A Down Low Valentine's Day

"So.. Do you have any plans for Valentine's Day?"

"You know I don't, Jesse." I laughed.

I'd been living in LA for about eight years and aside from my girlfriend Valeria, I didn't have a very close group of friends--well, until I started my new job and met Jesse. We had quickly become best friends and he was one of the only people I knew I could trust and count on in the big city of Los Angeles, aside from Valeria.

That is, until our relationship came to an abrupt end back in December after eight long years. Valeria and I were going through financial hardships and she was dealing with a broken home and family drama; she was always a party girl and loved to drink but her drinking had become more excessive the harder things got between us and I suppose, she ultimately chose the alcohol over me.

So despite having a very toxic relationship with her mother she decided it was time for us to part ways and left me high and dry with a very expensive apartment and moved back into her childhood home. I was crushed; I was more depressed than I'd ever been and I hadn't even thought about going on a date or meeting anyone since she walked out the door.

Jesse was very aware of this.

"C'mon Jake, you've got to get back out there." He said.

"Yeah. Well, you know I'm not interested in getting back out there." I told him.

Valeria and I had always promised the other that we would get married one day; perhaps even have kids. I took that promise very seriously and I assumed she did as well. Now that she's gone, it's all I could think about. I was 100% ready to spend the rest of my life with her and that's all I wanted; I'd given up on the idea of dating and random hook ups. The sex with Valeria was worth more than any random could ever provide.

"And what about you?" I asked. "Are you going out with anyone?"

"Yeah, I'm seeing someone." He said.

"Oh really? News to me.. Anyone I know?" I asked.

"No, no.. This is our first date." He said.

"What's her name?" I asked. "Where does she live? Where are you taking her?"

"Jeez, what's with the 21 questions?" He asked. "I don't want to jinx anything.. so the less you know the better."

"C'mon!" I laughed. "You've been trying to push me out of my bed and into someone else's for two months and now you won't even tell me the name of some broad you're taking out for Valentine's Day?!"

"Just.. Give me a break." Jesse said embarrassed. "I'm really excited about this one and I want it to be perfect."

"Okay, okay. I won't pry." I told him.

Fast forward a week to the 14th..

I decided to hit the gym after a long and exhausting day at work after seeing all the women in the office showered with roses, chocolates, love and affection and all the men telling me about the "epic" night out they had planned with their significant others that somehow always seemed to end with them giving me the details of the wild and crazy sex they had planned in an expensive suite at whatever hotel they were staying at for the night.

I headed home, hit the shower, and hopped in bed. I cut the lights out and kicked back and started to turn on my favorite movie to keep my mind off the gaping hole that was missing from my heart otherwise known as Valeria.

But my quiet night in came to a halt when my phone started violently buzzing on my nightstand. The name that popped up on the caller ID was Jesse.

"Hey, man. What's up?" I asked.

"Umm.. Hello. Sorry to bother you sir, but I'm the manager of the Abbey here in West Hollywood and we've got a young woman here who is belligerently drunk and is a bit of a mess. She asked us to call you and see if you would come and pick her up."

"What?" I asked. "A young girl? This is my friend Jesse's phone. I don't understand."

"Yeah, that's her. She said her name is Jess and that she needed someone named Jake to come and get her. That's you, correct?"

"Yes, that's me." I said.

"So will you come and get her? If not I'm going to have to ask her to leave."

"Yeah, yeah. I'll be right there." I told him.

I hopped out of bed and threw on an old hoodie and some sweats and drove down to WeHo.

"Hi, I'm looking for my friend." I told the bartender. "I got a call from your manager about 20 minutes ago and he asked me to come pick--"

"Oh yeah, yeah." The bartender interrupted me. "You're here for that girl Jess right? She's out back sitting on the patio steps."

"She?" I thought to myself. "Why does everyone keep calling Jesse a girl?"

I walked through the bar and out the back door; sure enough there sat a girl with silky jet black hair that ran down her back and rested on her shoulders. Her head was hanging between her knees with her hands resting on her lap; she was essentially curled up in a ball on the stairs.

I slowly walked up behind her and put my hand on her shoulder.

"Excuse me, I'm looking for my friend Jesse." I said.

She jumped; startled by my presence and turned to look up at me.

"Oh, Jake." She exclaimed as she drunkenly threw herself into my arms. "Please, take me home. I need to get out of here."

I was speechless.

I grabbed her by the arms and removed her from holding onto my neck; I squinted and tried to focus on her face as hard as I could. It was dark and she had on make-up; she had black streaks of mascara streaming down her face.

"Jesse?" I asked. "Is that you?"

