Becoming Jessica Pt. 02

Drake had a surprised look on his face when he spotted me and mouthed [give me a few minutes] in my direction while holding up his index finger. I nodded I understood and gave him a flirty smile.

After the song I thanked my dancing partner and trotted back to my seat. Emma was still chatting it up with Kirk and I could tell she trying to rekindle an old love.

As I got back to the bar there were several lemon drop shots in front of our seats.

Emma said "Come on Jess, let's do some shots Kirk bought for us."

After I did a shot with Emma a waitress came over and handed me a glass of champagne and a note.

The waitress said "This is compliments from the gentlemen near the window." as she pointed toward Drake's table.

I thanked the waitress and opened the note which read:

"Hey there pretty. Glad to see you again.

Come check out the view over here, Drake."

I looked over at Drake's table and his hussy was now with one of his buddies on the dance floor along with the remainder of the harem.. In fact he was now sitting alone with a bottle of champagne staring at the city skyline.

Emma saw the note and said "Hello Jessica. Get your butt over there." I gave a coy smile and quickly primped up my cleavage while smoothing my dress. Kirk gave an approving wolf whistle as I began to make my way toward Drake.

I felt like a princess. I think he caught my reflection in the window because he immediately turned around and watched me walk toward him. I paid extra attention to my sexy strut and hip sway I had been practicing.

Drake had a big smile and stood up to greet me by saying "Hey there." He gave me a slight hug and kiss on the cheek as helped me to my seat.

I loved the fact he was attentive and treating me like a lady. He was my definitely my type.

Drake started off the conversation with a rather blunt "So I think you have something rather important to tell me."

I was shocked he knew. I mean why would he still want to talk to me. Didn't he like real girls?

I then began to mutter "Umm I don't know what to say; Ummm."

Drake then said [laughing] "I mean you haven't told me your name."

I could barely cover my embarrassment. Here I thought this hot guy knew I was a man when all he wanted to know was my name.

I was still blushing when I enthusiastically said "I'm Jessica, it's nice to meet you Mr Drake."

"It's actually Mr. Garner. Drake Garner" he replied in a very sexy James Bond way. I was definitely being wooed by this guy.

I quickly glanced over to Emma and she was now partying at the bar with Kirk and helping him pour shots for patrons. She definitely knew how to be the life of the party.

Drake and I went on to have a very nice, intimate conversation over a bottle of Cristal. He was from San Francisco and went to Stanford. He was a pharmaceutical rep and loved to play golf and hockey. He was a perfect gentleman and very funny.

He then asked me what I did for a living. I started to panic but just thought of Emma's workplace. I quickly replied "I work for a law firm in downtown Chicago. I'm an assistant in PR and Marketing."

Drake seemed impressed by my job and complimented me several times on my outfit and smile.

We continued with small talk on our jobs and life in general for a while until another slower song started to play. Drake got up and said like a true gentleman "May I have this dance Jessica?"

I politely obliged and got up as Drake took my hand. His other hand found the small of my back. Feeling his strong hands pressed against my lower back almost made me buckle. I was floating in girly bliss.

On the dance floor Drake held me in a more intimate way with both of his arms wrapped around my waist. In turn I placed both of my arms around his neck and slowly danced under his lead. Even with 3 inch heels, Drake was at least 3 or 4 inches taller than me. It felt wonderful to look up and into his sexy blue eyes.

We were cheek to cheek when Drake whispered in my ear "Jessica, I think you are one of the most beautiful girls I have ever laid my eyes on. I am so glad I met you tonight."

I kissed him on the cheek and whispered back "Thank you, I'm also glad I met you."

We danced to one more song. Drake began to hold me more close to his chiseled body. As we switched hand positions a few times I loved the feeling of his strong arms and broad shoulders.

Drake in turn gently lowered his hands a few times to feel my butt cheeks and upper thigh.

I think he could detect I was wearing a garter belt because after he passed over a garter bump he blew a kiss in my ear and said "So sexy."

I also felt his dick begin to stiffen against my belly. I felt so alive and alluring. I wanted this man.

When we returned to our seats I heard my mobile phone buzzing. I received a text from Emma. It read:

"Hey girl, Kirk got out early.

Heading back to our place 2 concoct some new drinks.

And who knows what ;).

Looks like you're in good hands ;).

B safe. Later."

