tagTransgender & CrossdressersA Long List of Firsts

A Long List of Firsts


Authors Note: This is a work of fiction and is not a quick stroker kind of story. It's involved; with character build up and relationship development. One of the main characters is transgender and there are sexual interactions with that character. So if that's not your 'thing' you might want to check out one of my other stories. I do hope you give this one a try though. As always I appreciate all your comments and feedback.


Sitting on my deck, in a locally crafted driftwood chair, I can't help but admire the scenery before me. The air is crisp on this early September evening in Alaska as I watch the Kenai River flowing past on its way to the ocean. It seems like a lifetime ago that I was in a totally different place. I hear the distinct footfalls of high heels on the boardwalk leading to where I'm sitting and I can't suppress my growing smile. The young woman now standing beside me changed my life in a number of ways. Her waist length black hair flutters in the light breeze blowing across the water. I can see her nipples become erect beneath the red long sleeve t-shirt emblazoned with the logo of the new gentleman's club; her modest B cup breast standing proud make her look so seductive. The black mini skirt covered only to her mid thigh showing off her amazing legs. The sheer black nylon encasing them shimmered down their entire length. Seeing her bright pink toenails peaking out of her 4" pumps was the final straw for me. There was a sudden uncomfortable pain in my groin as my cock hardened at an odd angle in my jeans.

It's funny how simple things trigger memories in a person. Sights, sounds, smells and even feelings of pain or pleasure can spark a flashback. That pain I was now feeling as my cock strained against denim made me recall how all this began.

15 Months Earlier

It was Friday night, not long after leaving work, where I found myself in my favorite place. My home away from home, at least from the time just prior to my divorce until now, where I could relax before heading home or in this case to the mountains for the start of a long needed vacation. Athena's Gentleman's Club was the best place I could think of to kill time and allow the traffic to die down before making the drive to my cabin.

Being a regular at Athena's, I knew most of the girls there and they knew me; some more closely than others but I think the general conscientious was that I was considered 'safe' to hang around with. I didn't have the girls constantly hitting me up for dances anymore but rather using me as a safe haven to escape obnoxious patrons. When I did get dances, I always tipped well which also garnered me extra attention when not in the lap dance areas.

Tonight was no exception. Although it was still early, the place was busy. I was sipping my Morgan's and coke at one of the small tables near the bar (my usual spot) when I saw Jessie approaching. Raven, an ebony beauty with huge breasts, had just finished dancing and was mopping up the numerous one dollar bills before leaving the stage when Jessie sat down beside me. Jessie and I had become good friends over the past year or so of me visiting Athena's and she was also one of my favorite dancers. She was older than many of the girls there, in her late thirties, but she was still a knock out and very popular with the clientele. Her long chestnut hair framed her pretty face like an old school Hollywood actress. She was a bit fuller in the figure but more hourglass than over weight. Her neon pink bikini barely contained her generous breasts or hid her pouty nether lips. She adjusted the material at her groin before kicking off her heels and placing her stocking clad legs in my lap.

"You've been busy," I said, immediately working my thumbs into her aching soles.

"These two-for-one happy hour specials are killing me tonight," she groused then let out a contented moan as my fingers worked their magic, "That last guy wanted me to dance the whole time with my shoes on. It's not bad for a couple dances but he kept me there for eight!"

"Well that must've made you some good money. Did he tip well?"

"Nope, just paid for the dances and that's it," her head went back and she moaned again, "Damn you know how to make a girl feel good."

"Imagine what I could do if I could get my hands on the rest of your body..."

She brought her head back up and looked at me with a crooked smile, "I'd love to take you home with me but my boyfriend and your wife might not appreciate it too much."

"Ex-wife," I corrected.

"Sorry, ex-wife...fuck her. I forgot that it's now final but Mark would still kill us both."

"We don't want that now do we?" I confirmed as my hands moved to her firm calves.

"Mmmmm...I hate to say this but you'd better stop or we'll both get in trouble from management," she said, reluctantly pulling her legs back. Had it not been so crowded, no one would have giving a shit about what we were doing but Jessie was right given the current situation, we'd better not push our luck.

