How I Lost My Hands' Virginity Ch. 01

Story Info
My first t-girl is a handful of woman.
1.9k words
4.35
77.8k
24
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Top18TS
Top18TS
13 Followers

Hey, boys! Just so you know, I'm not a writer, I'm a waitress/shot-girl, so please be kind with comments and suggestions. Thanks for reading, boys!

*

She opened the door to her dorm room and walked in, I followed behind her with my eyes glued on her tight little ass. She said it was cool if I crashed at her room after the party, and there was almost no way I could turn her down. I met her earlier that night, she was a gorgeous creature. She was 5'5" tall, with the figure of a venus, and her tits were an amazing 36 C, perfect shape and perfect size. Her ass was her best feature, not like a ghetto booty or anything, just small and round, like two little handfuls. Her hair was jet black, in one of those old school bob-cuts, and her eyes were the most subtle amber, the kind of eyes that could trap your own glance with theirs. Little did I know that there would be so much more to this goddess later on this night.

"Come on in, babe. I'm gonna go and put my PJs on...", she said before disappearing around a corner. The more I thought about it, the more I couldn't believe I was about experience such sexiness. Not that I was bad looking, myself. I stood at a decent 6'0", and I did go to the gym on a regular basis. I took a seat on her couch while I waited for her and looked around her room. While I was turned away she snuck back around the corner and sat down next to me on the couch, that's when I noticed her and I turned my head to see this beauty next to me, staring at me with those eyes, and smiling.

I looked down to see she was wearing a little white tank top, that was cut into a half shirt, with no bra, so I could see the shape of her tits through it. I then looked down further and noticed she was wearing a pair of briefs, and I always find it sexy when girls wear guys stuff. She was also still wearing her socks.

"Why don't you get out of those clothes, cutie, and get ready for bed, k?" I nodded, still awed by her body. I stood to go around the corner when she stopped me with a 'uh uh uh!'.

"What's wrong?" I said.

"Take them off right here, babe, c'mon! Gimme a lil strip show!" she said to me in a flirtatious manner. And I knew I couldn't refuse.

I first took off my shirt and tried to flex my muscles for her, she giggled and applauded my body playfully. Then I took off my pants for her and tossed them aside. I stood back up to see her give me a little 'spin around for me' gesture with her hand, so I did, and the whole time she just kept me in a sex trance with her smile. I went to go back to sit next to her when she stopped me again.

"Whao wait up babe! You're not gonna tease me like that are you!?" she asked, rhetorically.

"What do you mean?" I asked back.

She giggled and replied, "Why don't you get rid of those uncomfy boxers too!?" She said pointing at my boxers.

I was almost nervous to take them off because she had me so hard already, and I knew she would say something as soon as I took them off, but I didn't know what else to do, and she had a look on her face of curious impatience. I smiled at her and nervously laughed.

"Oh yea...haha...s..sorry..." I responded as I stepped back and pulled down my boxers to my ankles, stepping out of them. I tossed them aside as I stood up in front of her with my cock, hard as steel, bouncing in front of me. She started to giggle again.

"Hehe! Look at that! What a strong cock!" She said in a playfully seductive tone. "Why don't you help me take off my socks, cutie?" She asked as she lifted her foot towards me. I smiled and got down on my knees to help her take off her sock. As I tossed the first one aside I looked up and saw her staring down at me, grining as she told me "mmmm...you look so sexy down there!" At first I wasn't sure what she meant. Finally, throwing her second sock to the side, I went to stand back up when she leaned forward to stop me with a hand on my shoulder. "Easy, babe...why don't you stay down there for a lil while?"

I knew what she wanted and I was more than happy to oblige her request. Fallng back on my knees I reached forward to start pulling down her briefs. As my eyes traveled down her perfect body to her briefs, I noticed something a lil strange. It was a rather huge lump in the crotch of the briefs. I began tugging down her briefs when, to my complete disbelief and utter surprise, flopped out a cock bigger than I could ever imagine!

"Mmmm...that feels much better babe..." She sighed as her breifs slid down to her ankles and she kicked them aside. I just sat there on my knees in nervous shock until her sexy giggle brought me from my hypnosis. "Hehe...what's wrong, sweetie?", she asked.

"Uhhh...is that...like....real?!" I blurted out nervously, almost choking on my own question.

"Hehe! Well, why don't you touch it and find out?" She replied.

"Uhh...I dunno if I should...I mean...uhh...I never did before...", I just fumbled with words until she interupted me.

"Awww...shhhh! Don't worry babe, it won't bite! Hehe!" She smiled and opened her legs wider for me to move in closer. "Just touch it babe...why don't you see if you can fit your hand around it!?"

I shuffled in closer on my knees and got my first good look at what it really was. It was still soft, but her cock was insanely big. It was already at least 6 inches long, and thick as a soda can. I reached up to touch it. It was warm and fleshy, I pulled my hand back quickly at first, as if I touched fire, then tried again. I tried to fit my middle finger and thumb around her shaft. She giggled as my jaw must have dropped, "I...I can't do it..."

"Hehe! It's a lil more than you're used to, huh?!" She smiled as she reach forward to pet my head. "Are you nervous, babe?"

