More Vegas Nights Pt. 02

Thanks for the responses to my stories which are all true recollections of my events growing up in Las Vegas aka Sin City.

Picking up from where we left off "More Vegas Nights" it had been two weeks since my encounter with the street walker by the Hard Rock Hotel and Casino who took a liking to me and my parking lot crossdressing, sitting in the car talking with me for quite some time talking teasing me getting me off for no money since I didn't have any but in trade for a short drive to the motel she was staying at so see didn't have to walk anymore in her 5" or 6" inch sexy stilettos.

I had been thinking about her every day remembering details from that night in my car saving every dime I made from doing small jobs around the neighborhood along with the money I made painting vacant units for a few of the smaller private apartment building owners including the owners of my building that owned two eight plex and two four plex buildings with a pool that I also took care of during the summer and when they went on vacation.

Having saved over fifty dollars the amount Jenna (Street walker) told me that I needed to have before contacting her on Saturday morning at 10am two weeks and one day from the day we met.

Two weeks have gone bye and during that time I collected more women's clothing to bring along with the clothing I already had like we planned in my car that night.

It was now time to call the pager number she gave me and leave my number for a return call so exactly at 10am I did just that. In just a few minutes my phone rang, answering it quickly it was her on the other end, just hearing her voice caused my dick to grow in my cutoff shorts.

She appreciated my punctuality happy to hear I had the money we agreed on then telling me the name of the motel she was staying at and room number telling me to bring all my stuff as soon as I can so we could start dressing me up for some fun. Just hearing her voice again made my dick hard.

I was on my way in seconds already having two large JC Penny paper bags with handles full of stuff to dress up in and play.

In minutes I was there knocking on the first floor motel room door, my car parked close bye with my bags in hand excited to have this opportunity, to have a hot looking hooker dress me up.

Jenna opened the door looking more normal than she did when we first met wearing a little tshirt, braless with her perky nipples pointy out like pencil erasers and a pair of baggy satin sleep pants the smile on her face calming my nerves inviting me inside.

"You came prepared" she says looking at the bags I was holding with me suddenly being a bit quiet and shy as I walked inside.

"I was happy to receive your page right at ten.... I wasn't sure you would follow through.... but I'm so happy you did." she said.

"I've been thinking about you" she said causing me to feel more relaxed not as nervous, my dick straining to be released from it confined environment.

"We are going to have so much fun today!" she tells me sitting down on the edge of the bed.

"Lets see what you've brought with you." grabbing one of the bags dumping it out on the bed. My assortment of lingerie poured out onto the bed with a rolled up paper bag topping the pile that was actually hidden underneath all of the clothes in the bag.

"What do we have here?" she says grabbing the rolled up bag before I could grab it.

"It's heavy" she says looking inside the bag.

"Oh....wow.... I didn't expect this.... how fun!" she said looking inside the bag with a mischievous smile across her face.

I had planned on working up to showing her my toys if it became possible but suddenly it was front and center.

"Money first" she says holding out her hand, reaching into my pocket I give her the fifty dollars as planned still holding another twenty in another pocket just in case.

Inside the bag were a couple toys from my collection of sex toys with a few condoms and tub of Vaseline just in case we get to play with my ass, not really knowing what we would be doing after dressing up if anything.

"I think you should take a shower before we start" she says getting up from the bed taking me by the hand leading me to the bathroom.

Barefoot she stood as tall as me her perky tits bouncing around with every step she took rubbing her nipples against the shiny material of her top like a giddy college girl even though she was older, my guess at her age thirties maybe late twenties but she could even be in her forties.

"Go ahead and shower while I get things ready..... I did bring heels for you to wear" she tells me.

Taking my clothes off my dick already standing straight out with excitement catching her attention.

"Look at you....excited to see me?" she says with a big smile staring at my boner.

"We should shave that hair " she says while looking at my patch of pubic hair as I stand somewhat frozen still my young hard dick standing straight out.

Reaching past me picking up a pink razor from the shower soap dish brushing her nipples against my skin at the same time turning on the water before sitting on the toilet seat cover.

