Tales of Transwomen Tops Ch. 06

"Stop teasing," Miss Rodriguez warned, "Tash, you go get changed as well. I'll change after you two."

We heard the pair giggling away as they were getting changed in the guest room. Returning in a pair of bikinis, well with bikini tops as they had a sarong each around their waist. Miss Rodriguez took my hand, leading me towards the office, where I collected my bag. Stopping outside the guest bedroom, she gripped my hand tighter and slowly led me towards her bedroom. Shutting the door, she turned and pressed me back against the door.

"You're going to learn a few things in the next few minutes, sweetie," she whispered, her hand moving to caress my cheek again, "Please don't hate me for it."

"I could never hate you, Josie..."

"Thank you, sweetie. Mind getting changed together?"

"No. But I am... You know..."

"Sweetie, if you weren't hard, I'd be disappointed."

I blushed but also giggled as she turned and walked away towards one of the chest of drawers, watching as she searched and eventually found one hell of a tiny bikini. I couldn't take my eyes off her as she undid a couple of buttons of her sundress, letting that fall down her body to pool around her ankles. My cheeks grew warm as she wasn't wearing a bra and it was obvious her breasts were fake.

She turned around when lowering her panties, getting a fantastic view of her arse, watching her slowly turn around, her eyes only searching for my face as I looked her up and down. Gazing down at her hands, she slowly moved them away to reveal... a long, thick and half-hard cock.

"Please don't be afraid, sweetie..."

"That's so hot," I murmured.

I think my immediate response caught her by surprise. "You mean that, sweetie?"

Somehow, I managed to move closer towards her as she turned her body, watching her cock throbbing as it quickly got harder and harder, her chest rising and falling rapidly from her obvious excitement. "I mean, I had no idea, Josie, but I'll admit I often fantasise about beautiful women having either a pussy or a cock. I'm a very open-minded young man, or so I like to think."

Smiling at me, she started to put on her bikini as I undressed. Dropping my shorts and underwear, she stopped me once I was naked. I was rock hard as she pressed her body into mine, feeling her soft hands run up and down my back. "You're absolutely adorable, Stevie," she whispered, "And you have a very cute cock. Does it worry you I'm so much bigger?"

"No, Miss," I whispered, "It actually turns me on even more."

"Ah... So you like women with big fat cocks?"

"My fantasy was always a tall, strong woman who would be the aggressor, take the lead and, if she was interested, she could just... um...."

"Pound you into the mattress every night?"

"I know it might seem gay to so many people, but you're a woman, Miss..."

She hugged me tightly. "Thank you for saying that, sweetie," she whispered, "I had a good feeling about you, the moment you walked into my classroom the first time."

Sliding on my swimming shorts, we grabbed some towels on the way before stopping in the kitchen to grab drinks and a platter of snacks, heading outside to where Miss Anderson and Miss Bailey were already lying back on a sunlounge. Their skin was already glistening, so I assumed they'd already applied cream and maybe suntan oil.

"Lie down, sweetie," Miss Rodriguez told me, "I'll put some cream on your back, so you don't burn."

Lying on my front, she sat just below my arse. Knowing she had a cock, I giggled when the cold cream landed on my back before she started to rub it in. Feeling her shuffle slightly, there was no missing when her thick cock pressed between my cheeks, unable to stop the light moan that escaped me, but when I pushed back against her, her fingers dug into my shoulders a little harder.

"Roll over, sweetie," she whispered.

Lifting herself back, I smiled at the enormous tent that was already in her bikini bottoms. "He knows?" Miss Anderson asked.

"He does and he doesn't care, Tash," Miss Rodriguez replied, smiling at me. Leaning forward, she applied more cream before starting to rub it in, "And he's got a lovely little hard on while his teacher looks after him."

Gazing into my eyes, the smile didn't leave her face as I felt her almost rubbing her cock against mine. "Can I touch it, Miss?" I whispered, glancing down to see the thick head and an inch or two poking out from the top.

"I'd love you to touch me, sweetie," she whispered back.

Reaching down underneath her, I gently ran my thumb over the head of her cock, causing her to hiss as it was already slick her pre-cum, before I reached down further and gently grasped a couple of inches in my fingers. "Fuck it," she muttered, undoing the ties of her bikini top, freeing her breasts again.

"I guess we're not wasting time now?" Miss Anderson asked.

