More Vegas Nights Pt. 03

Continuing from "More Vegas Nights pt.2" that will continue in the future under "Adventures with Jenna" so that I can share more of the many adventures with Jenna over our years of friendship that I'm sure you'll enjoy, remember my stories are true accounts of my life growing up in Las Vegas.

It had been two weeks since my amazing day with Jenna, the way everything happened that day the fun I had dressing up with her playing around, then the two of us sucking her client off was an extra treat but having sex with Jenna was amazing.

We personally, spiritually, and sexually connected that day, possibly we had our connection from our first meeting, Jenna catching me in my car, sitting in a dark parking lot dressed in women's lingerie watching women like her walking past me while I jacked myself off.

Jenna was cool, fun, sexy and so down to earth making every minute of time spent with her a pleasure.

It was finally our Saturday, two weeks since we were together, just hanging up the phone with her after finding out her location so we could meet up an get our party started.

Same motel as last time but a room more towards the back still on the first floor probably because of her high heels not being to stable going up and down stairs.

I couldn't wait for this day to come anticipating what might happen once we get together, plus just getting to see her, hopefully having sex with her again occupied my mind most of all the past two weeks.

Over the last two weeks I spent time searching out new clothes hitting all the best laundry rooms where I routinely found sexy lingerie, nylons and pantyhose along with other items of clothing I might wear, including a couple of things I took just for Jenna.

I knocked on her door this time along with my two large JCPenny bags I brought a small suitcase for the items I wanted to keep long term and a bouquet of flowers.

When she answered the door I handed her the flowers holding them out for her to take, she was standing wrapped in a towel like she was fresh out of the shower, the prettiest smile on her face she reaches out for the flowers with one hand while her other hand held onto the door, the towel dropping to the floor exposing her perfect body while stepping back to let me inside.

I set my two bags just inside the door then reaching down picking up the towel and grabbing my suitcase before going inside.

I noticed one thing different about Jenna, when I bent down to pick up her towel the little strip of hair above her pussy was gone, she was totally shaved smooth.

Jenna has no problem being naked with a body like hers probably why she gets paid so much from her clients but she still try's pointing out flaws on her that just don't exist.

This time her room was a lot bigger with a little kitchenette, a full bathroom just off a small living room area with tv/vcr and a separate bedroom considering the last place was a queen size bed in a room with a small table two chairs and a small bathroom.

Holding her flowers "I brought you something too...Me!!" she said posing herself with her perky eraser nipples sticking straight out from her small grape fruit size shaped titties.

I didn't know where to look... her beautiful face, sparkling eyes, her firm ferky tits with always pencil eraser hard nipples or her firm tight flat stomach with dangling bellybutton jewelry dancing above her newly shaved pussy mound or maybe her long beautiful legs with perfect pedicured feet.

Feeling my dick hardening in my denim shorts while I take in the view, she turns around stepping towards the kitchen sink, bends over with her legs locked straight, her little ass spreading open like a peach exposing her tiny asshole and tight outer pussy lips, looks back at me smiling then stands back up straight proceeding to the sink to set the flowers in water.

"We are going to have so much fun this weekend!" she says.

"Take a shower so we can start... I'll be in to shave you in a sec..." she tells me.

My pubic hair was just starting to grow back after itching like crazy from her shaving me last time but overall it was well worth it.

I was standing in the tub showering when Jenna came stepping into the shower with me, sitting down on the side of the tub while picking up the razor from the soap dish.

Running her hand down my chest across my stomach examining the hair growth where she had shaved me before, then wrapping her fingers around my semi hard dick causing it to rise up and stand straight for her. With her other hand she shaved me smooth moving everything around to be sure no spot was missed then kissed the tip of my dick while she held it in her hand.

A rush of pleasure ran through me, feeling her touch again, watching her lips kissing the head of my dick knowing what was about to take place, all the pleasures we were about to enjoy together building up in me.