"Come closer" she says reaching out her hand to take hold of my cock.

Feeling her soft hand gently grip my shaft pulling me closer towards her a bead of precum appears at the tip of my dick pulled out by her tug and fighting within myself not to cum right hen.

Holding my shaft in one hand and razor in the other she looks at the wet shiny bead on the tip of my dick, not wasting time she licks it off using the tip of her tongue then begins shaving me, removing the patch of hair with the razor occasionally kissing the tip of my dick while she shaved me.

In no time the hair was gone and she was washing the area off with soap and warm water, my dick fully erect as she washed me inspecting her work then telling me to shower as she let go.

After my shower my cock still hard as a rock as I dried off watching her set a piece of luggage on top a table in the room.

Seeing my current condition and we haven't even started dressing up in clothes and I was on the edge, she decided we needed to relieve my early excitement if we're going to enjoy the day.

While I was in the shower she had gone through the clothes I'd brought setting a few items to the side for me and others back into he bag.

Looking at the open suitcase on the table seeing multiple pairs of stiletto heels I unconsciously took hold of my dick tugging on it as I admired her shoes.

"Stop..... thats mine today!!! she yelled at me replacing my hand with hers, feeling her soft hand holding onto my dick had my head spinning, watching as she knelt down in front of me taking my cock into her mouth, her glossy lips wrap around the mushroom head of my dick, my first load cumming not long after that. She kept her lips sealed around my dick as I came shooting my jets of cum into her mouth while she swallowed keeping her lips around my shaft as I unloaded.

Looking up at me smiling she freed my dick from her lips to swallow again "I hope you can do that a few more times today honey!" she says licking her lips commenting on my taste and the amount of cum.

"You taste so good" she tells me "So sweet..... like me."

Standing pulling off her pajama bottoms exposing her naked lower half to me she walks over to the bed sitting on the edge opening her long legs her smooth pussy exposed topped by a tiny landing strip of hair.

"Here honey.... have a taste!" she says spreading her pussy lips open with two fingers as she laid back on the bed giving me a perfect view.

Dropping to my knees between her legs the sweet scent of her pussy spread open allowing me to see past her shiny light pink lips at the tight round pulsing opening of her love tunnel, her clit exposing from its folds visually drawing me in.

I gently touched the tip of my tongue to the nub rising from its hood covered in a clear gooey substance. She was soaking wet.

She held her lips spread open giving me words of encouragement and guidance telling me to lick her pussy starting at the bottom up to her clit, then to slide my tongue inside her as deeply as I could to get a good taste.

Feeling her wet pussy lips surround my open mouth I pushed my tongue deep inside pushing it as far as I could tasting her sweetness making my cock rock hard again rubbing against the edge of the bed.

She let me lick and suck on her pussy for quite some time enjoying her sweet sticky nectar, my face covered in her juices then suggesting we should start dressing up in our outfits. My face covered in her sweet pussy juice she smiled at me telling me I would be enjoying more of her throughout the day for me not to worry as I licked at my mustache.

I was obsessed with the flavor of her, tasting better than anything I'd ever had I was now possessed.

This day was going to be more than I could have imagined. I thought to myself.

We talked while going through the clothes that I brought asking questions about how I find them in laundry rooms and how sexy they will look on me even asking to keep a few of the items for herself.

Talking with her became so easy, looking at her in different stages of dress able to examine every inch of her tall fit body, touching her, feeling all her woman parts like a student receiving detailed information from a teacher.

We dressed up in many different sexy outfits seeing how they looked on us while wearing different pairs of her heels and learning to walk and balance myself in her stiletto heels.

After spending some time playing dressup in all the miscellaneous clothes she suggested we both get dressed in the black lingerie that she had set aside because she had an outfit similar to wear for our session.

