A Birthday Treat for a Virgin Sissy

As my birthday celebrations wrapped up, I said goodbye to my friends and got in my parents' car to drive home. I had just turned 19 and my friends had taken me out for dinner to celebrate. We had had a few laughs and a good meal, but secretly, I was desperate to get home.

I was a virgin at 19. Deep in the closet, I had been too afraid to try and meet a guy or date. I had decided that tonight, my 19th birthday, was the night I would lose my virginity. I was planning on downloading Grindr and finding the perfect guy for my first time. I was giddy with excitement and fear.

As I pulled into the laneway, I went inside. My parents were upstairs watching TV in bed. I knew they would be asleep soon, as it was already almost midnight. Heading downstairs to my basement bedroom, I pulled off my tight, light blue jeans, and got into my bed. Pulling out my phone, I opened the App Centre and found the app, clicking download.

Within a few seconds, the yellow and black icon had appeared on my home screen.

I opened it and started to fill out the profile.

Thankfully, I consider myself an attractive young guy. I'm somewhat short, at 5'7" and slender -- weighing in at just 135lbs. My brown hair is coifed into a faux hawk and I have green eyes that a few of my female friends have said are "cute". I liked to think so too...

I flipped through my phone and found a selfie that I thought showcased my face in a nice light. I also took a picture of me without my shirt on, hoping that my slender body might catch a guy's eye. I thought my ass looked pretty cute in my boxer briefs...

In the description section, I wrote out what I wanted:

"Young virgin looking for sweet, caring Daddy for first time"

I knew I wanted an older man for my first time. I had always been drawn to more mature men. I loved their masculinity and their confidence. Most of all, I really just wanted to be held by a man in his strong arms. I wanted to feel pretty and desired.

With my profile complete, I clicked on "Done" and was immediately taken to the page I wanted...

My phone was flooded with pictures of guys. Some handsome, some not, some young, some old. A little bit of everything.

I started flipping through the profiles, amazed at how many guys were close by in my suburban neighbourhood. Immediately I started getting messages. It seemed that an 19-year old virgin was a hot commodity...

I reached under my bed and pulled out a shoe box I had hidden under there. Reaching inside, I pulled out a dildo and a bottle of lube. These had been my only sexual solace for the past year as I imagined being with a man. I had bought them shortly after my 18th birthday. Wiggling out of my underwear, I squirted some lube on my finger and gently worked it into my tight hole. The dildo looked like a realistic cock -- about 6" with a reasonable girth. It was connected to a remote and had a vibrating feature. I turned it on and started rubbing it against my little bud. It felt so nice, gently pulsating against the hole. I felt my little cock getting hard at the feeling and I closed my eyes momentarily, imagining that it was a real man.

As my hole relaxed, I started to slide the dildo inside, feeling every inch slowly push inside my eager ass. My cock throbbed with pleasure. Finally, when the dildo was buried inside my tight butt, I turned up the vibration, wiped my hand with a tissue, and picked up my phone again.

There were at least 10 messages now. I flipped through them quickly. A few had no profile pictures, so I deleted their messages and moved on. A few of the guys were too young. One was an older man, but very overweight. But then, I opened one message and was delighted to see a truly handsome looking Daddy profile pic.

"Hey baby. I'd love to help you with your first time. What's your name sweetie?"

He was rugged looking, with a trim beard, crew cut brown hair, and piercing blue eyes. He was 51 but still very much in shape. In his second picture, he was shirtless at a cottage. Although he didn't have a rippling six-pack, he was well built, with a nice bit of a hair on his chest. I could imagine myself nestled up against that chest, feeling the hair brush against my smooth cheek as I nuzzled against him. I felt my cock throb at the thought...

My hands were trembling as I returned to his message and started to reply.

"Hiya :) I'm Evan. Nice to meet you! My gosh, you look super handsome lol."

I reached down and touched my cock lightly and readjusted the dildo still pulsating in my ass.

"Nice to meet you too Evan. I'm Steve. And you look very pretty! There's no way you're still a virgin looking that good?"

I blushed at the compliment.

"Aww, thanks. Ya, I've actually never been with a guy. I'm kinda still in the closet...But today is my birthday so I decided I really want to finally have my first time. Just want to find the right guy to share it with :)"

"Happy Birthday sweetie! Wow, still can't believe that you've never been with a man. But you're right to take things slow and find the right guy who will take care of you."

