Heart Breaker – Sexcapade #5

T. Watanabe was a 38 year old graphic designer from Brooklyn, only 5’7 but strikingly handsome and tragically hip. Like most hipsters he spent his Fridays reliving his days at NYU at St.Mark’s place. That’s where he met me. We hit it off instantly and I gave him my number.

When he called a week or so later to invite me to his loft I was ecstatic. Its not everyday that I met a man who isn’t afriad to date a girl who is three inches taller than him, who has a fetish for six inch heels. He was also just adorable.

I was 19 and the skinniest in my life, so my lingerie collection at that time was vast beyond comprehension. I picked out my favorite lucky comb or black lace accenting white satin and put on a slinky black dress. I was ready to turn heads and break some hearts.

It took me a little longer than anticipated to get to Brooklyn I was lost and unfamilliar, since I got there so late we decided to skip going out for dinner and a movie and just chill at his place. I was thrilled I felt so grown. This was the frist time I was at a man’s home without him being a memeber of my church or a family friend. I felt like a wild woman. I was determined to bed this man in the name of my own liberation.

Looking back he was nothing but a gen-X slacker that refused to grow up, his home looked more like a dorm than the living space of an acomplished adult, He didn’t even have a couch. He was hot so I didn’t care that his bed was pretty much just two matresses on the floor. It was comfy.

He cooked me pasta ( which was awful vegan crap) and played Wonderwall on his aucustic guitar, which is spanish fly for co-eds. After his serande I made my move, I shly put my lips to his and he gladly accepted.

He had very sexy full lips and they were heaven to taste.

“Can you sleep over?” he asked with a smirk.

“Oh yeah, I can, I don’t have school on friday.” I answered truthfully.

“School?”

“yeah, school”

“How old are you?” he asked pulling away from me.

“I’m going to be 19 next week. Why?”

He grimanced. “You’re only 18? I thought you were at least 20.”

“Does 2 years make that much of a diffrence?” I smiled coyly and kissed him on the cheek.

“My little sister is 21, I ussually have a rule to not date girls youger than my little sister.”

“Well that rule sucks penis.” ( this is actually what I siad. I was 18 what do you want from me?)

“I would be taking advantage of you, you’re just a girl, I can’t.”

I pouted and pulled my dress back down, I turned away from him feeling quite defeated, but being the quick thinking girl I was I thought of an out.

“Its 1 am , I don’t want to walk home all by myself, can I just stay here for tonight.”

He looked unconvinced.

“We can just watch movies.” I smiled innocently.

“Oh, okay.”

We ended up watching the original Zatoitchi : the Blind Swordman after discovering we both had a soft spot for meloramatic samuri flicks. Halfway through the movie I made my move.

“I’m sleepy.” I siad through a fake yawn.

“I guess you can sleep next to me.”

“Okay” I siad giggling on the inside. I peeled off my little black dress and nochilantly drapped it on his wierd looking artist chair. I sat next to him on the bed and gracefully took off my thigh highs. Then a lay next to him and closed my eyes. It was about 20 minutes before he turned the movie off and took off his pants. I don’t know if he thought i was really sleeping or not but I took the oppertunity to “accidentally” brush my hand agianst his crotch. He had a thick cock and it was hard and ready.

He gently took my hand and placed it by my side, I thought the game was lost. Then his hand
slowly rested on my thigh and he ever so lighlty traced the line of my thigh hips and waist. He followed swirling lace of my chemise. My breasts where almost spilling out of the demi cups of the chemise and he stealthfully tugged until he could see just a hint of areaola. He turned away from me with a groan.

I scooted my body toward him and put my arm around him.

“You arn’t asleep ,are you?”

“Nope”

“Go to sleep N’jaila” he said gruffly.

“Give me a good night kiss first,” I cooed as I playfully tousled his hair, he was silent.

“What is one more little kiss going to do? I coaxed.

“You’re a stubborn girl.”

“No, just still a brat.”, I took his soft hand and placed it on my softer thigh.

“One- and then I’m going to sleep.”

He turned around and we melted into each other. His hands were warm and softer that any other man’s I ever felt. They were heavenly on my body. It wasn’t long before I was stroking his fat cock through his boxers.

With all the blood it took to erect him , there wasn’t enough for his moral mind and his lustful one. Any sense of hesitation was gone.

He rolled on top of me and playfully buried his face in my breasts.

“I’ve never seen tits this big. I want to taste them,” he said. ” I want to taste you.”

Before I could react he was trying to force his face between my legs. I had never been on the receiving end of oral sex. The thought of man staring into my quivering virtue unnerved me. I had never seen it and I didn’t know if it was weird looking or not.

I thrust my hands down and intercepted his waiting smile.

“Wait, I’ve never done this before.”

His face was brighter than Christmas. I could his body shudder in sheer delight. I assume that he thought I mean I had never had sex before. Nothing could be further than the truth. I just never had oral sex. He seemed to be excited that I didn’t say anything.

“You’ll like it, let me, please?” He begged.

I relaxed my legs and he gently moved the cloth of my lingerie to the side. His breath was like fire and relaxed my body and let it engulf me. His wet , delicate tongue prodded politely around my privates, I wondered ,When is this going to get good? Sadly it didn’t. Perhaps this was his first time as well.

When he figured I was ready he slid his boxers down and knelt before men, his face like a child walking through the gates of Disney World. His breathing was heavy and he muttered excitedly to himself about how I was “only 18”, it seemed to titillate him now. He slowly rubbed his member on my opening. His breaths even more heavy and short.

He was bigger than my ex and when he tried to enter me, nothing happened. I was like trying to fit a Red oak tree in a doggy door. It just plain didn’t fit. I was worried he would be angry, that i had gotten him so excited and he couldn’t consummate his desires. My worries were unfounded and he seemed even more aroused than when he was licking me.

His face was red , his heavy breaths became labored breaths. T. was having a mild heart attack. I didn’t figure this out at frist, it wasn’t until he kinda started wheezing that I clued in. I ran to his living room and called 911, I didn’t know his address so I had to find his mail to tell the operator where to find us. They came is what seemed like forever. They took him and I was half way to the hospital before I realized I really had no way home from there.

I ended up staying the night in a chair next to T’s bed.

What T didn’t tell me is that he had a weak heart since his was a teen. He actually JUST had surgery on it a month prior to this. He as told no sex for at least three months.

This was our frist and last date.