"Uhhh...yea...kinda...", I replied in a scared tone. Her cock was so much bigger than mine, bigger I thought a cock could be, and she wasn't even hard yet! On top of all this, I had no idea what to do, or if I even wanted to do anything with a cock.

"Ohhhh...it's ok, cutie. I'll be so gentle, and we'll go at your own pace, k?" She tried to comfort me, obviously realizing it was my first time ever trying this. "I'll teach you, babe. Try not to be scared, I'm always gentle when I break-in a first timer, k?"

I just nodded and swallowed hard.

"Good boy! First, try giving me a nice hand job... So, lift up my cock like this..." She instructed me as she angled her fat, floppy, and meaty cock upwards and positioned my hand on her oversized shaft. "...that's it, babe...do have a good grip?" I tried to hold it upright, but when she let go I felt how heavy it was as it flopped to one side. "Now stroke up and down, sweetie, go nice and slow at first..." In a daze, I did as she instructed, watching the beast in my hand flop over and almost out of my grip with each pump. It was hard to stroke her, I wanted to be gentle, but I had to hold her roughly or I'd lose my grasp. I couldn't believe what I was doing. I was on my knees in front of a monster cock, giving a hand job; but, at the same time, I was on my knees in front of a beautiful vixen, giving her pleasure. I was so confused, but so turned on, so scared, but so aroused.

"Mmmm..that's it babe...hehe..." She giggled as she watched me trying so hard to work her gigantic meat with my virgin hand. Unfortunately, my efforts were thwarted by my overly lacking experience, and her overly extensive size. "Why don't you try using both hands, babe?" I was so nervous, both from the magnitude of cock that I was trying to service, and the magnitude of beauty I was trying to impress. I never wanted to give a hand job before, or even touch another cock, but for some reason I felt like I had to please this...uhhh...girl? I put another hand on her fat shaft and continued to try and service her enormous dick.

It was a little easier with both hands, but I was still having trouble dealing with her girth. I looked down further and saw her two massive girl-balls hanging so low they were resting on the couch cushion. I was amazed at their size, also. Each one looked like a handful by itself. I was so shocked to recognize that this humongous arsenal of sex-weaponry was hanging off the hips of an angel. After about 10 minutes of her coaching my movements, and really working hard, I finally felt her meat starting to grow a lil. For some reason, I got really excited at the feeling of it. I was actually kind of, well, proud, I think, that I was able to please something so intimidating.

"It...it's growing, Tiffany!" I exclaimed.

She began giggling as I said this. I felt sort of embarrassed for being so excited, but she pet my head to comfort me. "Yep! Now you're doing babe...mmmm...now you're giving a hand job!"

I smiled back up to her, still kinda proud, and surprised of myself for being so. Then I looked back down and remembered the huge hunk of girl-meat that was flopping around in my soar hands. I felt the fear welling up in my tummy again as I felt the power swelling in her beast. Her cock was huge, and it was getting bigger, my hands and wrists were getting tired, and I was more nervous than ever now. I started to realize that if I couldn't work her over with my hands, she'd want me to work her over some other way, and I was not going to be some girl's bitch, even though she already had me on my knees...jerking HER off?

Her cock was barely semi-erect, and getting harder to hold onto with each pump, it had been about 20 minutes now and I could tell by the look on Tiff's face that it wasn't enough. "Mmmm...good job, sweetie...you ready for your next lesson, babe?"

I knew what she meant, and I wanted to please her, but I didn't want to try...anything else. I think I started tic a lil when I started to massage her cock harder, hoping she would reconsider, "but...I...".

She smiled down at me and stroked my hair to calm me down, "shhhh...sweetie, look at what you have in your lil hands right now...you did a good job, but I need more than hands, cutie. You want me teach you how to give me a nice blow job?" She told me smiling that cute smile.

As soon as I heard her say 'blow job' my mouth went dry, a fear rose in my gut, and all I could do was kneel there and barely nod.

Then...

...to be continued...

Top18TS
Top18TS
13 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
18 Comments
titans2138titans2138over 4 years ago

I wish there was a chapter 2 but it's been over 10 years so I won't hold my breath...

AnonymousAnonymousalmost 6 years ago
Waiting for next story

Waiting for next story please share fast

wolf9696wolf9696over 9 years ago
5/5

excellent buildup....dont stop now. Although, to make it just a teensy bit believable and thus, more enjoyable, try and keep the phallic proportions a tad bit realistic. Something that a TS lover COULD take down his throat.

AnonymousAnonymousalmost 10 years ago
loved it

Please continue

bambam4evrbambam4evrabout 11 years ago
Great start

I enjoyed the start of what has the potential to be a great series, I am looking forward to future additions.

Show More
Share this Story

Similar Stories

The Big Mature Shemale Next Door Little guy is fed cum and seduced.in Transgender & Crossdressers
Dickgirl Conquest Joe, unhappy with his girlfriend, meets a hot dickgirl.in Transgender & Crossdressers
A Surprising Landlady A new tenant gets an unexpected but welcome surprise.in Transgender & Crossdressers
His Teacher, The Transsexual A young man ends up very close to a teacher with a secret.in Transgender & Crossdressers
My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
More Stories