I finished my drink and had just set the empty glass on the table when Dawn appeared, scooping it up. She was one of the servers but I really wished she'd get up on stage. My cock became uncomfortably hard the minute she arrived. She's an incredible cutie in her early twenties and she was also my favorite server too. Not that the other servers weren't good or attractive but there was just something about Dawn that got me going. Her hair was long and black with just the slightest wave going on. It hung down her petite body to her tight little ass. Her breasts weren't huge like nearly every other girl here but they were perky and firm. It was obvious from her tight tank top that she didn't wear a bra to support them either. Her best asset, at least in my book, was her legs. They are magnificent, firm and not overly muscular but with nice shape. I think another reason I liked Dawn so much is that she wore sheer black pantyhose rather than fishnets like all the other servers. I like a woman in pantyhose or stockings...Okay it's more than just like, it's a fetish for me. But fishnets always seem to cheapen the appearance. Considering I'm in a strip club, fishnets are the norm and the fact that they give off a trashy, slutty vibe should be a positive for a place like this but they do little for me. So when I find a girl who wears regular stockings or hose, I truly enjoy and encourage it. I tip her better so she makes sure to check on me more often. One thing I noticed tonight though was Dawn wasn't her smiling, bubbly self. She was very subdued like she was distracted.

"Are you ready for another?" she asked almost mechanically, setting a bottle of water in front of Jessie.

"Thanks," Jessie opened the water immediately and took a large swig.

"Sure," I replied, "I'm gonna be here for a while longer."

Dawn left then Jessie stood and stepped into her heels, "I'm gonna go freshen up before I have to get back on stage." She kissed me on the cheek then whispered, "Thanks for the foot rub."

I smiled and watched her swaying ass as long as I could. I pulled out my phone to check the traffic and it was still a mess. Fortunately I wasn't in a hurry. It was the beginning of a well deserved two-week vacation so I was content to sit there and enjoy the endless parade of young, scantily clad women. I leaned back and watched a new girl on stage that was very pretty but didn't seem to be all that enthusiastic about being the center of attention. She was going through the motions but there was no passion or excitement in her moves. I hate to say it but she kind of killed the hard on I had going.

Dawn suddenly appeared by my side and knelt down once my drink was on the table. I was expecting her to say something since she went out of her way to be that close but when I placed the money for my drink along with a $2 tip on her tray; I noticed she wasn't even looking at me.

"What's the matter?" I asked.

"I don't want that up-tight asshole and his goons to see me," she replied, nodding toward three new arrivals to the club.

The one she referred to as 'up-tight' wore an extremely expensive suit that made him look very overdressed for a visit to a strip joint. His salt and pepper grey hair and deeply lined face made him look older than he actually was. His two companions, doing their best 'Men in Black' impressions, were obviously some kind of security for the older gentleman. Dawn appeared genuinely scared of these guys.

"Who is that guy?"

"My boyfriends step dad. He's a real prick."

"Why do you think he's looking for you?"

"Because he thinks I know what happened to Ricky," she ducked her head as the 'gentleman' scanned the busy room.

"You want me to call..."

"I need to get outta here without him seeing me," she turned a pleading gaze my direction.

"Do you have a car?"

"No, I take the bus to work."

I looked around then took Dawn's tray and set it on the table. She had a surprised look on her face, not knowing what I was up to. I glanced back at the three men and watched as the two body guards slowly moved in opposite directions looking for their prey while Mr. Up-tight held his position at the entrance.

"When I stand up, get up and walk in front of me toward the VIP room," I said in a very calm voice.

I stood and didn't give Dawn a chance to think about what I was asking her to do. She did as instructed and we walked casually toward the VIP room as if I was going to get a dance from this young lady. Sitting at the entrance was the bouncer who would check people in and out of that restricted area.

"Hey Manny," I called as I approached, "I gotta problem."

"What's happenin' Jack...did Dawn spill a drink in your lap?" he smiled.

