Nick and Sandi Meet for Lunch

This happened a few years ago, but I fondly remember the day. I'd been cross-dressing for years and had yet to meet someone that was a dominant type. Mostly I met men that only wanted me to get a room, tell them the number and they would stop by and I'd blow them. I passed on that. I met TV/CD's. This was more fun, as we modeled for each other, but every one of them was a submissive, just like me! We would dress, comment on each other's clothes and tease each other. Sometime we would get really HOT and we'd end up stroking ourselves until we squirted. In all those years, only one gurl did we suck each other!

I had never really met a dominant type and Sandi was very horny this particular day. This was when Yahoo still had the user generated chat rooms and you could be anyone you wanted to be. I wanted to be Sandi. Mature, sexy, imaginative, and slutty. I wanted a man to chase me, I wanted to be the object of desire, I wanted to give men hard ons! Real women don't understand the power they have!

I had amassed a semi-decent wardrobe. Skirts, stockings, heels, a wig, panties, lipstick and even clip on ear rings! During these discussions, I made friends with a man named Nick. He was local, newly single, had his own place and absolutely loved special girls like me. He really was into the swinging scene, but he wasn't pushy. He called me "Sweetie".

This day though, Nick's real girlfriend had left town to visit relatives. He was off for lunch, had full balls and wanted to pound some sissy ass. Nick was very persuasive and eventually, I decided I needed hot cum for lunch! Nick was very straight forward (that's funny) about his need for a cock sucking sissy and depending on how I looked, my hot, tight gurlie ass may just get stuffed! I was so easy and he was such a gentleman and knew what to say to get me hot!

He gave me his phone number and I texted him. He immediately responded that he was in his apartment, he just worked out, he was naked and he was hard. He needed, no he required a mouth or ass to drain his balls. I asked for his address, screwed up my courage, got in my car and drove to his place. He lived in an apartment building overlooking the city. I had my bag of gurl things with me. I am a true closet sissy, I keep my clothes in my closet and when I travel I keep them in the trunk. I grabbed my bag and he buzzed me in.

When I got to his apartment, i could tell he was really Horny!! He instructed me to change in the front bathroom and left me to become Sandi. I changed as quickly as I could. Black thong and sports bra, white blouse, blonde wig, red lipstick, nude stockings, stretchy short black skirt and heels.

I walked out of the bathroom, only to be accosted by my friend. I was Thrilled! He kissed me with such passion, I thought I'd faint! I couldn't believe it. Is this how women feel all the time? I could feel his hard dick against my thigh. With his tongue down my throat, one hand up my blouse pinching my nipples and the other hand pulling my leg up, I was in heaven! I bent my knee and his hand reached my ass. Nick pulled my panties to the side and pushed a finger into my ass. I know I moaned! He knew what I needed and quickly pushed another finger into my ass. He was hungry, and I was the slut on the menu! We didn't have lots of time, but as we stood there, we broke our kiss and he said he wanted to fuck my ass. A blowjob was fine, but a girl with such a hot ass should be butt fucked. That girl was ME! I was so happy!

He pulled his fingers out and forced them into my mouth. "Get them wet, sweetie! They are going up that sissy ass again". He actually fucked those fingers in and out of my mouth. I had never felt sluttier! I was a true sissy. I now knew what my ass tasted like! Covered in my saliva, he dropped his hand, told me to reach down and spread my ass. I did exactly as he said. Next, I felt three fingers pushing into me. "take it, slut" I thought I'd faint.

As he was fingering my ass, I was rubbing his shaft and holding my cheeks apart. I had never felt more girlish nor so much like a whore!

"I don't have lots of time" he grunted, "get on the bed, ass up, face down and hold that ass open."

I ran to the bedroom and did as I was told! Fortunately, Nick had thought ahead, he had Kleenex and lube right on his night stand. I then felt a cold plop of something, obviously lube, on my asshole! He had aimed it correctly. Until now, I had only felt his dick. He told me he had an 8 inch thick dick and always came in gallons.

"I'm going to breed you Sandi, it is what you need" Nick was so matter of fact. I realized he was right. Here I was, dressed as a girl, I had shaved everything I could reach, and I was bent over in front of a naked man. "Ass up, face down"

"Nick, you're too big! That will never fit and I've never been fucked before!"

"Have you used a dildo, you slut?"

"Yes, I have. BUT never as big as you! Please don't split me and hurt me."

"no worries, I want you and your slutty sissy ass back here every day for lunch. You need to train your boipussy to take cock and your mouth to suck dick. Remember that."

Nick mounted me, he rubbed his dick up and down the crack of my ass. Teasing me, calling me names and pushing all my buttons. He then centered himself and I could feel the head spread my love hole.

"It's too big!! Don't, stop"

Nick held still and told me to push back when I was relaxed. In a few minutes, the pain had subsided some and I could feel heat deep within my ass. I twitched my ass at him and gently pushed back. I could not understand how I could love that stretching feeling. Here I was, pushing my ass onto the dick of a man I had just met! I felt so nasty and so alive!! My brain snapped. Just in that short time, Nick was able to bring out the real Sandi.

"Push baby, push back and take the dick, you were made to be a whore!" My body betrayed me and made my hole open to accept my fate as a sissy. I looked between my legs and saw the evidence, I was constantly leaking pre-cum. My tiny dickette twitched and I couldn't even see my balls!

Once I realized my ass could take the cock, I jammed my ass back at him and buried all 8 inches up my ass. I howled! I'm really vocal when having sex, this time was no different.

"FUCK ME! OMG! IT FEELS SO GOOD!!"

He grabbed my hips and started to fuck my ass. I was a sissy whore and I felt my malehood falling away. I wanted to be a gurl, tiny cockette, big tits, take hormones, be a whore. I loved it.

"you've opened up! What a cunt!" He started to pound my sissy ass calling me names - "Fucking Slut, Sissy Bitch and cum dumpster" My favorite was His Pussy Gurl!

It was lunch time, he had FULL balls, he was balls deep in me, i was a wet, willing cum receptacle. I could feel him harden even more, he was balls deep in me.

"Please, BREED YOUR SLUT!! Make me your bitch, get me PREGNANT!"

That did it, Nick unloaded his massive cum load. It was my first cumload, but certainly not my last!

"Take the cum, Bitch!! FUCKKKKKKK!!" and he exploded in my ass. I think I fainted.

When i came to, he had been quite the gentlemen and had cleaned me up, though i still leaked! He was 100% dressed. I went back to the bathroom, left panties on, they were gooey, took off Sandi and became the guy again.

This was how I wanted all lunch dates to be!