Snagged! Ch. 05

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I go out on my first real date with Chanel.
2.1k words
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Part 5 of the 5 part series

Updated 06/15/2023
Created 12/15/2022
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grgy56
grgy56
1,564 Followers

"Really?" I asked. "You would really like me to go out with you as Joan?"

"Yes, if you feel comfortable enough." Chanel confirmed. "I don't want you to feel any pressure but I'd love it if you did!"

After I revealed myself as a transvestite and Chanel revealed herself as a transsexual, we made out like rabbits. I can't tell you how many time she made me cum that night or how at ease I was with her when I woke up the next day in her arms but the fact she still wanted me made me feel so... wanted.

"We can go for an early dinner since we really missed breakfast and lunch. That way the restaurant won't be too busy. That is if you are worried about being seen." Chanel suggested. "Wear something pretty. And I'd love it if you wore stockings for me."

I left for my apartment across the hall. Of course I didn't have my key since the night before I was car jacked and my keys along with it. I turned back to Chanel's apartment where she was standing in the doorway with my keys dangling from her index finger. "Call me when you're ready to go!"

Inside my apartment, the first thing I did was call my insurance company to report the theft. They suggested I also get my locks changed if they had my keys. When said I still had all my ID's, they mentioned that they could trace my address via my licence plate. "Oh. I didn't think if that."

The call done, I needed a shower. I removed my forms and cleaned them before hopping into the shower. The hot water felt great as it pelted my body. The dirt from last night washed down the drain. I made sure that my mostly hairless body was still mostly hairless.

Cleaned and dried, I dusted myself with a bit of perfumed powder and paraded naked to my bedroom. I went to my closet and rummaged through it to pick out what I might wear for Chanel. "I think this will be nice."

I laid everything out on the bed. Then I replaced my forms on to my chest. Braless, the heavy forms pulled downwards but remained secure. If I really wanted to, I could go braless, but I just love wearing bras too much. I hooked on a pink and black satin, long line bra. It had six eyelets to hook in the back. The bottom stopped just below my ribs. Rather than the matching panties and feeling a little wicked, I slipped on some black lace, cheekie, boy panties. The garter belt matched my panties. I fished the eight dangling straps through the leg holes. I rolled up a new pair of nude seamed stockings and clipped them to the garters.

I redid my make-up, not too slutty but not too angelic either. The eye liner wasn't as thick as I would normally do it nor was my mascara. It was just enough to accentuate my eyes. Lipstick was a nice cherry red and looked great. I brushed out my hair and decided to leave it more natural.

The dress I opted for was a black and pink summer dress. It would match my bra very well. I slipped my arms into the dress and did up the bottom four of the five front buttons to show off my cleavage. It was a bit short stopping at mid-thigh but long enough to keep my stocking tops and garter clips hidden.

The shoes were some red strappies with five inch stiletto heels and an inch platform. I loved how I could show off and wriggle my red painted toes.

I attached some dangly earrings onto my ear lobes and a black ribbon choker around my neck. The front of the choker had a small white pearl accentuating it.

Finally I sprayed some Guerlain eau de parfum into the air and walked through the mist. One more check in the mirror with a bit of nervousness and I gave Chanel a call. "Okay. I'm ready!"

Almost immediately there was a knock on my door. Way before I could go to unlock it. When I opened the door, of course Chanel was standing there. She was nicely dressed in a vibrant red knee length front button dress, a matching wide brimmed hat and stiletto heels. She looked incredible. Her make-up was perfectly applied.

"Hi Joan. You look very nice." Complimented Chanel. She looked at my eyes. "I hope I don't offend you, can I give you a couple of make-up hints?"

"Oh no. I'm not offended. I really didn't learn from anyone other than from the net." I replied enthusiastically. "I tried my best but I didn't have any mentor."

"Oh, I mean... No, your make-up itself is very nice and proper but there are some extras that they never tell you about." Chanel told me as she reached into her purse. "I was the same as you but my friend Kate helped me out a lot."

Chanel had me sit down. She pulled out some liner and just extended my eye line a bit saying it will really makes your eyes pop. Then some lip gloss sealer to prevent unwanted smudges. She then applied a bit of blush to define and highlight my cheek bones. And then she kissed me on the lips. "It's smudge proof in case you need to give someone a blow job!"

I looked at myself in the mirror and was amazed how just a little more detail really made me look amazing. The gloss gave me puffy lips; in deed perfect for cock sucking. All I could say was. "Wow!"

We took her car. She retracted the roof so the warm sun was beaming down on us. She wore big, cat eye sunglasses, but I was squinting until she handed me a spare pair of sunglasses to put on. At a stop light, I peeked and saw some guy in a Lexus LX look down at us. I turned my head to him and smiled. I guess he was embarrassed at staring and immediately turned away.

Chanel parked in front of a small bistro. I got out of the car with thanks to Chanel making me feel much more confident and comfortable. The bistro had a small patio as well but without the protection that the car afforded, the weather wasn't conducive to sitting there. But we sat inside next to the open picture window. I almost felt on display.