Now out of the shower we took the bags of clothes I brought into the bedroom dumping them both out onto the bed, two piles of lingerie, stockings mixed together, bras, panties, stockings, garter belts, pantyhose, slips and assorted sleepwear all tangled together but clean, right out of the dryer. Since most of it was black in color the white and beige items stood out and the nylons a tangled mess.

"Guess we have work to do!" Jenna said while she slipped on a long purple night shirt throwing me a long black satin night gown to put on.

"I brought that for you... its one of mine!" she said as she hopped on the bed pulling at the clothes to separate them.

When we first met she offered for me to try on her heels while I dressed up in my stuff since I didn't have any heels of my own. I thought her offer was special and greatly appreciated it. To have such a sexy, stunning woman make such an off and to have that moment turn into this, unimaginable but forever thankful.

Having someone, any female sitting going thru these clothes with me would be special but having a woman like Jenna, a total eye catcher for any man sitting here sorting through my pile of stolen lingerie sizing them up for me to try on or not.

Well my dick was rock hard signs of a wet spot appearing on the gown around it.

"Before we start dressing up... I brought something for us!" she tells me getting up off of the bed going towards one of her suitcases sitting on the floor.

She returns to the bed holding a small satin satchel bag, sitting back next to me before dumping it out between us, the items hitting the bed with some weight.

On the bed between us were two identical silver metal butt plug's with a tube of special lubricant.

"I got these for us... one for you and one for me!" she says happily picking one up handing it over to me. The damn thing was heavy, cold chrome metal shaped like a really big egg with a short T shaped handle.

Rolling over on her side her little ass pointing my way with one hand pulling her ass cheeks apart "Put mine in!!!" she tells me with a smile, blowing me a kiss.

We are going to be feeling the exact same feeling holding these in our asses I began thinking right about the time she said that same thing to me.

Twisting off the cap for the lube she took the tube from me squeezing some onto her finger before handing the tube back to me. She took her lubed finger and began rubbing it around on her extremely tight puckered pink asshole before pushing the tip of it inside her moving it around a little before going to the second knuckle, a few times in and out then she moved her hand away for me to insert her buttplug.

My dick was rock hard, looking at her tiny tight puckered asshole looking wet from the lube she had just applied, watching it wink and pulse at me as I stared wanting badly to slide my dick inside it.

The shape and size of the buttplug seemed to be way to big for such a tiny hole but as I pushed it, stretching her little hole open it sucked right in with little pressure swallowing the tapered heavy metal plug to its resting point while her little tight hole gripped onto it tightly making a seal holding it in place. I was ready to cum just watching what had just happened.

"Your turn!" she says changing her position on the bed.

"Get into the same position I was in... do what I did!" she tells me while she picks up the tube of lubricant taking off the cap.

No sooner than I was on my side Jenna pushed my ass cheeks apart with one hand while she started rubbing her finger around the outside of my puckered hole causing me to moan. I love the feeling I get playing with my ass but feeling her finger sliding around poking at me sent waves of pleasure through my body.

I was close to cumming just from her finger and Jenna sensing that turned me a little putting her mouth on my cock, taking it in her mouth just in time to catch my load. She was moving the tip of her finger inside me only for a quick second before inserting it deep to the third knuckle causing a flood of cum to burst, exploding my hot load right down her throat.

Still wiggling her finger around inside me rubbing right on a certain spot I couldn't stop cumming, my dick thrusting throbbing in her mouth draining me of everything I had as her finger worked me.

Once I stopped orgasming, drained of cum, she turned me back over to my side and inserted the heavy metal cold plug into my ass. My dick didn't care it was drained, hanging limp, something that hasn't happened before with Jenna, it always stayed semi hard till now and I'd never cum

like that before.

She laid next to me our bodies rubbing together, the material of our clothes rubbing against me started to bring my dick back to life.

"Time to get dressed!" she says getting up off the bed standing pulling me up to my feet.

"We have things to do!" she said as she drags over one of her three suitcases pulling it closer to the bed before opening it.

Inside this suitcase she had a dozen pairs of heels, a few satin or cloth bags all tied closed along with a shoebox and a couple department store bags.