"Show him, girls. He won't mind." Then she leaned down and kissed me. I whimpered immediately as I gripped her cock tighter, earning a soft moan as her tongue slid into my mouth rather quickly. I moaned softly as I stroked her cock a few times, earning a soft moan from her in return. Breaking the kiss, she sat up and I moved with her, not wanting to release her cock. Smiling at me, she undid the ties of her bikini bottoms to free her cock completely.

"Did you bring lube out?" she asked.

"Of course we did," Miss Bailey replied, "Is he ready for this, Josie?"

"Sweetie," Miss Rodriguez said softly, again caressing my cheek, "Look at my two colleagues."

Having been so focused on Miss Rodriguez, I turned to see the other two teachers were now sitting side by side next to the sunlounge I was on. Both were naked, a pair of nice fake breasts on each chest and a big, thick cock between their legs. I couldn't help smiling as Miss Rodriguez giggled. "His cock just got a little bit harder, girls," she said, "Sweetie... Would you like to pleasure the three of us? We know you've never been with anyone. We'd love to be your teachers in more ways than one."

"You would?"

"We think you're absolutely adorable, Stevie," Miss Anderson replied, "Yes, you're new so I guess that also helps, but we usually take one young man under our wing each year. Unfortunately, we haven't found a young man who wants to stay with us after the year together..."

"The three of you want me?" I had to ask.

"Us three plus Miss Chen and Miss Nguyen. They're just like us and we know they both really like you too," Miss Bailey replied, "They would have come this weekend but thought we shouldn't overwhelm you too soon."

"What would you like to do, sweetie?" Miss Rodriguez asked.

"I'd love to suck your cock, Miss."

She leaned down and kissed me again, pulling me tight to her body. Moving down to her breasts, I had to give them some attention, making her moan rather quickly after I'd latched on and started to suck, my hand moving its way between her legs to slowly stroke her cock. While I was busy with her, I sensed a presence behind me and the feeling of a thick cock pressing against my lower back.

"Suck her tits, sweetie," Miss Anderson whispered into my ear, "Then get ready to suck her big cock. Will you swallow her thick, delicious cum?" Nodding as I suckled, I sensed her smiling. "Good boy. And we cum a lot, sweetie. We'll fill your mouth first, and when we make love..."

"Thank you for saying we'll make love to him, Tash," Miss Rodriguez moaned.

"We want him to enjoy this, Josie. We're always gentle when breaking them in. Once he's used to us..."

Moving from breast to breast, her fingers ran through my hair, showering me with compliments, before she lifted my head away to kiss me again. Quickly repositioning, she sat back after ensuring she was sat up, spreading her legs so I could kneel between them, gently grasping the base of her thick cock, her large balls hanging between them. Glancing back, Miss Anderson and Miss Bailey were behind me, their hands immediately caressing my arse. I was smooth all over my body and I think they were enjoying that aspect.

As I ran my tongue up and down her thick shaft, I felt a wet tongue run along each of my cheeks and I was left thinking I was going to have my arse eaten for the first time. Focusing on Miss Rodriguez, her fingers continued to caress the back of my head as I ran my tongue around the thick head of her cock, tasting her pre-cum, which continued to flow.

"That's it, sweetie," she whispered, "Time to swallow some of it. Girls, don't distract him too much. He'll suck you off afterwards, won't you, sweetie?"

"Only after I make you cum first, Miss."

"We're definitely keeping him," Miss Bailey said with a giggle.

Swallowing as much of her cock as possible, Miss Rodriguez released a moan of appreciation, only stopping when it hit the back of my throat. Hands continued to caress my body, feeling a cock being pressed between my cheeks to tease me, as my head bobbed up and down on her cock. Her fingers gently grabbed my hair as her hips started to move at the same time.

"I really want to lick his arse," Miss Anderson stated softly, "He's got a deliciously pink rosebud here, Josie."

"After he's blown you both, then we'll get him ready for us to make love to him." Gazing up into her eyes, she smiled down at me, "You like the sound of that, sweetie? The three of us taking turns inside you?"

Releasing her cock, I stroked it as I leaned up to kiss her. "Want me to stay the night?"

"Tash and Courtney were going to sleep in the guest room. You're staying in my bed tonight."

"I really want to make you cum, Miss."

"Then get those beautiful soft lips around my cock. I'm going to fill your mouth."

Smiling as I wrapped my lips around her cock, Miss Anderson and Miss Bailey moved so they were in my field of vision, sitting down and stroking their cocks at the same time. Bobbing faster and faster, I sealed my lips tightly and listened to how Miss Rodriguez was reacting but also what she told me to do.

Her hips moved again and when her hand was starting to keep me in place, I sensed she was probably getting close. "Fuck," she moaned.

