Category: sissy boi


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

Hit me up on direct message!


- Send me your Mr. Name (e.g. Mr. White)
- This is a fictional story and will last a while (we will send pics back and forth that get naughtier and naughtier)
- You will send me your “scenario” (e.g. I am your babysitter, I am your neighbor, etc)
- You will be playing 45 years old or over
- You will send me the age you want me to play (anything goes)

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.

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:


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…


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.


“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…

Please reblog my latest story posts (Sissy Tha…

Please reblog my latest story posts (Sissy Thanksgiving Pt. 1-4) and I might let one of the characters use my boy pussy eventually…


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…

Direct message me for a “text message” story b…

Direct message me for a “text message” story between you and my stepdad.

He will be your close friend / old buddy who has been living with his new wife for a year or so. I will be his stepson.

You will witness through his eyes (camera) my feminization and him finding out that I have been getting close to one of your other friends.

Message me with your name and be prepared to reply fast as these stories take a long time to get to the juicy parts.

Christmas day had arrived! I was up very early, unable to…

Christmas day had arrived! I was up very early, unable to contain my excitement. I walked downstairs to look at all the presents under the tree, a glorious site.

As I was shaking my presents to get an idea for what they were, I noticed a light turn on in the kitchen. I also noticed that Mr. Jenkins hadn’t actually put the makeup box and panties away last night, and there was also a little elf costume near them.

I peered into the kitchen and saw Mr. Jenkins fixing a glass of milk. I quickly took the panties, makeup, and elf costume and ran to the bathroom. I put them all on as I had the previous night and wandered back into the living room.

“Hey Mr. Jenkins! Merry Christmas!”

“Merry Chris… oh dear, why are you wearing that?”

“Because I figured no-one would be awake for a couple of hours and I wanted another one of my presents now!”

“Err… sheesh… I thought we agreed no-one would know about last night, someone might come down and see…”

As he said that, I started to slip off the clothes until I was down to the socks and thong. I slowly pushed the panties down my legs, making sure to keep eye contact with him. He shifted uncomfortably on the couch.

Once I was naked, I pulled a candy cane from the tree, lay on my back, and began to slide it into you ass.

“Look! Mr. Jenkins! I’m doing what Santa said to do.”

He looked like he was trying to compose himself. He jostled with his underwear. He then got up and said:

“Put the elf costume back on and go to the spare bedroom. Santa will meet you in there to tell you if you can have another gift early.”

I did as I was told – I was thrilled that I might get another present!

I walked up to the spare bedroom, right next to Mr. and Mrs. Jenkin’s room.

I lay on the bed for a while and then heard the door creek open, it closed, and then the lock shut.

“Ho ho ho, Merry Christmas young man!”

“Oh hey Santa!”

Santa towered over me on the bed and began to give me instructions.

“Now I want you to get on all fours young lad, and put your head down on the bed…”

I did as I was told.

“Now please remove those silly, little knickers – you won’t be needing them anymore ho ho ho…”

I slipped them down and rested my head on the bed with my butt up in the air.

“Now, remember you removed a present from inside you last night? Well, this time I will help you get it myself!”

I felt something brush against my exposed butt, maybe a hand or something.

As expected, I felt it reaching into my asshole, it felt too big for a finger…

“Santa, shouldn’t you only put one finger in first?”

“Ho ho ho, I think you’re capable of speeding things up boy!”

His hand, or whatever it was, pushed further inside of me. I winced and let out a little squeal.

“Shush now, boy… you don’t want to wake anyone up do you?”

I covered my mouth as his hand pushed even further in. He grabbed my hair to pull me closer towards him, then my chin.

He was very deep inside of me, searching for my next gift. It took him nearly 20 minutes of pushing his hand in and out before he said:

“Boy, turn around, I think you need some of my Christmas potion to get this present.”

I flipped onto my back and he pushed my legs back towards my shoulders, he then put what looked like his thingy towards my face.

“Now, boy, I want you to taste this candy cane and after a short while you will get my potion…”

I started to suck his strangely shaped candy cane and, lo and behold, minutes later, a thick Christmas potion landed on my face and mouth.

“Ho ho ho! Well done boy! Now go downstairs and pick one of your presents and bring it up here so we can unwrap it together!”

I was so thrilled that I ran downstairs without putting on any clothes. Mrs. Jenkins was alarmed and told me to go up and change. I grabbed a present, ran up to the spare room, and wrapped myself in Santa’s arms.

What a great man he is!

PART SIX Mr. Manuela’s thick, hard cock flapped out of…


Mr. Manuela’s thick, hard cock flapped out of his jeans and I hungrily grabbed it.

“Good boy.”, he said.

I sucked him long and slow, savoring the taste that I had missed so deeply while I was away from him.

I sat up, and put his cock between my ass cheeks, grinding up and down on it while I looked him deep in the eyes.

“Mr. Manuela, I’ve dreamt of your cock every night since I left… I’ve needed it… I wanted to feel it deep inside me… your cum so deep inside me… I want you to make love to me right now.”

He flipped me onto my back, stood up on the floor, and pulled me towards him.

For what felt like eternity, he rubbed his throbbing head around my boy pussy. He was teasing me, making me wait for something I had been dying to have inside of me.

“Please, Mr. Manuela, I’m begging you… I need you inside me… as deep as you can go…”

He wouldn’t give me what I was begging for. He was making me so horny that my little clitty was about to explode.

I reached down and held his shaft, moving it towards my hole. I felt the tip move in, then he thrust inside.

The only word to describe it was heaven. My love, Mr. Manuela, was finally inside of my boy pussy again.

We had sex for the whole evening – every position, every dirty word, every little scenario we could play out.

I needed that night so badly and I fell asleep in his arms in absolute bliss, his cum trickling out of my boy cunt. I was home.