She pulls out a couple pairs of her high heels then flips the top closed pushing the suitcase towards the wall before reaching for her second suitcase pulling it to her and opening it up.

Inside this suitcase filled with clothes I was able to see corsets, bustiers, garters and other lingerie and sexy outfits all mixed together.

Every little move I made I could feel that buttplug inside me having to tightly squeeze my cheeks together not wanting it to fall out from the weight of it but he feeling was making me hard again.

Jenna then pulled this black piece of clothing out of her suitcase throwing it towards me, it was the same black girdle slip thing she had me wear last time we're together.

I watched her perky titties bouncing around under her purple sleep shirt while she picked out what I was to wear telling me that we can spend time later trying on all of the different clothes I brought but for now we needed to get ready for her client.

I knew we would be sucking another dick together sometime today but had no idea it would be happening so soon.

I watched Jenna teasing me while she helped me put on the tan pantyhose she wanted me in first before I put anything else on. The feeling of the nylon material squishing my dick against my body had me erect able to see it plainly through the shear material was a turn on for both of us.

As I dressed up in the clothes she wanted me to wear she continually fixed and adjusted me making sure to tickle my dick with her fingernails every chance she had.

Now the tight pantyhose helped support the plug in my butt allowing me more freedom to move.

Long legs look so sexy in stockings and we both had great legs only mine more thick and muscular than hers but both irresistible to men when wearing stiletto heels.

We had finally finished dressing up in our outfits looking like a pair of women in penthouse magazine, our sexy black lingerie looking at ourselves in the mirror hanging on the door.

This time her beautiful perky tits not exposed but covered in a web of black straps crisscrossing multiple times over her chest leaving only her eraser nipples pointing out in the open. A lacey black high waisted garter belt covering her midriff down just above her pussy with a dozen garters hanging down attached to her black fishnet stockings.

The heels she wore so tall and spiked with multiple straps and buckles holding them on to her feet giving her a dominatrix look with a floor length shear black and red robe tied at her waist.

With me already in pantyhose Jenna put me into a pair of black saitn panties that fit snug on my ass and tight on my dick and ball sack making me appear dickless under the material. Then helping me pull the tight black girdle on constricting my body into female form like she was dressing a manikin tugging and twisting making sure everything was straight and in the proper position.

Then Jenna went over to her suitcase pulling out a pink silky bag opening it removing a breast form that looked just like a natural boob with the raised nipple and everything handing it to me before pulling out the other of the pair.

Soft and squishy in my hand about the size of a grapefruit cut in half just like her tits.

"Better than rolled up pantyhose...even though the pantyhose worked well filling out a bra!" she says while helping me put them into position, the look and feel of them just upped my game.

After putting on black fishnet stockings attaching all the garters into place my long legs looking amazing in the mirror finally finishing my outfit with her open toe strapy 4" stilettos with two straps around each of my ankles, making Jenna still stand just a bit taller than me in her 6" stilettos.

We found that it was easier for me to walk in the 4"or 5"inch stiletto heels rather than her 6" inch stiletto heels even though I did alright if they were 6" platform heels like strippers wear dancing.

The whole time we were dressing we were talking about the plans she had for us letting me know that she had made plans for the man who came over the last time we were together to come over so we could service him again and that he was the one who paid for the room we were in and that she was staying for a few days.

She told me that he would be over soon and that he requested that I be here with her when they talked, part of her deal for that to happen was for him to pick up her room tab for the weekend along with her normal fee.

Then she proceeded to tell me that after we finished with him that he wanted us to take care of one of his business associates as a favor to him but not for free and that the man was going to pay her almost double her normal rate possibly more.

The two of us were going to service a couple guys in the middle of us playing around together dressing up and stuff.

"Ok" I told her checking myself out in the mirror eyeing her at the same time. My cock no longer attempting any escape from the confines of the sexy lingerie gripping my body, the feeling of the weighted butt plug inside me now feeling normal accustomed to the pressure.