"As soon as he's done, I need him to suck me too," Miss Anderson moaned.

"Maybe he can do us both together?" Miss Bailey wondered.

I was far too focused on Miss Rodriguez, watching her face, feeling her thick, hot cock in my mouth, throbbing with excitement. She moaned a couple more times, her fingers gripping my hair even tighter, and I knew she was now on the verge. Thankfully, she was polite enough to first warn me, then suggest the best way for me to take her cum, moving my lips back to just hold the head of her cock, using my tongue on the sensitive underside, using my hands to stroke the rest of her shaft and balls.

It all worked a charm as she exploded within a couple of minutes, thick, hot cum flooding my mouth. I savoured the taste before swallowing down each mouthful. I'm fairly sure I swallowed down at least half a dozen spurts before she simply dribbled the rest as I used my tongue to clean up her cock. Moving up and down her shaft, she lifted me up to kiss me, wrapping her arms around my body and pulling me tight.

"Thank you, baby. Thank you," she whispered, her hands moving down to my arse, feeling her tickle my rosebud.

"That was so hot, Miss."

"I'm glad you liked it, sweetie."

"I loved it. I've always wondered what it would be like to share something like this with a woman."

"He's dangerous, Josie," Miss Anderson said, "He's going to be far too sweet."

Moving off the sunlounge onto the ground, Miss Anderson offered her hand and led me over to the lawn, getting onto my knees and Miss Anderson and Miss Bailey offered their cocks for me to pleasure. I knew enough to suck on one and stroke the other, though Miss Rodriguez followed, suggesting they lie down so I could focus on them as she got me ready.

Feeling Miss Rodriguez start to lick my arse felt weird at first, but I loved having two cocks to pleasure at the same time. "Do you need to cum, sweetie?" she did ask me.

"I'll cum when we make love, Miss."

I eventually focused on Miss Anderson to make her cum as Miss Rodriguez enjoyed licking my arse, then applied lube. That caused me to stop and glance back, watching her smile as she told me what she was going to do. I managed to stay relaxed as a finger slid inside me, head bobbing up and down faster and faster on Miss Anderson's cock as Miss Rodriguez gently pumped her finger into me.

Miss Anderson was excited and came in my mouth within a few minutes, sitting up to share our first proper kiss, her hand gently stroking my cheek and the smile that formed on her face made her look very pretty. Moving over to Miss Bailey, I remained sitting on my knees as Miss Rodriguez wrapped an arm around my chest with two fingers now in my arse.

"Like it, baby?" Nodding as Miss Bailey held my head in place and gently thrust into my mouth, "Or do you love it?"

"He's loving it," Miss Anderson replied for me, "His little cock is so hard and dripping pre-cum."

"You need a big throbbing cock inside you, don't you, sweetie?" Miss Rodriguez breathed into my ear, "You want me first, then Miss Anderson and Miss Bailey to fill you up too? Maybe we'll invite Miss Chen and Miss Nguyen next weekend, the five of us just taking turns..."

Moaning around Miss Bailey's cock, I whimpered as I felt a third finger slide inside me, Miss Anderson moving closer and slowly stroking my cock at the same time. I moaned a couple of times as I didn't want to cum then and there. "Fuck, he's pretty good already," Miss Bailey groaned.

"I was turned on from watching him suck Josie for so long," Miss Anderson added, "Then again, her affection for him is already obvious."

"I'm taking him inside once you cum, Courtney," Miss Rodriguez told Miss Bailey, "We're making love on my comfortable bed."

Miss Bailey came a few minutes later, having got used to taking a thick cock in my mouth, having swallowed more of hers than the first two. Not quite into my throat but I had a feeling this was just the beginning on my education. After swallowing all her cum, Miss Rodriguez removed her fingers and stood up, offering her hand to help me up. Leaning down to kiss me, she smiled and whispered that she loved the taste of cum in my mouth. Cuddling her, I sighed as she wrapped her arms around me, with Miss Anderson hugging me from behind, feeling a pair of her fingers slide inside me.

"Fuck, he's tight," she whispered.

"We'll just be gentle, Tash," Miss Rodriguez whispered in reply.

"I really want to slide my cock inside him now."

"After Miss Rodriguez," I said softly.

"Of course, sweetie," Miss Anderson assured me, though her fingers continued to gently fuck me, "Do you like my fingers though?"

"I love them. Does Miss Bailey want a turn?"

