Category: sissy caption

Regular

Any of my femboy/crossdresser followers in the Bay Area?

Hit me up on direct message!

Hey all! Please help keep this blog alive! Y…

Hey all!

Please help keep this blog alive!

You can donate any amount anonymously on Patreon. From as little as $1, you can help keep the Secret Femboy’s slutty adventures going.

http://patreon.com/secretfemboy

If a lot of you donate, I will be able to release series like the Sissy Thanksgiving more frequently. I have a ton of other great series in the works after that one finishes!

Thank you for helping:

http://patreon.com/secretfemboy

Regular

Sissy Thanksgiving Pt. 8

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.”

He groaned as my tongue slipped around his head.

“Be a good fucking slut and suck that head…”

Tune in soon for part 9…

Regular

Sissy Thanksgiving Pt. 7

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.

*Click*

“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 guess I was going to meet him…

Tune in for part 8 soon…

Regular

Sissy Thanksgiving Pt. 4

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.

Stop. I said to myself.

“Are you ok?”, Mr. Gregory said.

“Err… yes… umm… no… actually it’s fine, don’t worry.”

He smiled, grunted, and continued pouring water down my back, my legs, and feet.

My mind wandered again.

Part of my brain was saying: “you want to taste his big, manly cock, don’t you?”

I began to think of it. Never had I thought of another man’s cock, let alone putting it in my mouth.

The visual started to form…

The thought of Mr. Gregory’s face contorting in pleasure made my little cock tingle.

What the fuck was happening.

I bet I could look so pretty and girly doing it.

Fuck. No. Stop.

The visual formed again.

At this point, my cock was hard. It was dribbling. I was so turned on.

“Err, lad, you’re err… liking this a little too much I think.”

I snapped out of my daydream, looked down at my crotch, and was mortified.

He knew it.

I wrapped my towel around myself quickly, stepped up, and said:

“I’m so sorry, I don’t know what’s happening.”

I ran out of the sauna.

Tune in for part four…

Free sissy story with me on messenger! Hit me up on messenger….

Free sissy story with me on messenger!

Hit me up on messenger.

Send me your Mr. Name (e.g. Mr. Hammond).

Explain your fantasy.

We will trade pics and describe the story.

You won’t be disappointed at all!

Let’s gooo!

Mr. Grimshaw and I didn’t stop that day, we ended up…

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.

Mr. Grimshaw and I didn’t stop that day, we ended up…

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.

This was a very efficient selfie trap session even by my…

This was a very efficient selfie trap session even by my standards! Mr. Garth was on vacation at the same resort as me with his wife, her sister and husband, and all of their 6 kids.

I met him in the pool where there was a bar. We had drinks and the conversation loosened up fast.

I told him that I was really into makeup and cosmetics – he told me how his wife never wears any anymore.

I told him I do tutorials for them – he told me to give him my number so I could send them. He told me he would show his wife, which bummed me out a little, but I agreed anyway.

Later that day, I sent him photo 1.

“Hey you! Cool meeting you earlier. Good fun 😉 here’s my latest makeup look.”

“Damn, girl, that’s amazing! Wish my wife knew how to do that…”

I got annoyed again that he kept bringing up his wife but after 30 minutes, he had sent me photo 2.

“At the beach if you wanna join x”

I replied with photo 3 a couple of minutes later.

“Ah, sorry, would’ve loved to pick up from where we left but I’m at the spa…”

“It’s cool, my and my wife left and went back to the villa x”

Again, talking about his wife. It really got to me. But out of the blue, the mood shifted. He sent photo 4. His hunky body completed naked, his hand covering only half of his thick cock.

“Omg. Mr. Garth! I think you meant to send that to your wife!”

“No. I meant to send it to this cute girl I met at the bar…”

“Me? But I’m a boy…”

“Yeah, but you’ve got the body of a horny little slut.”

I sent him photo 5.

“What this old thing?”

He immediately sent back photo 6.

“Yeah! It would look great on this…”

“You’ve got my little boyclit so hard Mr. Garth…” sending him photo 7.

“Lol it’s so small compared to mine… you’re so skinny I feel like I would break you…” he sent photo 8.

I sent back photo 9. “I’m pretty sure it would break me!! I like being broken. It almost looks too big for my mouth but I’m an expert at deepthroat lol”

“Come over. The family went on a trip. Room 34.”

I walked over immediately not realizing that under my mini dress I hadn’t worn any panties. The other men in the resort ogled at me as I hurried to room 34.

He was waiting at the door naked, swung it open, and ushered me inside.

I walked straight over to the bed, got on my hands and knees. My boy pussy was quivering at the thought of what he was going to do with that monster cock of his.

He grabbed my hips, pulled me close, and proceeded to completely destroy me.

When you notice the plumber doesn’t care if you are a boy…

When you notice the plumber doesn’t care if you are a boy with a little clitty and wants to get his dick sucked, fuck your boy cunt, and cum all over your mouth… It’s a heavenly day.

Categories