Watching Jenna checking herself in the mirror rubbing her hands all over her sultry body in the back of my mind wondering what she does during the weeks when she's back at home, a teacher, a secretary, a nurse, a cop or lawyer who knows maybe just a clerk at a local store I was not asking and really didn't care but sure helped my fantasies.

Hearing a knock at the door I came back to reality, the older man from two weeks is here.

Taking me by the hand Jenna walks me with her to the door, as we get there she plants a kiss on my lips prior to opening the door.

"It's all you baby!" she says opening the door.

The man enters giving Jenna a hug then looking to see me standing there close bye. Jenna closes the door behind him while he's looking me over, holding out her hand for payment.

He reaches into his front pocket pulling out a big wad of cash handing it over to her, once she has the cash in hand she reaches up putting a hand on my shoulder pushing me downward.

"Suck his dick baby...get down, undo his pants... he wants a blowjob baby... Suck him off!" she tells me.

I follow her instructions kneeling down to get into position as she stops me telling me that good girls dont kneel they squat so they won't ruin their stockings.

Squatting down balancing myself on the heels I undo his belt, unclasp his slacks and pull down his zipper, his slacks dropping to the floor he was commando, his balls hanging lower than his limp dick, the tightly curled grey pubic hair surrounding it.

Jenna's hand now at the back of my head gently pushing me towards his dick, without touching it with my hands I opened my mouth taking the entire thing closing my lips around it at the base, my warm wet mouth engulfed him in one motion the tip of his soft dick just touching my throat feeling it grow bigger in my mouth.

Jenna had her hands rubbing around on his upper body while hugging him and kissing his cheek while I sucked his dick.

After a few minutes she suggested that we move to the couch so he could sit and relax while I sucked him off.

I suggested we move to the bed so he could lay down and we could lay next to him giving me better access which is what we did. On the bed Jenna was putting her tits to his face while I wrapped my hands gripping his balls and shaft tightly as I lowered my mouth onto him my warm gooey saliva filled mouth taking control of him, my tongue working around his growing cock head as it swelled up getting increasingly hard only this time his shaft was thickening as well swelling up to a more semi erect state, a familiar bitter taste his precum starting to mix with my saliva.

Sounds of a sloppy wet blowjob filled the air as I rigorously sucked and slurped on his dick showing my appreciation for his kindness and wanting me there with them.

Then out of no where his body stiffened up again while Jenna quickly reached for my head to hold me down, his entire dick stuffed in my mouth he unloaded blasting a heavy load of salty cum into my mouth down my throat my reflexes fighting off vomiting as I swallowed his load then one more twitch in his balls for a second blast of cum till Jenna let go of my head allowing me to breathe.

After taking a deep breath I took his cock back into my mouth licking it off with my tongue sucking the bulb of his dick as it went soft.

That was easy I thought to myself, Jenna getting paid for it was a win win to me.

While he was standing buckling up his pants he says

"Thanks for the blowjob honey!" he tells me

Then looking at Jenna he says "Make sure you two take special care of my friend later... Jenna darling... you do anything he wants... I mean anything!" he tells her then looks over at me "anything!"

Reaching into his back pocket pulling out his wallet he hands Jenna some more cash only this time he also hands me a hundred dollar bill before walking out the door.

Jenna looking at the money he just handed her hands me two hundred of it "You earned this baby!" she said with a big smile her lips sparkling from her lipgloss.

"Lets have a glass of wine" she says "We might need a buzz!"

"It will also wash the taste of his cum out of your mouth!" she added with a laugh.

While we sat drinking our wine we talked and she was asking me about sucking dick, when I started, how many guys, that kind of curiosity so I told her.

I told Jenna about Bill and Cindy, about my going to adult book stores and sucking dicks thru gloryholes.

She seemed fascinated by what I was telling her and at what age I had started. For the first time ever being around her my dick wasn't seeking attention almost forgetting it was there.

After we finished our second glass of wine Jenna stood up taking my hand leading me to the bedroom, She looked so amazing walking in front of me in her towering stiletto heels, her ass sharply snapping side to side like the pendulum of an old clock, hypnotic in motion.