My mouth moved slowly up his shaft and I puckered my lips over the head of his penis.
I began to take deep, long pulls of his cock inside of my mouth. He moaned deeply and rocked his body in thrusts towards my mouth.
I was getting good at this. He was clearly enjoying it a lot.
My mind wandered to what it would be like if I was to suck men from now on instead of letting my girlfriend suck my little cock. The thought of all the men at the pool standing around me taking turns led to that now familiar feeling of tightening in my panties.
Gosh… I really was starting to like men.
The man let out an especially large moan, pulled my head back and said: “Slow down, little baby, you’re going to make me cum already…”
I stopped sucking, rested my head near his balls, and said: “I think we should go to the bedroom…”
A large smile wiped over his face. He was hungry to see how far I was about to go…
I lifted my body up and he followed suit. I held his cock as I walked him towards the bedroom, holding eye contact the entire time.
Then something strange happened as we got to the door of the bedroom. I suddenly got vocal, which I hadn’t expected myself to do:
“You like little sissy sluts, don’t you daddy?”
“Err… wow… yes… especially when they’re as cute and naughty as you are…”
I pulled at his cock which ushered him into the room. His face was partly shocked, partly thrilled.
I pushed him back onto the bed and he slumped down – looking back at me with a hungry look in his eyes.
I immediately began pulling his jeans down, wanting him to feel comfortable, but also wanting to have a fully naked man in the bed.
As soon as his jeans were low enough, I started to suck on his cock again. This time I moaned a little as I sucked like I had seen the girls in porn movies do.
It wasn’t long before he pushed my head back again and said the same thing:
“You’re too good at sucking… you’re going to make me cum so quickly…”
I sat up, not wanting the moment to end and began helping him out of his jeans and shirt.
“Take your clothes off too, sissy, show me that beautiful body of yours…”
I slid my skirt off with my back turned to him so he could see my ass open up as I bent over.
I looked back as I did it and noticed him immediately start to play with his cock. He was so turned on.
I climed back onto the bed, mounted him, and started to position myself comfortably on top of his groin. His hard cock pressed against the area between my balls and my asshole.
I started to grind slowly back and forth.
I felt his hands swirl around my body, grabbing the skin of my hips, rubbing my lower stomach, feeling the softness of my thighs.
He eventually reached one of his arms around my back, using it as leverage to pull me closer.
He began to lift his head from the pillow and puckered his lips for a kiss…
Our tongues danced across one another’s mouths, saliva building from the passion, my body grinding harder into his cock.
He used the hand behind my back to grab onto my hair. He tugged it back slowly but firmly.
My head rocked back and the feeling of slight pain made my cock harden a little.
He began licking and sucking my nipples. The harder he sucked the larger the nipples got until they looked like little tits. As I looked down at them, I pushed them together and said:
“You like my little titties?”
He nodded enthusiastically and laughed.
“You’re such a little slut.”
I felt his hand reach down to my panties and he began to tug on them.
They started falling over my buttocks.
“I want to pull off these panties and put my dick inside you…”
Those words gave me a sudden jolt. I had never been fucked before – it looked painful for the girls in porn films… What should I do? I asked myself…
It seemed as though my meetup with an older guy had taken far less time than expected.
Mr. Gregory was walking around our room, cleaning up, and tidying away our stray clothes.
In the meantime, I had begun fixing myself a drink. I needed something to calm the flood of nerves that were creeping up on me.
Before I could get myself fully relaxed, we heard a knock on the front door.
“Room service!”, exclaimed a voice from behind the door.
“Room service? Did you order anything?”, I asked Mr. Gregory.
“No, Skye, I have a feeling it might be our new friend. Go and check!”
I timidly walked over to the door, looked through the peephole, and immediately recognized the man on the other side. It was the man from Grindr.
I slowly opened the door, a smile plastered on my face for some reason. The light began to creep in the room from the otherside and the man started to look me up and down and smile.
“Hello, cute stuff. You going to let me in?”
“Hello, sir. Welcome to our room. This is Mr. Gregory my neighbor from back home.”
“Hey there!”, said the man, “Nice to meet you both and always happy to have an audience.”
I stood slightly away from the door so as to let the man walk through the door and into our room.
He took a quick glimpse around and then fixated back on me.
His eyes were moving up and down my body, taking in every inch of my young, slim frame.
He moved into the room.
“Do you want a drink or anything, sir?”, I asked.
“No, I’ll be fine, thank you. Where should I sit?”
“Err… Oh, here’s fine…”, I said as I gestured him towards the small sofa seat.
He slumped down into the seat, constantly fixing his eyes on me, smirking as if he had total control of what was to come.
I nervously wandered over to the couch, wondering what I should do or say. I was very new to encounters with men and I knew I must have looked very nervous and innocent.
“Here, have a seat on the arm of my chair here.”, said the man, tapping his hand on the chair.
I lifted myself onto the couch and put my feet on the empty space on his chair to balance.