It couldn't be; everything about this person was completely female. From her face, the way she was dressed, her feminine curves, all the way down to her voice!

"Please. Take me home." He said.

"Okay." I said.

The manager wasn't lying when he said Jess was belligerently drunk; she could hardly stand much less walk. Jesse was a small guy; much smaller than me. He was only about 5'4 tall and weighed maybe 120 lbs or less.

"C'mon" I said. "I've got you."

I scooped her up into my arms and carried her through the bar and out to my car.

"Here, stand up for a minute." I told her.

"Thank you." She drunkenly mumbled.

I took a second to look her over once more now that we were out of the bar and under the street lights. She had big brown eyes and long black lashes; her skin was clear and quite natural for her made-up look. I could see the light brown freckles on her cheeks--the same as the ones Jesse has. Her lipstick looked to have worn off and her lips were a natural soft pink.

She had on a necklace with a small black and gold heart pendant; her silky black hair draped over her shoulders and I could see her collar bone. She had on a small almost bikini-like top with little spaghetti straps; her stomach was uncovered.

My car was the only thing holding her up as I unlocked the door and started to guide her into the passenger seat. I noticed she was wearing a short black skirt that was open in the back; it had several lace lines connecting each side of the skirt together but left the ass completely open and I could see the tiny black thong that she had on underneath. She had on a tight pair of fishnet stockings that were hugging her thick thighs. I could feel my cock starting to grow...

Her soft brown skin was completely smooth.

I brushed the hair from her face as I buckled her in.

"Jesse, what the hell is going on?" I asked as we drove to his apartment.

"Call me Jess." He said.

"Okay, Jess.. Why.. Do you look like that?" I asked.

"Huh?" She mumbled. "Look like what?"

"I don't know." I said, more confused than before I asked. "Why do you look like THAT?"

"Like what?"

"Hot!?!?" I exclaimed; I couldn't believe myself.

I looked over out of the corner of my eye and she had finally started to crack a bit of a smile.

"You think I look hot?" She asked.

"I don't know." I said. "I'm just trying to process this."

The drive to Jess' apartment was short but she drifted in and out of sleep on the way there.

"Where ARE we?" She asked before drifting back to sleep.

My eyes started to wander as she sat passed out in the passenger seat; her skirt was so short and the fishnets she was wearing were hugging her thighs so tightly that the thickness of them were bulging out of the top. I took one hand off the wheel and placed it on her thigh.

"We're almost home." I told her as I gently caressed her leg.

She placed her hand over top of my hand held onto it tightly; I could feel my cock begin to swell up again.

"You're the best, Jake." She mumbled.

When we arrived at her apartment I got out of the car and went around to help her into the house. She threw her arms around my neck once again and I scooped her up just as I had when I carried her out of the club. This time I could feel my hand instinctively grasp one of her ass cheeks firmly.

I lifted her out of the car and when I did her mouth dropped wide open and her face started to come closer to mine; I pulled back.

"Kiss me." She whispered in my ear as we walked up the steps.

"What?" I whispered. "No.. I can't."

"It's okay." She laughed as she raised up and softly nibbled on my ear.

I could feel the warmth of her breath on the wetness she left behind on my earlobe. I pulled away again but I knew my cock was rock hard in my sweats.

"Where are your keys?" I asked.

"In my purse." She said.

I sat her down on her feet and she leaned against the wall as I shuffled around her purse to find the keys. She fell over onto me and held herself up against my arm and shoulder; her hand placed against my chest.

She laughed as I fumbled with the lock.

"What's so funny?" I asked.

"You're hard." She said as her hand slowly ran down my chest and onto the bulge of my pants.

"Stop." I said, completely embarrassed. "C'mon lets get you into bed."

We stumbled down the long hallway to her dark bedroom; all the lights in the apartment were off and her bedroom door was open. The room was so dark it was like a gaping black hole.

"I've always had a crush on you" She confessed as she continued to try and kiss my neck. "I'm sorry I never told you."

"It's okay." I told her.

"No, really. I'm sorry I never told you." She said again.

"Never told me what?" I asked.

"I'm trans." She said. "I just haven't been able to fully come out and start my transition."

She had certainly sobered up a bit from when I found her at The Abbey.

"I hope you aren't mad at me." She added.

"Mad?" I asked. "How could I be mad? You're my best friend, Jess. This doesn't change anything."

"I want you." She whispered under her breath.

We were standing at the foot of her bed now; her arms wrapped tightly around me to keep from falling over. I stood towering over her looking down at her head which was resting on my chest.

"I want you." She whispered again. "I'm ready."

