He really wanted to break my virginity… the thoughts rushing through my head were uncontrollable. I had never ever seen a guy naked until recently and all of a sudden I had given one a blowjob and, now, I was in bed with one.
I was nervous and scared about what was going on. I was away from my parents and the only two people here were older guys – horny, older guys.
Mr. Gregory was sat in a chair in the corner with a grin on his face and his hand rubbing the outside of his jean’s crotch.
He nodded to me enthusiastically. He wanted me to do it.
As I lay on the naked stranger, I reached down towards his hard cock. It was so hard. He looked up at my skinny, young body and was practically salivating.
I lifted my leg a little so that his cock could stand upright underneath me. It was big – how could that fit in me? It was at least as wide as my body.
He looked up at my face and said “go on little boy, do as you’re told, put it in that tight ass of yours…”
I moved my thong from my butthole onto one cheek so that my boy pussy was exposed. I let my body rock a little to feel his throbbing dick against the outside of my hole.
It felt good, a tingle inside.
I attempted to push my body weight onto it but I was just too tight. It wouldn’t go in even a little bit.
He started to get a little frustrated so he swung his arm around my back, lifted me, and lay me on the bed on my side. He was now kneeling over me with his cock positioning between my buttcheeks.
I couldn’t let him see how nervous I was. I looked away but, by doing so, was now looking directly at Mr. Gregory. He had a full smile and his pants were unzipped.
I felt the man push his cock harder against my boy pussy.
“Just a little push and we’ll be ready to go, little one…”
Fear had taken over. I was sweating. I was visibly uncomfortable.
He pushed even harder, this time forcing the tip of his cock inside of me.
After trying that for a while, he realized it wasn’t working.
“I need to use my whole body for this. Get on your stomach…”
I slowly flipped my body onto my stomach, my legs tucked under him, his body positioned right on top of me.
He pushed again.
Again, same problem. I was just too tight.
He grabbed at my shoulders for leverage. He yanked my body towards him.
I felt a little more of his cock slide into me. It hurt – I couldn’t do this.
I pushed at his arm with mine and tried to swing my body back upwards.
“What’s wrong, you little slut?”
“I-I-I can’t do this… not now… I need… I need to stop.”
He huffed and slumped off of me. He looked mad.
“Please sir, don’t be angry. I’ve never let anyone get this far. You’re very special. You-you… you’re so handsome and I like you…”
“Well let me make love to you then!”
“I can’t sir… If only I had practise with someone smaller before… I’m sorry…”
He rubbed his face. He couldn’t hide his frustration.
The sweat glistening off of his manly body was still such a turn on though. I reached for his cock and began stroking it up and down slowly at first.
He moved his hands from his eyes and looked back at me again. He still had some hunger left.
I moved my body so that my face was under him. I licked his balls, I licked slowly up his shaft, and I began to suck him again.
He was enjoying it. A relief for both of us. For some reason I really cared that he would be satisfied – it felt like my job.
He eventually rocked his head back and groaned. He gave me no forewarning as the cum bellowed out of his cock like a rocket.
My face was hit repeatedly by the splashes of his warm cum.
“Fuck yes… Ughhh…”, he moaned, “good fucking girl. Now lick it up…”
I did – I already was doing it – and I did it with a big smile on my face knowing I was his “good girl”.
Tune in for part 11 soon!
If you want to recap or read the other chapters for the first time – tap the “sissy thanksgiving” tag at the bottom of this post.
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.”
As I handed my phone to Mr. Gregory, I tried to remain calm. Grindr, huh? I guess it would be fun to see what guys say about me… I mean, I don’t need to hang out with any of them…
“Right, it’s downloaded, setting you up with an account… what should the bio say?”
“Err… I dunno… Straight guy, looking for friends?”
“Hmm… No, I’ll just put… Slender, smooth boi looking for handsome daddies.”
“Wait… what? No… I’m… wow… erm…”
“It’s fine, we can change it later. I’m going to set you as ‘Trans’ and say that you’re looking for ‘Right Now’…”
“Jeez, Mr. Gregory, I don’t know about all this to be honest…”
“Skye, listen, it’s just an app… it can’t hurt!”
“Sure, OK, Mr. Gregory, if you say so…”
“I need to take a picture for your profile…
I sat up in the bed, smiled, and heard the click of the phone camera.