I felt him shift his body lower so that his crotch began to rub against my ankle and foot. I could feel his pants tighten against my leg.
“You have a very pretty little outfit on you, don’t you sissy boy?”
“Err… thanks, sir. I’m actually wearing some of my mom’s clothes”, I chuckled nervously.
My mind immediately flashed to my stepdad. For a second I wondered what he was doing and how he was. I would usually send him a cute picture when I thought about him, but this time I would have to wait a little.
“Are you wearing a bra for me, sissy?”
“Yeah… It’s a matching set… panties and bra…”
“Well, isn’t that cute. Why don’t you show me?”
His hand tugged at my shirt and began to loosen the button that was covering my bra.
I soread my legs slightly to expose the matching panties that were slightly pulsing between my legs.
His eyes jolted down to the gap between my legs and he repositioned his legs and crotch as my legs moved.
He clearly wanted my foot on his crotch.
“I love these pretty little feet you have, boy, they’re so small and feminine, aren’t they?”
I giggled as his trousers tickled the soles of my feet.
“Erm, yes, sir, they’re quite small I guess…”
He grabbed both of them with his hands and began massaging them. I could see his pants begin to tent a little more while he play with my toes and soles.
He eventually positioned them both closely together in the center of his crotch and he started to gyrate his hips a little to get some friction.
At this point, I had started to feel more comfortable. The soft denim rubbing on my feet, his hands slowly stroking my legs, the plushness of the couch rubbing against my tucked private parts…
I took a moment to examine the room and realized how exposed I was on that couch. My chest was open, my panties on show, my legs spread. The windows to the room were open and any passer by could peer in and see us.
My crotch tightened. The thought of being seen was giving me a hit flush. Was I turned on? Holy shit, I was.
The man’s stroking continued and that feeling only intensified until I could hear myself moaning lightly each time his hands crept over my exposed thighs.
“You’re getting turned on aren’t you, sissy?”
“Erm… umm… err…”
“Kiss me, little one.”
I felt his hand move behind my back and gently pushed me closer to him.
I cradled his neck slightly so as not to fall too hard onto him.
I leaned in and felt his tongue dart sharply into my mouth.
I was taken aback and giggled. He pulled me in again and our lips met once more. I was more acclimatized this time and our lips danced along with our tongues in unison…
After a few minutes of making out, he pulled the back of my hair and moved my face slightly away from his.
“Get on your knees in front of me now, sissy.”
I was slightly taken aback, but I lifted myself off the couch and began to get on my knees in front of him.
He had already unfastened his jeans, and was struggling to pull them off his hips and thighs.
His large cock flopped out of his underwear right in front of my face.
“Now, boy, you know what to do…”
From what I had seen in porn, the woman usually starts to hold the penis and slowly jerk it up and down.
I did just that and the man let our a long deeo groan.
“Yes, that’s a good sissy. You like holding my big, daddy cock don’t you? You’re a little whore, aren’t you?”
I didn’t know what to say, so instead, I lowered my head towards his balls and started to lick them.
“Yeah, lick those balls you little sissy. You should worship those balls because they made the cum you so desperately need…”
I started to intermittently suck and lick his balls whilst rolling my hand up and down his shaft. His cock stiffened even more.
“Good, boy. Now lick my balls and rub your little hand over the head. Yeah, just like that you naughty little girl…”
“Now use that sissy tongue on your daddy’s head. Come on, little one, use your tong-“
He was cut off by how obedient I was. My tongue travelled all the way from his balls, up across his nine inch shaft, and up to the head.
“Oh yes, that’s a good little sissy slut. You know you’re role don’t you, bitch boy? Yeah, fucking lick that head.”
I though I had sent a Snapchat photo (Photo 1) to my current boyfriend – Matt, the captain of the football team – but it had accidentally gone to Mr. Grimshaw, my best friend’s father, who was also called Matt.
He politely replied to it after a couple of minutes: “Hey! I’m guessing that wasn’t for me haha – Looking good! I’ll see you later x”
I was really embarrassed, but what made matters worse was that I was having a sleepover with his daughter, Stass, later that day.
People thought Stass was my girlfriend because we spent so much time together but really she was just a great friend who was very happy to help me in my transition into a feminized bimbo.
When I got to their house, it was dinner time and of course the only seat left was next to Mr. Grimshaw. I said my hellos and sat down. He grinned at me.
We had a nice conversation about tomorrow’s weather – him and his wife were going to lie by their massive pool all day. It seemed as though the provocative Snap had been swept over.
Stass and I went up to her bedroom and whipped out all of her makeup bags and began trying out looks. It was something we loved to do.
The time ticked away and both of us were getting sleepy. We climbed into bed and started talking about boys. She told me about Danny who had fingered her in the back of her parents car when they were driving to the movie theatre. I told her that I was thinking about cutting it off with Matt and that I was looking for someone more … mature.
She joked that I should hook up with one of our friend’s parents – I laughed and brushed it off. I had already fucked a lot of the married men in the area and a lot of them are regular fuck buddies.