Manny is a huge guy and to most, very intimidating but once you get to know him he's a genuinely nice guy. He and I had sat at the bar many nights in the past swapping lies until closing. Two things I knew for a fact; he considered all the girls here like his little sisters and God help the fool that ever fucked with any of them. At 6'-5" and probably 350 pounds of muscle, if you painted him green, you'd have a perfect stand-in for the Hulk. I'm 6'-1" and around 250 and I feel small next to Manny.

"You see those three guys that just came in," motioning toward the entrance, "Dawn thinks they're here to make trouble for her. You might want to check'em out."

Manny's smile changed to a fierce grimace and I could see his brow furrow as he stood. He gave an acknowledging grunt before he made his way to the front door. I took Dawn by the hand and maneuvered her toward the hallway leading to the dressing room for the dancers and the back door. Manny kept it propped open so he or the girls could slip out for a smoke. No one in their right mind would try and sneak in that way with Manny standing guard just a few feet inside. As I got to the door, I could see through the narrow opening the shadow of a man standing just outside. I turned to Dawn but she pulled free of my grip.

"Where are you going?" I whispered, stepping further from the door.

"Gotta get my stuff," she replied over her shoulder then disappeared into the dressing room.

I know what you're probably thinking, 'What's this guy doing getting involved with her drama?' I was asking myself the same question at that very moment, along with, 'Do I really need this hassle?' But when Dawn reappeared with a duffle bag over her shoulder, giving me those great big puppy dog eyes, what could I do? My inner Boy Scout or Chivalrous Knight kicked in and I had to help her. I had to come up with a plan to get passed that guy outside the door. Just then Jessie and Trixie (another beautiful, well endowed young ebony lady) entered the now crowded hall then it hit me.

"You girls want to make an easy twenty bucks each?" I asked in a low voice.

They looked at one another then back at me, both with cocked eyebrows. They must have thought I'd lost my mind or something to be propositioning them like that. We'd known each other long enough that for me to ask them such a provocative question, I was either drunk or high or just plain crazy.

"Really Jack?" Jessie sounded annoyed, "I told you I don't do that. The last guy who asked me..."

"I don't mean THAT!" I replied rolling my eyes, "I mean I need you two to distract the guy outside this door so he won't see Dawn and me leaving."

Again they exchanged glances. "Is it her Daddy?" Trixie asked with a bit of a southern drawl.

"No it's not her father but it is someone who may want to harm her!"

They looked at one another again then to Dawn before saying in unison, "I'm in."

"What do you want us to do," Jessie asked.

"I want you two to get that guy's attention and get him to turn his back to the door," I explained, "Then once he's distracted, ask him for a light. That'll let me know the coast is clear and I'll get her outta here." I pulled out my wallet and was about to remove two twenty dollar bills when Jessie stopped me.

"Put your money away, this is on me," she said then gave me a quick peck on the cheek.

She opened her clutch and produced two cigarettes, handing one to Trixie and moved to the exit. Trixie gave me a wink and followed Jessie to the door. They made a show of exiting while chatting loudly. I listened to them engage the guy outside then pulled Dawn with me to the exit. We had to move fast and quiet when Jessie gave the signal. I looked down at Dawn's towering pumps.

"Take those off," I whispered.

She gave me a shocked looked, "I'll ruin my hose."

"I'll buy you some new ones. Now take'em off!"

She complied with a frown.

"When we go out, go straight towards the black Jeep at the end of the aisle and go to the rear passenger side door. Wait for me to open my door then get in and lay down on the back seat, got it?"

She nodded.

"Hey baby, ya gotta light?" Jessie asked a bit louder than expected.

I opened the door and pulled Dawn with me outside and down along the building toward the parking lot. Once we turned the corner, I put her in front of me, aiming for my vehicle. We got in and I took my time passing the 'backdoor guard' and his new found friends before turning onto the street. He was so distracted by exposed breasts, he never saw me.

"So Dawn, where do you live?" I asked looking in the rear view mirror.

She looked at me for a moment then said, "Magnolia and Myers."

It took about twenty minutes to get there and as we drove down Myers toward her apartment complex, I noticed a black Escalade parked across the street. I kept driving.

"Hey you passed it," Dawn exclaimed.