The waitress came around for last call. Drake ordered a double scotch and I ordered another vodka martini.

Before the drinks arrived Drake positioned his chair directly next to me and stared deeply into my eyes. He placed one of his hands on my thigh and the other gently on my cheek. He moved in slowly and placed his lips on mine and began to kiss me.

Another girly rush came over me. My first kiss with a man was beyond my expectations. Drake knew how to move in for a kiss and close the deal. It was such a sexy moment.

I let his tongue enter my mouth as we both began to share each other's passion and attraction to one another. Drake was such a good kisser and I loved how he touched me.

When the drinks arrived Drake said "Hey let's take these back to my suite."

I agreed and said "But I'm not used to things going this fast. So don't get any ideas."

Drake assured me he would be a perfect gentleman and was happy to just to get to know me better.

In reality I was just playing a little hard to get, as suggested in the Glamour article I read earlier. I hoped Drake had some "ideas."

I gave him a quick kiss him and said "Perfect, Let's go."

On the way down to his floor Drake and I stood alone in the elevator. He took this chance to hold me close again and kiss me even more passionately.

"You smell so lovely Jessica." Drake said as he delicately kissed the side of my neck.

"Thanks you." I replied in a soft, feminine manner.

I loved rubbing his muscular chest as we embraced each other.

As we embraced Drake began to explore my body through the soft fabric of my dress. I felt so vulnerable and sexy knowing how quickly my wrap dress could become undone.

Drake began to hitch up my dress and explore my stockinged legs. I was under his control. Fortunately I was saved by the elevator arriving at his floor.

Once the door opened a couple of teenagers were waiting in the floor lobby. They laughed and told us to get a room.

Drake replied "Don't worry, we're on our way."

I just giggled as Drake escorted me down the hallway.

Once in his room Drake placed our drinks on a table beside the sofa and took off his tuxedo jacket.

Drake's arms and shoulders rippled through his fitted dress shirt as he turned to use the bathroom. I loved checking out his nice ass as he strutted away. He was unbelievably sexy.

I settled down on the sofa, crossed my legs, and sipped my martini. I tried to look sexy in a 'come hither' kind of way as I waited for Drake to return.

I was definitely feeling the effects of the alcohol. I kept reminded myself to keep a level head and not let Drake get too far with me. I don't think he would like the fact he was with a man dressed as a woman. Had I been a real girl I probably would let Drake have his way with me.

Drake returned and was now just wearing an untucked t-shirt and his trousers. Again I admired his ripped arms and sexy chest under his tight shirt.

Drake turned on the Bose system to some sexy jazz music, grabbed his scotch, and sat next to me on my right.

As I glanced around the room I said "Gee this is a really nice suite Drake."

"Thanks, I've enjoyed it this week. Sucks I have to fly home tomorrow morning. 7 AM wake up call. Ugh." Drake replied.

I then inched closer to Drake and put my dainty right hand on his muscular left thigh.

Drake in turn extended his left arm draped it around my shoulders.

I began to feel so sexy and vulnerable. I moved in closer and placed my left hand on his hard chest and settled my head on his left shoulder. I felt a small shiver through my body as Drake drew me closer.

With my delicate cheeks nuzzled close to his slightly stubbled face I could smell his manly scent. Part woodsy from his cologne and part citrusy from his aftershave.

I began to massage his masculine chest as I looked up at him.

I stared into his steely blue eyes and said, "Hmmm I love the way you smell Drake. It's perfect."

Drake took his right hand and gently caressed my nylon covered crossed legs and drew me even closer. He lowered his sexy lips and kissed me softly as his right hand slowly began to explore further up my dress.

It was an electric feeling. Passionately kissing Drake while his strong hands caressed the tops of my stockings and a bit of my bare flesh.

I took my left hand and reached under Drake's t-shirt and continued to massage his chest. My hands passed over some subtle chest hairs between his hot pecs. I was loving this.

I softly whispered "Ohhh Drake." as he began to kiss my neck and upper regions of my cleavage.

"You are so sexy Jessica." Drake said in a passionate way between his kisses.

Drake's mouth returned and our kissing intensified. Our moist lips and tongues exploring each others mouths. It felt wonderful. It felt so right. I wanted this man, but I knew I couldn't go too far.

My left hand drifted down Drake's chest and came to rest near his belt buckle. I began to lightly rub the outline of his hardening cock. He felt huge through his pants.