The early dinner was great and matched with plenty of drinks. Many of them were bought for us by men who stopped there probably after their work was done. Being new to this, I followed Chanel's lead. Other than raising our glasses to thank them, we gave them no other notice. I wasn't sure if Chanel was doing it for my benefit or not.

During our time there, Chanel managed to slip her hand beneath the table. She undid the two lower buttons of my dress and stroked my stocking thigh. Every once in a while, her hand went higher and rubbed my hard cock. She even did it as we ate. I was very nervous at getting caught. In fact, Tiffany our server I am sure did catch us. She gave us a smile and left us be. And as such, I drank a lot of wine.

By the time we left, I was quite a bit tipsy. A good thing the car wasn't too far away. Chanel who seemed totally unaffected, guided me to the car. With my heels on, I wobbled all over the place. Giggling, I fell into the low car seat. I hadn't done up the buttons Chanel had undone so the front split open and displayed my legs, my stocking tops, garter straps and some of my panties. Chanel got behind the wheel. She gave me a hard kiss on the lips while rubbing her hand between my thighs and then drove home. I fell asleep in my seat.

Now, safely in her apartment, we sat down on her chesterfield. The nap home did me well and helped me recover from my drink. Chanel offered me a cup of tea as she turned on the TV to watch some Netflix movie. Chanel snuggled next to me with her head on my shoulder.

The movie was pretty boring but I didn't want to offend Chanel's choice. I guess Chanel thought it boring too since her head now rested on my lap. She slipped her hand under her head as a pillow. Her long painted finger nails grazed against the shaft of my growing erection which had slipped out the leg hole of my panties. Fully hard, Chanel no longer hid her intentions and wrapped her fingers around my member. She pulled open the front of my dress to fully expose me and take me into her hot, wet mouth. "Oh Joan. I just love your cock in my mouth!"

"Oh fuck, Chanel." I moaned back. "I love your mouth on my cock!"

Chanel shifted and knelt between my knees. She had me lift my bum so she could pull my panties down to my feet but didn't allow me to kick them off. There wasn't much stretch in them so when Chanel pushed my thighs apart, I was limited to the amount I could spread my legs. I had never been bound up as such but being restricted like this made me even hornier.

Chanel went back to work. She pulled back my foreskin to lap the head and tongued my pee hole. Any pre-cum that was now free flowing, she eagerly licked away. "Mmmm... This is better dessert that at that bistro!"

My body reacted to her efforts. I held her head as my hips jerked forward and my body spasmed but Chanel refused to be rushed. She grabbed my wrists then using only her teeth, Chanel opened her mouth wide and gently bit just below my crown making my whole body jerk in pleasure and pain. As she moved her head up and down, Chanel took in more and more of me until her lips surrounded my base. Her teeth scrapped my shaft as she lifted her head. I was panting to hard, I could barely catch my breath.

My orgasm was just on the edge. I tried to thrust my hips towards Chanel but sensing my impending climax, she pulled off. Still unable to use my hands, my hips continued to hump but fucked nothing but air. I cried. "Oh gawd! Please! Ooohhh... I need to cum!"

"Not just yet daring!" Chanel cooed.

She lifted my legs over her shoulders and pushed my knees to my breasts. She spread my legs but feet were still bound by my panties. My own legs stopped me from using my hands on my aching cock. Chanel took my aching balls into her mouth. Her talented tongue rolled them around. My pre-cum was pouring out and pooling on my tummy. She released her mouth-hold. Her tongue ran up my ass crack again and again and then pierced into my hole. As she tongue fucked me, my entire body was quivering with agony and ecstasy. I wanted... No, I needed to cum but was unable to. Chanel did not just have me at the edge, she had me hanging over the cliff!

Chanel rose from her knees. She had undone her dress and let it fall to the floor. Dressed only in her red lace and satin bra and panties, she was devouring me with her eyes. She pushed her panties down her beautifully shaped legs. Her hard cock pointed to me and dripped of her pre-cum. She pressed her tip against my hole and gently pushed until her knob popped through. My body reacted with a spasm. She slowly fucked my ass pushing herself all the way in and then pulling it all the way out. Each time she pulled out, I could feel my gaped hole pout for her to put it back in. My mouth was open and I panted like a crazed woman. I tried to tell her to make me cum but could only make babbling noises.

My whole body was shaking like crazy as Chanel continued to slowly and steadily ram me. Her staying power was amazing. While I had orgasmed a number of times, I had been unable to shoot my load. The pressure in my gut only continued to build like a volcano ready to explode. My mind was filled with paisley colours and shapes like I was on some sort of psychedelic drug.

"Gaaa...gaaa...gaa...aaa...aaah..." Expelled out from my gaping, drooling mouth. My arms, my legs, my body; all flopped around like a rag doll. Then suddenly my body stiffened as I experienced the biggest orgasm I've ever had. And then nothing.

grgy56
grgy56
1,564 Followers
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1 Comments
MatureandkinkyMatureandkinkyabout 1 year ago

Excellent Series!

Wonderful lighthearted arousing entertainment 👏👏👏

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READ MORE OF THIS SERIES

Snagged! Ch. 04 Previous Part
Snagged Series Info

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