"You're drunk." I laughed as I placed my hand under her chin and raised her head to look up at me.

It was dark but the street light was pouring in through the shades of her window and I could see the glow of them in her big brown eyes.

"Do it." She said. "Please."

"Jess.." I nervously laughed. "I've never been with... A girl like you. I don't know if I could..."

She interrupted me before I could finish trying to safely navigate whatever I was about to say and grabbed a handful of my throbbing hard cock through my sweats; she squeezed it tight.

"It's just like any girl." She said. "Just put your cock in my pussy."

I could feel precum start to leak from the head of my cock as she squeezed it tightly. I couldn't bring myself to push her hand away this time; her touch felt so good.

"No.." I whispered. "I can't."

One of her tiny hands reached up and grabbed the back of my head and pulled me closer to her and before I knew it our lips were locked; my hands were shaking and my heart was pounding. I exhaled from my nose loudly as she shoved her tongue into my mouth; she latched onto my and refused to let go.

"Fuck." I exhaled as she continued to kiss and bite my neck.

I ripped my shirt off and over my head as she ran her hands all over my body and kissed my chest; she was literally worshipping me.

"I need it." She said.

"I don't think it's a good idea." I told her as she started to pull my pants down.

"Shh.." She whispered as she turned and fell face first onto the edge of the bed. "Put it in me."

My eyes had fully adjusted to the darkness of the room as I looked down at my best friend draped over the edge of the bed. Her skirt was riding so high over the hump of her ass that all I could see now was the tiny thong she was wearing. I stood there frozen; afraid to make one move. I thought about how good she looked and how hard my cock was.

Jess reached back and grabbed my hand and put it on her ass.

"Touch me." She said as she yanked my arm by the wrist and pulled me closer to her.

I placed both hands on her hips and started to run my hands along the curves of her body; over her ass and down her thighs and back up again. I squeezed her feminine hips as she pulled me in closer. My cock was rock hard and the only thing keeping us from touching were my boxer briefs and her thong. With both arms reaching back she held me in place as she pushed her ass back onto me and started grinding.

"Fuck me." She said. "Put it in me now."

I placed my hand in the middle of her upper back and shoved her down so that her face was buried in her mattress. I held her there as I used my other hand to slip off my briefs; down around my ankles they fell. I took a step back and used both hands to rip her tiny black thong off of her body; her ass completely exposed to me.

I put both hands on her cheeks and spread them as I kneeled down behind her to get a look at her hole; it was nice and smooth. I could see her balls which were very small hanging and her cock was in a small plastic cage. The line that ran from her small sack to her asshole made her ass look like it was an actual vagina. My hormones were raging and my mouth started to water.

"God damn." I exhaled. "Your ass is perfect."

Without thinking I buried my face in her ass deep and stuck my tongue in her hole. Her legs started to squirm as I went deeper and deeper and I could hear her whimper with ecstasy as I ate her "pussy." She started to move further up the bed in an attempt to run from my wild tongue so I placed my hand under her ass and shoved her up onto the bed.

Her legs were spread wide and her hole was completely open and ready for me to enter.

"Are you sure?" I asked.

"Yes." She whispered. "Fuck me."

Without hesitation I placed my the head of my cock at the opening of her hole and slowly started to shove it in; she tensed up as it stretched her pussy and slowly started to move back and forth. I looked down and let some spit dribble from my mouth onto my cock as I pushed deeper inside of her; I put one hand on her shoulder and pulled her back and my other hand was tightly gripping her hips guiding her backwards onto my cock.

She pushed back as I lunged forward and her pussy swallowed my cock down to the balls.

"Oh my God." I said.

We both froze and took a minute to enjoy the feeling of her tight hole wrapping itself around my cock; it pulsed and squeezed my thickness as it stretched to fit. I started to move my hips back and forth slowly; I could see her tight ass bounce as it connected with my thighs with every pump.

Jess sat up as I thrusted my cock inside of her so that her back was touching my chest; I wrapped one arm around her neck and throat and held her up as I continued to pump her ass. She turned and we kissed deeply.

"I'm going to cum." I said.

"Do it." She said. "Give it to me. Fill me up."

I thrusted harder.

I shoved her down with all my strength and held her head to the mattress as I pumped rope after rope of cum inside of her; pounding harder and harder with each ejaculation. By the time I was finished, I could hardly stand; my knees were weak and I collapsed onto the bed beside her. She flipped onto her side and I wrapped my arm around her; spooning her.

We fell asleep with my hard cock still inside of her; my cum oozing out around the shaft and down her ass. Neither of us moved a muscle for the rest of the night.