Drake tried to explore my bare thighs above my stockings but with my legs still crossed he luckily couldn't get all the way up.

In a soft and sexy way I said "Ummm I never go all the way this soon Drake. But I can do something else for you."

"Yes" Drake said with a slight moan as we continued to embrace in foreplay on the leather sofa. .

As a signal Drake began to spread his legs a bit and slid off his dress shoes.

I took both of my hands and nearly ripped off his shirt. Drake helped me take it off as I propped up on my knees to get into a more comfortable position on the sofa.

I was out of control as I explored his muscular chest. I gently kissed his neck while my other hand started to unbuckle his pants. After undoing his buckle I partially unzipped his pants which allowed my hand to rub his hard dick which was still contained by a tight pair of boxer briefs.

With some help from Drake I lowered his pants and turned my entire attention to his cock. I teased him by rubbing both my hands up and down the outline of his hardon. I lowered my head gently kissed and licked the head through the fabric of his boxer briefs.

"Oh baby, Jessica. Yes." Drake moaned.

I slowly inched his briefs down to reveal Drake's thick, manly dick. It sprang up after I finished disrobing him. He was easily bigger than me. I guessed 7 or 8 inches with a nice, circumcised head. It had a nice amount of veiny traces along the shaft. It was perfect.

It felt huge in my girly hands as I stroked Drake's raging hardon up and down. His moaning increased as I paid particular attention to the soft and sensitive ring of flesh around the base of the head.

"Oh yes. Right there baby. Sooo Good." Drake whispered.

I had never sucked a guy's dick, but I had practiced on a dildo before in my fantasies. I also knew what I liked and what worked, so I felt pretty confident Drake was going to enjoy himself.

As I continued to work my hands on Drake's rock hard penis I went back up to kiss him in an indiscreet way of letting him know I was ready to take his cock in my mouth.

I softly said "Hmmm, Drake, you have a great cock. I love it"

Drake took the hint and said "Let's get more comfortable on the bed."

I replied with a smile and a nod as I stood up from the sofa. Drake did as well. We never left our embrace as Drake escorted me toward the bed. I loved the feeling of his strong hands wrapped around my waist.

As we reached the bed Drake turned me around and kissed me deeply. His hands began to explore fondle my ass through my dress.

I continued to massage his dick as Drake found the wrap tie of my dress and gave it a slight tug.

"So damn sexy" Drake passionately vented as he unwrapped my dress and saw my lingerie ensemble.

Holding me, he began to lightly kiss my neck and shoulders as he slipped the remainder of my dress off. He felt so good holding me. I loved his light kisses.

I responded "Ohhh. Hmm. Drake that's so nice. I love it."

Drake led me to his bed as we continued our romantic embrace of each others body. As he slid on the bed Drake looked at me and said "I want you so bad Jessica. You're so fucking sexy."

Drake was lying on his back, his erection growing as I slid down the bed over him. I explored and kissed his muscular pecs and abs as I made my way to his lovely cock. I continued onto his athletic legs and massaged them with my manicured hands as I began to gently kiss the length of his penis. I never felt so sexy and womanly. I was about to give my first blow job.

My hands began to stroke Drake's cock up and down as my tongue began to swirl around the tip and base of the head. I then kissed the tip and slowly began to take his manhood into my mouth.

I lowered my mouth up and down on Drake's cock and slowly took more into my mouth with each thrust. HIs cock tasted magnificent.

As I continued to suck Drake's dick I was careful not to scrape my teeth on the sensitive flesh around his the head. I knew how bad that felt and how it could ruin the moment.

In between taking Drake's cock in my mouth and licking the underside of his shaft, I took short breaks and stroked his entire cock with a twisting, two handed motion.

I added my mouth to the two handed stroking of Drake's cock. I wrapped my lips tightly around the head and worked up down the sensitive area.

I knew I was doing something right when I heard Drake begin to moan and utter "Oh baby. Jessica. Oh that feels so good. Right there. Oh my fucking, oh my."

His dick had now grown to it's full length. My two hands and mouth could barely take it all in.

As Drake began to moan more loudly, my mouth, lips, tongue, and two hands began to work in unison. Both of my hands worked his shaft up and down while my lips pursed around his head.

At times I would try and take the entire length into my mouth and stick my tongue out to message the bottom of his shaft.