We eventually passed out and slept comfortably through the night. I was an early riser, Stass definitely wasn’t a morning person.
I went to check my phone and noticed Mr. Grimshaw had messaged me:
“Hey what are you guys doing?”
I sent him Photo 2. Stass was stirring but she went straight back to sleep shortly after I took it.
“Haha good! Thought she would be snoozing still. Weather is hot as expected. Pool it is!”
“Are you down there right now?”
He sent me Photo 3 and said “just getting ready!”
His big bulge was poking out of his shorts, catching me totally off guard. Did he mean to show me that? Was he flirting with me? I mean, I had been a family friend for so many years I had seen them all naked at some point but now I was legally fuckable, did he want to use that big pole on me?
“Err Mr. Grimshaw, I don’t think that was for me haha! We’re so bad at sending things I guess…”
“No it was for you! I was just showing you that we were still inside! Oh wait… could you see my.. thing?”
“Yeah haha. No worries Mr. Grimshaw… looks great! I’m down at the pool now anyway.”
I sent him Photo 4. Him and his wife came down to the pool and shouted “hey there!” across their massive pool. I waved back.
I noticed that both of them had gotten naked – pretty normal for them but I guess seeing Mr. Grimshaw in a new light had gotten to me. I just stared at his hot body and my little clitty began to get hard.
I got up to go inside – I needed to play with myself whilst I still had the image of him vividly in my mind. He gestured to me to grab the suncream when I came back outside. I took a sneaky video of him (Photo 5).
I went looking for the suncream and noticed how much it looked like a cock… I used some of the cream to lube my boy cunt and began to finger myself. As my hole got looser, I slid the whole tube inside. Then I got another message…
“Any luck with that suncream?”
I was so horny at this point I wasn’t thinking straight. I sent him Photo 6 – the suncream deep in my boy pussy.
“Oh wow… looks like you found it alright! God damn you’ve got me rather excited haha.”
He sent me Photo 7.
“Wow Mr. Grimshaw that looks massive!!!! Way bigger than this little tube! Bet it would destroy me haha”
“Yes it definitely would. It’s about the width of your arm haha.”
I sent him Photo 8 and wrote: “I noticed your wife went out shopping hope you don’t mind me using your bathroom to try on some of her dresses…”
“Not at all feel free. I’m just in our bedroom chilling. Come and show me your favorite outfit when you pick it!”
I walked out into the bedroom and lo and behold there he was on his bed. His massive, naked frame sprawled out.
I moved over to his bed giggling. I swirled around to show him my feminine body in his wife’s sexiest lingerie. He sat up and asked me if I knew how to do lap dances. Of course, I did.
He got up, sat on the chair near the bed and told me to strip for him.
I was eventually naked in front of him, his wife’s lingerie sprawled across the floor.
I climbed on top of him, shifted my body over his gigantic erection and started to grind on him.
His cock was sliding up and down my asscrack, becoming harder each stroke. Eventually, my lubed ass felt his cock pressing against my boy cunt. I slid myself down his shaft and started to ride him.
Getting over Mr. Manuela, or at least the times when I couldn’t be there in Barcelona with him, taking photos, fucking endlessly, was hard for me.
One of my friend’s father’s noticed how sad I had looked of late and consoled me a lot. He noticed, as the days rolled by, that I needed a getaway. He invited me on a fishing trip he was going to take alone that weekend.
I accepted, needing the break from home. I joined him at the local pier, and got aboard his new boat. It was medium sized, had two bedrooms, a bathroom and a small kitchen.
“You should get into your swim shorts – it’s going to get really hot out on the water.”, he said.
I hadn’t brought swim shorts, but I did bring my new bikini. I went downstairs to change, tucked away my sissy clit, put on denim shorts, and went up. As he steered us to the open ocean, I watched the land disappear away.
After 30 minutes, the boat stopped whirring. He came looking for me and was startled to see my smooth boy body in a sexy bikini.
“Wait… why are you wearing that?”, he asked.
“Oh I just feel more comfortable as a girl.”, I replied.
“Err… wow. Okay, then… Err… It looks good, I guess.”
“Thanks, Mr. Hillard, I’ve needed to hear that… I recently got back from Barcelona where I had been dating… a married man. We love each oth…”
Before I could finish, his hand grasped my butt.
“It’s ok, boy, this is a weekend where we forget our troubles… My wife’s been a pain in the neck and I just want to have a no-stress time.”
I nodded, walked to the front of the boat and began to sunbathe. He cracked open a beer and watched. I half-pretended I didn’t know he was watching. I unfastened my bikini top, then a few minutes later, my bottoms were off.
I strutted around the boat for a while naked, posing in positions that I thought might turn him on. He followed my suit, he’d taken off his shorts and was lying at the front of the boat, eyes closed, cock erect.
I walked over and put it in my mouth before he had noticed I was there.
He fucked me all over his boat, came on my face, and helped me forget Mr. Manuela for hours at a time.