The Making of an Angel Pt. 03

Story Info
My continuing story of my transformation.
1.7k words
4.49
14.5k
7
0

Part 3 of the 8 part series

Updated 06/09/2023
Created 07/23/2019
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

The making of an Angel part 3. All persons are over the age of 18.

***

On the drive home a myriad of thoughts were tumbling through my mind. I'm not gay but I could smell the stranger's cum on my breath and feel my panties teasing my puckered tight little hole. I was aware of my suspender clasps digging into my thighs and the feeling of the sheer nylons on my legs. My nipples throbbed where they had been pulled and tweaked. I knew this wouldn't be the end of it.

At every opportunity I wore panties instead of male underclothes and was in a constant state of near arousal. I couldn't concentrate and kept thinking about the humiliation of sucking cock. It consumed my every thought. I was starting to think of my cock as my clitty and my clitty needed rubbing. A lot!

I returned to the sex shop the following weekend wanting to look for a suitable dildo to train my tight little anus (or boi pussy as I now thought of it) to take a man. The lady smiled as I walked through the door.

"I had a feeling you'd be back honey," she said.

I blushed.

"How can I help?" She asked.

I hemmed and hawed and stammered out what I was looking for. She looked at me and walked over to the sex toy shelves.

"We have these" she said as she indicated a row of butt plugs.

They ranged from small to oh my god! The largest looked for all the world like a rugby ball.

"Who could fit that in themselves?" I wondered.

"What do you recommend?" I asked.

"You need to start off small" she advised. "Remember to use plenty of lube and some poppers to help you relax or you'll hurt yourself."

I picked up a medium Doc Johnson butt plug. The black contrasted nicely against my pale hand.

"Too big for a 1st plug" she said. "Try this one" and passed me a little purple plug.

It was about the length and girth of a man's middle finger. It was surprisingly rigid but flexible.

"I'll take it" I said.

I could feel butterflies in my tummy at the thought of putting it inside me.

"Use a good quality water based lube and some poppers" The lady finally advised.

I got home with my new purchases and decided to run a bath to relax myself in anticipation of my new experience. The water was nice and warm with some essential oils. My wife was out with some friends or more likely catting around so I gently washed my intimate regions before applying a large amount of lube to my middle finger. I stroked my pussy gently with my finger before sliding it in to the 1st knuckle. God! That felt good! My body tingled and I let out a small moan. Time stood still. I pushed my finger in deeper and felt it pass my muscle ring into my cavity. I slowly worked the lube into my pussy with my finger until I was nice and relaxed and very very wet. I pulled my finger out. It felt like something was missing. I felt empty without something in me. I reached for my rubber boyfriend and liberally smeared it in lube before kneeling in the bath. I took a deep sniff of the poppers. Wow! I felt hot. My heart was hammering in my chest. I gently pulled my butt cheeks apart as I slowly slid the rubber plug into my still virgin hole. I gasped as the plug stretched me until the point where it tapers back in. Once this was reached my pussy sucked the plug in greedily. It felt wonderful but I panicked that I wouldn't be able the pull my plug out. I calmed down and tried to relax. As I pulled the plug out it rubbed past my prostrate and I shuddered with lust. If I thought pulling my finger out left me bereft then I felt devastated when my new friend was removed!

After sliding my new toy in and out of my boi-pussy several times I found it was getting easier and easier. I didn't feel any discomfort and my new toy nestled nicely against my prostrate. I quickly came up with a plan...

Getting out of the bath I left my plug in and dried myself off. Bending over to dry my feet my plug shifted and I enjoyed the feeling. I wondered what walking would feel like and so naughtily decided to put on my wet look lingerie and black stockings and head to the local cruising ground. The temptation to rub my clitty was immense but I knew I'd lose all interest once I'd cum so I resolved to leave my clitty alone. I put my suspender belt on and bra. Next I slowly rolled a pair of sheer black stockings onto my legs. The feeling of the nylon was heavenly and bending over to fit my suspender clips to my stocking welts made my plug press against me in delightful ways. Finally I slide my panties on over my suspender straps ensuring my plug remained firmly in place. Feeling decadent I slid a condom into one of my stocking tops with a sachet of lube in the 2nd. Boy clothes over the top and I was ready to go!