“Perfect”, said Mr. Gregory, “Very cute, Skye… it’s uploading…”
I began to wonder what the world of Grindr was like. Do people make friends on there? Do older guys find nice, younger men to treat well and have conversations with?
I guess I was about to find out pretty soon.
“Has anyone messaged me yet?”, I asked.
“Actually, yes, Skye. I think you’ll like him. He’s only 260 feet away so he must be in the resort somewhere…”
“What did he say? What does he look like?”
“He said ‘Hi cute boi, aren’t you just adorable? What are you looking for?’… This is what he looks like…”
Mr. Gregory showed me the phone, which displayed a much older gentleman’s profile pic.
“Oh, he’s so old…”, I said.
“Yes, I think he’s just your type, Skye. A nice, mature guy will often be discrete and kind…”
“Err… OK… what did you reply?”
“I said ‘Hey sir, I am indeed adorable, but you haven’t seen anything yet ;)… I’m looking for someone to teach me stuff haha…’ … what do you think?”
“Wow that’s very forward, Mr. Gregory… are you sure I should be that forwar-“
“Oh now he’s asking to see what you’re wearing… Quick, go take a selfie in the mirror and show him your panties!”
I took the phone and without thinking I stolled over to the bathroom mirror, perched on the ledge, and took a selfie. I sent it directly to him.
“Wow! Nice! My wife thinks you’re right up my street!”, replied the man quickly.
“Your wife, sir?”
“Yes, my wife. We’re at the resort restaurant now eating lunch. She let’s me fool around with little sissies when I’ve been well behaved haha.”
“Sissies? What’s that?”
“You silly! You’re a cute lil’ sissy.”
I was confused. I took my time to think about what that could mean. It sounded insulting.
“Mr. Gregory… what’s a sissy?”
I could hear him chuckle and say: “Oh, Skye, that’s adorable. Why, you’re a sissy! A boy who likes to wear girl’s clothes, makeup, and shoes…”
“Oh, ok… That’s ok then…”
I looked back at my phone and the man had requested that I take my panties off and show him. He said that his wife insisted on me showing me naughty side.
I slipped my panties down my legs towards my ankles and took another selfie, making sure to hide my private parts as I leant over.
I hit send.
Seconds later he replied:
“Good! That’s a good little sissy! My wife is happy now. She said that you should not be shy and show us what what underneath those panties. Stand up straight so we can see your little member!”
I oblidged and stood upright. It took a couple of tries to make my penis look respectably big. It still wasn’t making me happy but I took the shot and sent it anyway…
He replied seconds later:
“Good boi! I love that cute body you have.”
I hadn’t heard that kind of feedback from a guy before – besides my stepdad.
“You really think so?”
“Yes, I think you’re fucking gorgeous!”
Wow. Someone thought I was gorgeous. I’d never heard that before. Something about reading those words fired me up…
“So what about you, sir? Why am I the only one sending photos!”
“Good point.”, he said “What do you think of this?”
“Holy shit! That thing’s massive compared to mine! It’s not even hard!”
“It’s not hard yet little one… but I intend for you to see it throbbing…”
“How big does it get?”
“It’ll be thicker than those skinny arms of yours!”
My heart skipped a beat. My groin started to warm up… Was I getting hard again?
“You still there, boi? My wife wants you to get on your bed and bend over…”
“I’m still here… umm… Ok, gimme a second.”
I went over to the bed and saw Mr. Gregory smiling.
“You’re getting into this aren’t you, Skye? And it’s only the first person you’ve spoken to!”
I laughed nervously.
“Yeah, I guess it’s kind fun… Will you take a photo for me?”
“Why, of course!”
I got on the bed and did my best downward dog. The camera clicked.
“Sent!”, said Mr. Gregory.
I looked at the picture and realized how suggestive it was. My loins started to swell again.
Moments later my phone buzzed.
“I told you that you’d see me throbbing…”
A picture followed. He was hard and beaming at the camera.
“Jeez, that thing’s massive.”
“Yes, and it does the trick for most bois… Want me to come over and show you?”
“Hmm.. maybe.. I don’t know, it’s kinda naughty.”
“Naughty is good. My wife wants you to take another photo like the last one but we want to see the other side… show us your butt ;)”
Nervously, I passed the phone to Mr. Gregory who, without a beat, took the phone and lined up the shot.