Drake started to breath more heavily. I knew he was close to cumming.

"Jess. Oh baby. Feels so good. Oh yeah." Drake breathed out.

I wanted Drake to cum in my mouth. I wanted to pleasure him. I then remembered reading in Elle's "SEX SECRETS" section to moan and give "hmmm" sounds through your nose and mouth when sucking on a dick. The sounds cause vibrations which further stimulate a man's penis.

As I increased my sucking and stroking I glanced up at him and began to give several moans and "hmms."

I briefly took Drake's cock out of my mouth and said "Oh Drake, your cock tastes so yummy. Hmmm. It's so big."

I feverishly went back to the sucking, stroking, and "hmms" with Drake's hard dick.

This appeared to set Drake over the edge as his body began quiver. He placed one of his hands over the back of my head and passionately yelled "Oh baby. That's it. Ahhhh I'm going to cum."

I felt some precum oozing from the tip of Drake's cock as I wrapped my pursed lips around the head to finish him off. Soon enough Drake violently jerked his lower body and thrusted his dick further in my mouth as he orgasmed.

Drake screamed "Oh Jessica. Oh baby. Oh. So fucking good, Yeah, baby. Take it. Take it all." as I sucked and swallowed his cum.

Gobs more of Drake's semen filled my mouth as I continued to pleasure him. His moaning started to die off and was followed by several deep breaths and exhales.

I swallowed and licked up all of Drake's cum. Needless to say I have never tasted semen. I have to say it did taste salty and warm, but I loved swallowing it knowing I just gave him an awesome blow job. It felt so feminine and so right.

"Wow baby!" Drake uttered. "That was something else. That was great. I'm in love".

I kissed Drake on the cheek and whispered I needed to visit the bathroom to clean up a bit.

As I got off the bed I kicked off my heels and stripped off my garter belt and stockings and grabbed my purse. Now just wearing my bra and boy shorts, I remembered to keep walking and moving like a girl. I wiggled my butt as I scampered away from the bed and gave a quick glance back at Drake. When I saw he was fixated on my ass and sexy gait I gave a girly giggle and put my hands over my mouth to hide my slight excitement. I loved the fact he was checking out my backside. It was quite flattering.

In the bathroom I sat down and peed after untucking my genitals. After popping them back in for a 3rd time tonight [It was getting easier each time] I put my thong and boy shorts back on smoothing out my girly region.

I was pretty sure I was going to spend the night in his bed so I checked out my face to see how my makeup situation was looking. I decided to remove some of makeup and my jewelry for more of bedtime look. I noticed when I removed some of my blush and foundation my beard shadow was showing. I started to panic.

I remembered a tip from a makeup tutorial for crossdressers on YouTube which suggested you can use a men's electric razor during the middle of an outing to keep your shadow from reappearing.

Thankfully next to one of the sinks was Drake's electric razor. The music was still playing in the suite so I decided it would be safe to use his razor really quick.

The trick worked. My shadow was gone after using the razor and blending in a thin layer of foundation.

I took a sleep headband from my purse and put it around my hairline. I then removed some of my eye makeup and lipstick. Part of my girl emergency kit included a little toothbrush which I used to freshen up. I also put on a little lip gloss/plumper to keep my lips fuller and sprayed on a little perfume in order to stay as girly as possible.

Since I didn't have any PJ's I took it upon myself to put on Drake's white dress shirt he had on earlier. It was way too big for me but it felt so nice and sexy to wear.

When I came out of the bathroom I pranced back to the bed. I giggled a little when I noticed Drake was fast asleep. I knew he had an early fight so I could hardly blame him.

I pulled back the covers and bedspread and slinked up next to him. He awoke briefly as I slid the covers back over us.

"Goodnight pretty." Drake said in a bit of slumber as he gave me a nice, short kiss.

"Thank you, goodnight Drake." I whispered back and kissed him on the cheek. .

I slid and turned my body away from Drake on the silky satin sheets. As I cozied up to him he wrapped his arms around me in a spooning position. As I fell asleep the last thing I remember was him kissing and nudging my ear as I held his hands close to my body. I felt so comfortable with him in bed.

When I awoke I looked at the alarm clock and it said it was 9:35 AM. My head hurt from the champagne. I was still wearing Drake's shirt and noticed he was gone, as were his suitcase and things. He was probably on his flight back to San Francisco.