It was now around two in the afternoon time flying by without concern we were having so much fun together, now both of us dressed in black with her in a black corset thing holding her perfectly shaped tits like two hands holding melons her perky eraser nipples pointing straight out. A sexy wide band garter belt clasped around her small waist with her sparkling bellybutton jewelry in plain sight, the black designer stockings showcased her long legs attached to the many garter straps, her feet covered by stockings just waiting for heels.

She had me in a pair of tan pantyhose to hide the light blonde hair on my legs because I didn't want to shave them so we put the pantyhose on first to hide my legs like I have been doing for some time.

Then she had me wearing this black girdle slip that was like a bra, a slip, and a garter belt in one, open at the bottom just long enough to almost cover my butt with eight garters hanging down four for each leg to support the black fishnet thigh high stockings I was wearing. She said this would give us better access to my dick and ass.

We rolled up a few pairs of pantyhose to fill out each of my breast cups making me look like having nice sized "C" cup tits.

The tight constriction of the girdle squeezed my entire body my cock constrained by the pantyhose stimulated by the rubbing of the girdle material against the nylon pantyhose rubbing my newly shaved area as we went through the heels she brought.

Just watching Jenna show me her different heels was turning me on.

"I know what I need to bring next time." she says to me making me realize that this wasn't going to be a one time thing causing my excitement to increase.

She didn't want me to wear panties so we would have an easier time later she explained while helping me into a knee length black slip with a slit running half way up trying to balance myself in her stilettos.

My hard cock pushing trying to escape from its confines against the silky pantyhose holding it pressed tightly to my body a spot of wet precum starting to appear.

Seeing that wet spot Jenna decided to put a pair of black panties on me sliding them into position under the slip binding my hard cock even more.

She kept hugging me, kissing my cheeks as she dressed me in the clothes making me look similar to her, both of us decked out in black lingerie and now both of us in tall stiletto heels that strapped to our ankles.

I fought back cumming as she squeezed and rubbed my dick through my outfit making my knees want to buckle from her touch. I was in dreamland.

Softly taking my head in her hand she gently pulled me towards her perky tits, putting a nipple to my lips I began to suck on her beautiful perky tit the nipple in my mouth like a hard #2 pencil eraser as I danced my tongue around it.

This was the best day of my life I thought to myself.

My first time ever dressing up with a woman in women's under clothing and she was beautiful, extremely sexy, so comforting, talking with me about the clothes helping me put the things on explaining everything to me when her pager went off snapping us both from our moment of closeness.

"Sorry....I must get that!" she says letting go of me.

Checking to see the number she tells me she must make the call asking me to stay quiet while she picks up the phone and starts dialing.

She starts a conversation with who was on the other end then saying that she couldn't right now, thinking she must not be wanting our fun to end "Hang On!" she says to the person on the other end covering the mouthpiece.

"I don't want this to end yet between us but I need to take care of this... he's a regular.... um.... would you like to... or maybe help me take care of this guy?" she asked me with a sexy grin.

"Hold on just another minute." she tells the person on the phone then covering the mouthpiece again.

"I just need to suck him off.... you can help.... or just watch us.... he'll get off quick and he pays me good.... come on.... it will be fun!!!" she says with excitement in her voice.

"Ok...Ok sure!" I replied as she uncovered the phone telling the person on the other end that she had a friend with her and if he was cool with that to come over and soon hung up the phone.

She grabbed onto me giving me the hottest kiss something we had never done mouth to mouth. The taste of her lips were amazing the sensation of her soft tongue inside my mouth causing me to suck on it like a dick tickling it with the tip of my tongue as she grabbed me between my legs squeezing hard bringing me back to earth. Whats happening right now I thought to myself.

With her there I wasn't nervous, after all I had spent a few years with Bill and I'm experienced enough to service this guy on my own but Jenna didn't know that.....yet!

She straightened things up around the room having me help put my things away to be continued later she promised as soon as we took care of this guy.

Once we had thing's cleaned up we laid on the bed with our hands exploring each other my finger finding it's way between her legs feeling the heat and wetness I had been unaware of till then.

She was actually getting excited her smooth soft warm pussy getting wet and her clit twice as big as when I first licked on it earlier and wanted to do again.