She did, feeling Miss Anderson remove her fingers, Miss Bailey pressing into me as she slid two fingers inside me. Complimenting me on how tight I was, she gently stroked my cock at the same time as I leaned up to kiss Miss Rodriguez again.

"It's time," she finally announced, Miss Bailey removing her fingers as I was led back inside, not stopping until we arrived at the master bedroom. Letting me go, Miss Rodriguez told me to get on the bed and lie down, Miss Anderson and Miss Bailey getting on the bed with me, lying to either side, as Miss Rodriguez walked around to the foot of the bed, lubing up her cock as she smiled at me.

Getting me into position on my back, lifting my arse with a cushion, she spread my legs as her glistening cock swung, leaning forward and kissing me as I felt the head press against me. Whimpering into her mouth as she pressed forward, I groaned as the thick head of her cock slowly, ever so slowly, slid inside me. Resting my hands on her back, my fingers dug into her as she slowly slid more of her cock inside me.

"You're doing so well, sweetie," she whispered, kissing each of my cheeks, "Is it hurting?"

"No," I whimpered, "It feels so good, Miss."

"I'm glad, sweetie. Want some more of my big cock?"

"I want it all, Miss. This is what I fantasised about." Glancing left and right, I blushed, "Being in a room with beautiful women who had a big surprise for me between their legs."

Kissing me again, she kept pushing, feeling my arse slowly but surely accepting more and more of her cock until her balls gently tapped against me, looking down to see her entire length had disappeared. She smiled at me, kissing me again, before she slowly started to fuck me. Gripping her back, I held on and just savoured the feeling of her thick cock sliding in and out of me.

Glancing left and right, Miss Anderson and Miss Bailey stroked themselves to keep their cocks hard but kissed my cheek and whispered that I looked happier than anyone they'd been with before. Returning my attention to Miss Rodriguez, I moaned as she sank her cock a little harder and deeper, my fingers digging into her back again.

"Not hurting you, sweetie?"

"Keep going," I whimpered, "It feels so good, Miss Rodriguez."

"I do love the fact he keeps calling us by our names," Miss Bailey said, kissing my cheek, "I think we should keep that going."

"I'll call you whatever you want when you're inside me, Miss Bailey."

Miss Rodriguez moved my legs so they were now over her shoulders, starting to thrust faster and faster. When her fingers wrapped around my cock at the same time, I nearly exploded immediately, Miss Rodriguez smiling at the series of moans and whimpers that escaped me. Thrusting even faster, her hand pumped my cock, and I knew I was going to cum.

I barely had time to warn her before the first spurt erupted from my cock. "That's it, sweetie," Miss Rodriguez said softly, leaning down to kiss me again, "Cum with my big cock inside you."

"Please don't stop," I whimpered.

"We won't stop until you've had enough, sweetie. I promise."

Now that I'd cum, I could just concentre on Miss Rodriguez and her big cock inside me. She released my legs slightly, moving to spread them wider, which changed the angle of her fucking me. Meeting my eyes, I knew what she needed, gritting my teeth as she started to pump me faster and faster. Whispering for her to fuck me, she smiled and stroked my cheek as her other hand ended up on my arse as she was getting ready to cum.

When her cock started to throb and those first couple of spurts filled me up, I felt that warm sensation I'd often heard about when someone cums inside you. Her cock throbbed and throbbed, and she must have cum even harder, and even more, than when I'd blown her earlier. She kept thrusting until she needed to stop, leaving her cock buried deep as we shared a very soft kiss.

"We're definitely doing that again, Miss!" I stated enthusiastically.

"Later tonight when we're alone in bed... We'll make love until you can't keep going."

"And you can keep going, Miss?"

"The three of us can stay hard long after we've cum. And we all cum a lot each time."

Pulling out left me feeling empty and sad, though Miss Anderson moved quickly to sit between my legs, her cock lubed up and ready. She tapped my butt and made a gesture, rolling over and looking back over my shoulder as she pressed her cock against me. Miss Rodriguez sat in front of me, her cock still hard, glistening with cum and lube. I knew about arse to mouth, but I didn't think they'd expect that of me yet.

Miss Anderson ran a hand up my back to my shoulder and rather easily slid her big cock inside me, all three women of similar size. Far longer than mine and as thick as the largest cocks I'd seen in videos I'd watched in private. She buried her cock rather quickly that earned quite a grunt from me, but I assured her it didn't hurt.

"Take it easy, Tash," Miss Rodriguez warned her, "We don't want to hurt him. Remember?"

"I won't hurt him, but I just wanted to bury my cock inside him."