stevie. I can't take you away from her. Courtney is a little bit more private. Then there are the other two teachers."

"Sounds like the world is my oyster."

"We're going to look after you in more ways than one, Stevie. That is something I can guarantee."

"So will I come around this weekend?"

"Make sure you bring a bag. And I'll be inviting Miss Chen and Miss Nguyen this time. Can you handle five of us?"

"I'll give it my best shot, Miss."

"Just what I wanted to hear." She hugged me tightly, feeling her cock press into my stomach as I rested my head against my chest. "There's only one other thing I'd love to hear sometime soon."

"Hearing that from me wouldn't scare you?"

"It wouldn't because I know how you feel already."

Walking me outside with the clocks close to midnight, we shared one last passionate kiss before I slid behind the wheel of my car. Opening my window, she leaned in and gave me one last kiss, her fingers sliding down my cheek.

"We're going to have a wonderful year together, Stevie."

"More than a year, Miss. I won't promise anything just yet, but I certainly don't want this to stop."

"You should go before I drag you back inside and just keep you to myself all the time."

"I'll see you at school tomorrow, Miss."

"Drive safely, Stevie."

Miss Anderson and Miss Bailey knew what happened and were not upset when I spoke to them the next day, admitting that they knew how I felt about Miss Rodriguez, but hoped we'd still have fun. I assured them that nothing was going to change too quickly, that we were having fun, and we would keep having fun for the time being.

"And this weekend is going to be even better," I added.

"Five girls. One man. Things dreams are made of?" Miss Anderson wondered.

"Fantasy becomes reality."

It was just the start of what would turn into a life changing year.