"Have you been with many guys?" I asked, pulling the dildo out my ass now that it had been well stretched.

"Yes and no", he replied, "I'm actually married, so I don't get to be with men as often. But my wife and daughter are out of town this weekend."

I felt a flutter in my chest...Married and a daddy-type? Super hot. But I was nervous about the idea of being with a married man.

"So you're hoping to have some fun while they're away I guess?"

"Well...hoping to find some cute young thing to share my bed with me while they're gone, ya," he answered. "What do you really want to try with a guy, if you don't mind me asking?"

"Honestly, everything!" I replied, letting my mind wander through my various fantasies. "I want to try giving a man a blow job, getting rimmed, frotting, and ideally getting fucked for the first time. Also, I know it's silly, but I want to try making out and cuddling too..."

"That's not silly at all", came the reply, "I love holding a young man in my arms and kissing him softly, rubbing my hands over his body. And, of course, the other things are also fun! Are you sure you want to try getting fucked on your first time?"

"Yes!!!" I typed back enthusiastically. "I've actually had a dildo in my ass while we've been chatting hehe! I love the feeling of having my ass filled up. But I really want to feel a real man inside of me."

"Wow, that's hot baby. I would love to be your first. I'll take it nice and slow."

A picture popped up in the chat box and I opened it. I was looking at the nicest cock I had ever seen. 7" with a beautiful curve and nice head. I felt myself drooling as I looked at it.

I realized that he'd probably want a picture from me too. I stood up and walked over to the mirror at my closet. Twisting my body and popping my ass out, I took a shot of my naked bubble butt. Nervously, I uploaded it and sent it to Steve.

"What a gorgeous bum sweetie," he replied almost immediately, "It's making me hard just looking at it"

I smiled with pride.

"Your cock is incredible! I would love to wrap my lips around it!" I replied eagerly.

"I bet you'd worship it so well baby. So what other fantasies do you have?"

"What do you mean?" I responded.

"Oh come on, you're an 19 year-old virgin. You must have tons of unfulfilled sexual fantasies. What really turns you on?"

"Umm, well I really want to try eating cum. And I'd love to take a shower with a guy. And, you know...other things lol."

"Other things like what? You can tell me anything"

I gulped, wondering if I could tell him my real fantasy. The conversation was going so well. And Steve seemed so perfect...I didn't want to ruin it by saying something that scared him off. But I did have a fantasy...one that I had had for some time.

"It's fine, it's probably too weird lol. I just want to be with a handsome guy like you :)" I replied.

"Don't be shy baby, you can tell me. What's your real fantasy?"

I paused, my heart racing. This was the first time I was really talking with a guy about my gay dreams. Was I really ready to talk about my deepest yearnings?

What the heck...it is my birthday.

"Well...umm...my big fantasy is to be feminized by an older man. Dressed up in girly clothes and fucked like a girl...I know, super weird :S"

My cock was rock hard at this point. I was absent-mindedly rubbing the tip as I waited for his reply.

"That's not weird at all. I'd love to make you my little girl."

I felt some precum dribble out of my cock as I read his reply.

"Really, you think that would be hot?"

"Ya, so hot! You're actually probably the same size as my daughter. I bet you'd fit into some of her clothes if wanted to dress up for me. I'd treat you like a proper girl."

My heart melted. I couldn't believe it. Here was a handsome man of my dreams who was willing to not only take my cherry but also fulfill my deepest fantasy.

"That would be amazing Steve! You've got me so turned on!"

"Me too baby. So what do you think, do you want to come over?"

My heart was racing as I considered the request. Every fiber of my being wanted to say yes. I wanted to rush over there and become this man's girl for the night. But the rational part of my brain was putting up red signs.

What if he didn't take it slow?

What if he had an std?

What if he took pictures of me dressed up and blackmailed me?

I bit my lip and squeezed my cock. After a moment of not replying, he messaged me again.

"I promise I'd take it slow with you and treat you special. And if you don't enjoy it, you can head home, no problem. I'd love to share this moment with you on your birthday, Evan."

"OK," I replied, putting my fears aside. "Send me your location."

The next half an hour was a blur. I wiped the excess lube off my ass and put my dildo and lube away. Standing up, I pulled my boxer briefs back on, my cock still rock hard. I bent over a few times trying to coax it down. Pulling my jeans back on, I checked myself in the mirror, fixing my hair.