I was aware of my plug in position all the way driving to the cottaging spot. It was an area well known for cock but I had no idea what to do. I got out of my car, locked it and walked up to the picnic benches. I looked around. Various men were wandering around so I sat down. About 5 minutes later a good looking trim guy walked up to me and asked if I was looking for cock. The true romantic! I said I was and followed him through the wooded area to an area which was obviously used a lot! Used condoms were scattered everywhere and my new lover was obviously well prepared as he had a blanket on the ground. A moment of panic suddenly seized me. What if someone saw us? I quickly realised I didn't care and if they wanted to watch I'd let them.

My new friend kissed me deeply and squeezed my bum. I was worried he might be sub or might not like trannys. I bit my lip as I slowly undid my belt and lowered my jeans. Judging by the hard-on in his trousers he didn't mind trannys! I shyly asked him if he like what he saw. He grunted yes then kissed me again before pushing me to my knees.

I opened my warm mouth like a good girl and started to slowly suck his cock. It was huge! I started to panic. Even with the slight stretching I'd had earlier and with my plug still in me there was no way I was going to fit this in me. As if reading my mind he brought me up off my knees and started kissing me again. He took the lube from my stocking top - god! That felt so slutty and reached around to pull my plug out with an audible plop. 1st one lubed finger was worked into me then a 2nd then finally a 3rd all the while he kissed me while I stroked his cock. When he decided I was lubed enough he took the condom from my other stocking top and passed it to me. I carefully opened the packet and rolled the thin rubber over his huge member. I actually caught myself licking my lips at the thought of what he was going to do to me. With a final kiss I turned around and sank to my knees on all fours. I pulled my butt cheeks apart and tried to relax. My lover positioned himself with his cock at my boi-pussy and started trying to push his fat cock into my virgin hole. I squealed at the pain but my clitty gave me away as it became swollen and hard. It felt like I was being split in two. He managed to get the head of his immense cock in past my muscle and suddenly he slid in. I honestly thought I was going to pass out. It hurt so much. My lover patiently waited for me to become used to his girth and length. As I did I found myself pulling forwards then pushing back onto his rigid member.

"Slut!" He hissed in my ear. "Cock sucking slut!"

I moaned at his abuse feeling every inch of his massive cock deep in my bowels. As I relaxed he started to speed up.

"Whore! Fucking tranny whore!" he snarled in my ear.

I whimpered with shame as this random stranger I had picked up fucked the masculinity out of me. I could feel his enormous erection pressing against my prostrate as he fucked me and I moaned like a bitch in heat. I couldn't take much more of this. My lover reached around and started pulling my nipples as I reached for my clitty.

"Leave it alone slut!" He commanded. "I need to finish in you".

His cock head seemed to swell like there was no tomorrow and suddenly I could feel him filling the condom inside my arse with scalding hot cum. It was too much for me to take and my clitty started spewing cum into my panties and onto my stockings. We both collapsed into a tangle of lust. My lover recovered first and pulled his softening cock out of my ravaged hole. I felt completely empty without a cock inside me. The used condom was dropped on the floor next to me. He turned me over and deeply kissed me before pulling up his trousers and leaving me there. After about 15 minutes I pulled myself together got dressed and stumbled back to my car like bambi. My legs felt like jelly. There were a few stares and sniggers. It was obvious what had happened to me and my new friend must have told some of the others that I was a tranny. I could feel myself going red as I got back to my car.

To be continued

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

Similar Stories

Feminizing First Step Ch. 01 A mother begins to feminize her son. First, a new swimsuit.in Transgender & Crossdressers
Briefs No. 01: An Unexpected Plug Two sisters go shopping.in Lesbian Sex
The Neighbor Daddy Next Door Daniel falls further into one older man's feminization trap.in Transgender & Crossdressers
After Church Crossdressing teen and the dirty old man.in Transgender & Crossdressers
Slow Descent into Sissy-Hood... Ch. 01 The beginning of a transformation into a sissy. Chapter 1.in Transgender & Crossdressers
More Stories