I could feel my cock covered in cold wet pantyhose surely my cum flowing freely at will from everything happening soaking the pantyhose that I was wearing.

Hearing a knock at the door caused a rush of excitement and nervousness mixed with a little fear, watching as she stood up opening the door looking like a lingerie model in a movie scene holding the door while this older well dressed man enters looking her up and down then looking over at me as she closed the door.

She instantly got his attention running her hand on his crotch pulling his focus from me back onto her as she stepped between us, blocking his view, pulling his eyes to her perky naked breast, gently pulling his head to the center of them for a moment before letting go holding her hand out for payment.

He was hooked, I could tell because she puts me into that same trance, just something about her.

She was quite the business woman getting her payment first I thought to myself... smart!

She put the wad of money in her suitcase then turned to him telling him to sit on the bed as she reached for my hand helping me up to my feet in her stilettos both of us towering in height wearing our sexy black lingerie outfits as he looked us both over.

No mistaking that I'm a guy wearing women's clothes with my mustache framing my upper lip down towards my chin but visually looking similar to a woman with long hair wearing clothing like we're from a lingerie catalog or xxx magazine.

She knelt down in front of him pulling me with her like two women to this one man we both knelt down between his knees as she ran her hand up his leg to his crotch looking at me to follow her lead.

I slid my hand up his other leg to meet hers as the man laid his body back on the bed we undid his belt, unfastened his pants, sliding down his zipper, opening them up for access to his dick.

Jenna tugged at his slacks pulling them down exposing his gray pubic hair topped dick hanging limp on his ball sack. I reached up softly taking hold of the dick lifting it with my hand. Jenna smiling at me blowing me a kiss I took hold of it, wrapping my fingers around the soft flaccid cock, she got into position taking the head of his dick into her mouth causing him to moan rather loudly.

"Oh....I've missed you." he says.

I watched as her glossy lips took hold of the cocks little mushroom head taking it down to my hand as I watched she placed one of her hands on top of my hand guiding me to stroke him while she suckled on him, our hands and her lips never separated while we stroked and she sucked.

It was obvious he was enjoying it from the sounds he made and the size of his old cock growing in response feeling more solid in my hand.

After some time she removed her mouth from his dick exposing a totally different looking cock from when we started, his cock head swollen almost purple in color about the size of a golf ball, the shaft thicker but real hard.

Looking at me giving me a look like it was my turn to suck I got higher up on my knees as she pulled my hand from gripping his shaft so that she was the only one with her fingers wrapped around his cock.

Looking at the head of his dick, I took it into my wet mouth sucking it, twisting my head around on it while Jenna watched holding it in position as I bobbed my head, sucking his dick now with her other hand controlling my head's movement and speed giving me verbal instructions to satisfy her client.

He was moaning more rapidly and moving his body around.

When she removed her hand from gripping his cock she pushed me harder downward to take his shaft into my mouth so I responded sucking down that entire shaft causing the man to let out another deep moan of pleasure.

His cock was not stiff and hard like others I'd sucked, barely semi hard but the head of his cock was super hard and smooth leaking a bitter tasting precum. She let go of my head no longer guiding my movements.

I sucked and serviced the mans dick while she was watching, rubbing my back and his chest succeeding on making us more comfortable together, more focused on him getting off of course and it was easy to see he was enjoying this.

She seemed to enjoy having me service her clients dick watching noticing the movements he was making moving on the bed knowing I was satisfying him making her client happy.

I felt her hand rubbing on my butt as she leaned in close whispering in my ear asking if I wanted to finish him off.

I was having fun being dressed up like a woman, like a hooker, with Jenna next to me I was sucking on one of her clients dicks, with the head of his cock in my mouth tickling it with my tongue.

Keeping his dick in my mouth I looked towards Jenna moving my mouth up and down on his dick seeing her smile at me gave me purpose for dressing like a woman.

Jenna then moved up on the bed placing her beautiful titties in his face, one of her hard nipples into his mouth while she stroked her hand against the side of his head.