Tiptoeing upstairs, I could see the lights out in my parents' room. I grabbed the keys from the hook I had left them on at the front door and quietly went outside. Starting the car, I plugged in my phone and looked at the blinking map in the message. Steve wasn't far, probably about a ten-minute drive. While I lived in a townhome, he was in a slightly wealthier part of the suburb. I knew it would be a long ten minutes...

Driving along, I tried to suppress the fears still flitting through my brain. I buried them under my excitement. I couldn't believe this was really happening! I couldn't believe I was finally going to be with a man! And I could feel the girlish yearnings that I had always felt inside me. The ones that had made me crank the Lady Gage on the radio. The ones that made me want to try ballet, instead of playing a sport. The ones that made me look at girl's outfits at school with envy rather than lust.

As I arrived at the right house, I pulled into the laneway. My heart was well and truly pounding in my chest now. My brain was screaming for me to turn around, but my little cock was rock hard. It was making the decisions.

"Hey Steve, I've just arrived," I typed into the app. Closing my phone, I walked up the front steps nervously and pressed the doorbell.

As I waited for it to open, I panicked, wondering if maybe I had gone to the wrong house. It was close to 1AM now and I was terrified that I might have just woken some poor family up. I started reaching into my pocket to double check the address when the door swung open.

"Hey Evan, come on in," Steve said, holding the door for me.

"Hi," was all I could muster as I skittered into the house past Steve, turning around to look at my host.

He didn't disappoint in real life. Standing 6', he had broad shoulder and nice arms. His face was dangerously handsome. And as I passed him, I could smell a feint hint of cologne. It gave him a very masculine musk. He was wearing darker jeans and a brown shirt.

"You look nervous sweetie. Don't be. We're going to have an amazing night together. I'm going to take good care of you," he said, reassuringly, reaching over to put a hand on my shoulder.

I looked up at him. He was smiling at me, and his eyes made me feel calm.

"You have a nice house," I replied, not knowing what else to say.

Steve laughed. "Ya, it's not bad eh. I own a small construction firm, so most of the house is custom built. Come on inside."

I bent over and took off my sneaker, glancing at Steve. As I hoped, he made sure to take a look at my ass through my tight pants. As I stood back up, he reached out and gave me his hand. I took it, feeling the warmth and strength of his fingers take hold of me. I loved the feeling.

He led me down the hall into the living room. He had a fire going and a hockey game playing on TV. Leading me to the couch, he sat down and invited me to sit next to him.

"So did you do anything else for your birthday?" he asked.

"Ya, I went out for dinner with some friends," I replied.

As I answered, he wrapped his arm around me, pulling in towards him.

"You are so adorable," he said, ignoring my response. "Let your body relax."

I did as I was told and relaxed, letting myself sink towards him. I turned my head, looking up at him, staring at those calming eyes.

Without warning, he leaned over and kissed me on the lips. It was so gentle but loving. I felt myself melt. His other hand reached over and gently caressed my inner thigh. My cock responded eagerly to the new feelings, swelling in my boxer briefs.

As I relaxed, I turned my body, wrapping my arms around his manly frame, feeling his gentle kisses on my lips. His hand that was around me, holding me close, gently caressed my shoulder. He pulled back from our kiss.

"You're a natural sweetie," he said.

I smiled and leaned back up, taking the lead this time.

I had read all about French kissing, and I knew what to do. I let me tongue slide out past my lips and his, brushing against his tongue.

The sensation was electric. He took back control, pulling me towards him and kissing me deeply, our tongues dancing around each other's. My cock was throbbing as we kissed, and I could feel some more precum leaking out. Sliding my own hand down his side, I felt around for his crotch. Sure enough, under his jeans I could feel something hard and big. I moaned a little as I felt it for the first time through the fabric.

Steve broke the kiss again.

"You are so sexy, Evan. But if we keep going I'm going to fuck you here and now, and that's not the plan. We need to get you ready for your big night. Make you feel pretty and girly, right?"

Biting my lip nervously, I nodded.

"Ok then, let's go upstairs. I've run you a nice bubble bath. There are lots of fruity soaps that you can use from my wife and daughter. Let's get you cleaned up and then we can go and help you pick out your outfit. Sound good sweetie?"

"Sounds amazing Steve!"