I lay down on the bed, kicked one of my legs up onto the pillow, bit my finger and looked back.
“That’s the best one yet, Skye. Awesome stuff!”
Mr. Gregory had already sent it. The photo was so revealing I was getting nervous that it could get leaked online. It was too late now, I had to either meet the guy and show him more or risk him being pissed off and showing the world…
“Thatta boi! I love that little pussy of yours. So does my wife. Which room are you in? I’m coming over after I pay the check…”
My heart started pounding. I began to sweat. Mr. Gregory noticed the change.
He took the phone and looked. I watched his face read and then smile.
He passed the phone back to me.
The last message was from me and it read: “Room 78”.
I tentatively laid my towel down on the level below where Mr. Gregory was lying. I was still a little nervous about the whole thing given that his towel was so exposing.
I knew that Mr. Gregory had seen me naked, I was OK with that, but seeing another man’s body was weird to me. I think my girlfriend would have been upset.
Either way, I let myself loose, calmed down, and laid down on the towel. I could tell Mr. Gregory was eyeing me, which made me even more uncomfortable.
I swiveled my hips away from him so that he could see my private parts. Partly because it would be weird if he was looking at it, partly because I was a little embarrassed about how small it was after seeing my stepdad’s picture.
“You should cover yourself in the sauna water”, said Mr. Gregory as he reached down and nudged my leg.
“Err… I don’t know, Mr. Gregory, I think I’m ok”
I looked away coyly as his hand lingered on my knee.
Then he reached down to my arm and said:
“Trust me, it will feel amazing, I do it all the time.”
As he said it, he pulled me up by my arm. I was now sitting upright, just below him.
“Just look how toned my arms are, Skye, that’s literally because I wash in the sauna after workouts, it really helps to lose the extra fat.”
Without realizing it, my arm reached out and started to feel his arms. They really were toned and, frankly, looked amazing for a man of his age.
“Oh, wow, great job, Mr. Gregory. They really are toned. Your wife must love them… my girlfriend sometimes tells me to do weight training. I think she likes the jocks.”
I tried to diffuse the tension with talk of our other halves. Mr. Gregory seemed to have nothing of it.
“Ah, forget about them. Life is about the here and now. You can make life whatever you want it to be.”
I felt him pull me closer as he reached for the water. I was a little unstable so I grabbed onto his shoulder for support.
We were much closer than I had anticipated.
As Mr. Gregory reached for the water, and began to pour it on me, my mind immediately started racing.
The sensation of the warm water, the steam coming off my body, my muscles relaxing… something happened that never had before.
I looked down at his towel as he was concentrating on pouring water over my shoulders and in my head I wanted to pull his towel down to see what was beneath it.
As the heat rose from the water, I was getting even more lightheaded. My loins began to girate, I let out little moans, and my thoughts kept developing…
What if I touched his… cock?
I had to slap myself in the face. What the fuck was wrong with me. Mr. Gregory is a man. So am I.
Mr. Grimshaw and I didn’t stop that day, we ended up fucking every single day of that summer. As the days rolled by, we got more and more daring.
I would come down to the kitchen in something skimpy early in the morning – the rest of the house would still be asleep.
He would hear me from his office, find me, and demand me to remove my clothes.
This particular day, I took a piece of clothing off every few steps as I moved towards the pool. By the time I was at the edge of the pool I was naked, on all floors, showing off my tight boy pussy to Mr. Grimshaw.
He was wacking off his cock furiously behind me – he was especially horny today.
I went over to the pool chair nearest to him, got on all fours and began to suck him. He gestured me to lie on my front so that he could watch more carefully as his cum gushed over my face. The hot streams covered my lower face and I quickly lapped all of his juice into my mouth.
He wasn’t finished.
He proceeded to fuck me in every position imaginable before cumming again all over my back.
When we were finished, we got into out clothes, and wandered back into the kitchen. Mrs. Grimshaw was in there in her workout clothes, headphones on, making a smoothie. If she had just looked out the window once she would’ve seen her husband nearly breaking me in two.
She noticed us eventually, pulled off her headphones, and started a conversation. She causally wiped something from my hair – her husband’s jizz – and told me that I had suncream down my legs.
She rubbed it in. Me and Mr. Grimshaw smiled to one another knowing that it was his cum flowing out of my boy cunt. Oof! Close call.