Taking me by the hand again, he led me upstairs and into their master suite. The king-size bed looked so inviting, and I couldn't wait for him to take me to it. But first, a nice relaxing bath.

The master ensuite was gorgeous, with a large double vanity, a walk-in shower, and a big soaker tub. As we stepped inside, I could see the bubbles in the bath. They smelled like strawberries.

"Why don't you get naked for me?" Steve suggested, letting go of my hand.

I looked around the bathroom nervously, then back at Steve. I could still feel my hard cock in my boxers, poking a tent in them.

"Get all those boy clothes off", Steve persisted.

I pulled my white t-shirt off, feeling it slide off my slender body. Unbuttoning my jeans, I unzipped them, feeling the hard cock prodding out. I wiggled out of my jeans, taking my socks off at the same time. Now, I was standing in front of this very sexy man in just my boxer briefs, with an erection clear as day underneath.

"Such a beautiful body," Steve said, running his hand over his crotch. I could see that he too was also still erect.

I pulled my boxers down and stepped free of them, now naked in Steve's bathroom.

"What do you think?" I asked, nervously.

"You are stunning!" he replied, moving forward toward me.

He put his hands on my shoulders, taking in my whole body. He reached down and gently took my hand.

"Give me a spin sweetie, let me see your beautiful ass."

I spun around giddily, making sure to show off my pert ass.

"Perfection," he smiled. "Climb into the tub and wash up. I want you to feel relaxed and pretty."

I climbed into the bubble bath, feeling the hot water relaxing me. The fresh berry smell was sweet in the air and made me feel carefree. As I sunk into the tub, I let the hot water envelope me, sinking beneath the bubbles. I let out a sigh of relief, feeling some of the nervousness and stress dissolve.

Steve walked over to the bathtub and sat on the ledge of the tub. He was still rubbing his cock gently through his jeans.

"You look so pretty in that tub. Way better than my wife," he said, reaching down to run his fingers through my hair.

He reached over and grabbed the luffa. Arrayed on the side of the tub were a whole assortment of fruity body washes, soaps, and shampoos. He picked a pink bottle and squirted some of the gel onto the scrubber.

Like a lover, he started to wash my body, letting me relax as he moved the luffa in circles, creating more suds and massaging my slender arms and torso. The body wash was fruity, like the bubbles, making me feel so feminine.

"That feels so nice Steve," I murmured, enjoying the sensations.

As he washed me with the luffa in one hand, his other hand slipped beneath the water, resting on my inner thigh. He rubbed it gently before letting his finger slide over to my erect penis. Gliding them over my smooth testies, he gradually took my cock in his hand.

I let out a moan of pleasure, my head spinning as I felt another man touch my private parts for the first time.

Steve stroked my cock tenderly as he washed my body, head to toe. I was in heaven. The sensations I was feeling were incredible. I felt so pampered. And the feeling of his hand around my cock was sensational. When he got to my ass, he told me to get on my hands and knees in the tub, ass in the air. He washed my bum with the luffa, then put it aside, letting his hands explore my ass. He massaged the cheeks and I purred with pleasure.

Then he slowly slid a finger into my hole.

My brain exploded from the feeling. I could feel every bit of his finger, every crevice of the skin, brushing against the cluster of nerves at my ass hole.

"Oh my god!" I gasped.

"Relax sweetie, I've got you," Steve replied, reassuringly, as he probed further with his wet finger, still slick with a bit of soap suds.

"That feels so amazing!" I said, fighting back tears of pleasure.

"Mmmm, I'm glad sweetie. I'm going to make you feel so amazing tonight when I take you in my bed."

As he probed my ass with his finger, I couldn't help but reach down between my legs and touch my cock. I rubbed with gently with my fingertips. It was slick and wet from the soap and water. I rubbed it like I'd seen girls rub their clitties, feeling so dirty yet perfect at the same time.

After a few minutes of this, Steve gently guided me back into a more comfortable seated position. He squirted some shampoo into his hand, and laid my head back into the warm water, getting it wet and then lovingly washing my hair. As he massaged my scalp, I started to imagine what was next...

When he was finished, I shook my head to loosen the moisture from my hair. Reaching into a jar next to the soaps, I pulled out a razor. Rubbing my legs with some buttery soap, I shaved each leg nice and smooth. I made sure to try and make a show of it for Steve, putting my legs up on the ledge as seductively as I could.