"See that expensive SUV? It's my guess those guys in the front are more of your boyfriend's step daddies men." I turned right on the next street then found a place to park in front of some residential homes. "You need to level with me. What's going on?"

"What do ya mean?"

"What kind of trouble are you in? Why is your boyfriend's step dad looking for you and him? And more importantly, what have you gotten me into?" my voice was stern and I think it actually scared her.

She just stared at me for a moment then dropped her head and began to cry. I let her have a moment then pressed her again. Dawn looked up at me with her mascara running down her cheeks. She looked completely lost.

"Ricky stole some money from Earl," she sobbed.

"Is that his step dad?"

She nodded, bowing her head again.

"How much?"

She shrugged, "A lot."

"How much is 'a lot'?" I was becoming worried when she didn't answer immediately, "Hundreds...thousands...?"

She shook her head, "More."

"How much MORE?"

"I DON'T KNOW FOR SURE!" she shouted, then calmed down, "A few hundred thousand I think?"

This was getting serious. "I need you to tell me everything from the beginning and DON'T leave out any details."

It turns out that Dawn and Richard (Ricky) met at one of his step dad's businesses; a modest golf course near Los Angeles. He had other businesses but that's the one Earl spent most of his time at with the exception of his other golf course in Monterey which he made trips to several times a year for various charity events. Dawn worked for a temp agency during the day and was hired to help out with filing and some word processing projects. Ricky made advances and she fell for the guy. Right before her assignment ended Ricky had her do something for him. He had her connect a flash drive to Earl's computer in the evening before she left for the day then remove it the following morning; the last day of her assignment. She was reluctant but he made her feel so good and so happy she did as he asked against her better judgment.

A week passed and she didn't hear from Ricky then one day he stops by the club where Dawn worked nights to make ends meet. He said he needed her help with something and then they could be together regularly. She was happy to help if it meant she could be with Ricky. She went to his place that night and he laid out what he wanted her to do.

Earl was running an illegal gambling operation at his L.A. golf course and was using the Monterey course to launder the money at the charity events. The money would be driven there by a trusted person (Ricky) and stored until the event was over. Ricky was going to steal the next shipment and disappear.

"Wait a minute," I stopped her, "If he's the driver, he's going to be the first one they try to find!"

"Not if they think he was hit by a rival and killed," she countered, "Ricky, myself and two of his friends were going to make it look like he'd been robbed and fatally wounded in the process."

"What about a body? I'm sure he wasn't going to kill himself."

"He drew blood in small amounts for a few days. He pulled his car off the road south of Big Sur at a place they'd picked out, splashed the blood around the driver's side, his friend shot a few holes in the car and they pushed it off the cliff into the ocean. He left his phone on and by the side of the cliff so it would be found. We stayed at a little motel that night and then his friend Izzy brought me back here and said Ricky would be in touch. That was three days ago."

"And you signed up for this?"

"Jack, I...I love him. And he loves me. Things just got a bit outta hand."

"YA THINK!" my mind went into paranoid mode, "Did you or Ricky tell Earl or his guys where you live?"

"I didn't but Ricky may have sometime while we were dating, why?"

"Did he know you worked at the club?"

"Who? Ricky...of course he..."

"No Earl. Did he know you worked at Athena's?"

"I don't think so. Ricky didn't want anyone to know I worked there and I wouldn't have told him."

"Give me your cell phone."

She dug into her duffle bag and handed me a neon pink smart phone.

"Did he give you a number to contact him in case of emergency?"

"Ya," she took the phone back and scrolled through it, "Here it is."

I quickly wrote the number down then had her get in the front with me. I waited until we were driving then tossed her phone out the window.

"What the FUCK are you doing? Why'd you throw my phone out the window?"

"I'm not sure exactly what kind of technology these guys may have but I think they've been tracking your phone so I got rid of it."

She just looked at me, mouth a gape for a moment until it sank in. She must have felt scared and violated to be followed and tracked like that. It gave me a very uneasy feeling too because things weren't adding up in a good way for Dawn. I wasn't going to say anything just yet but it looked like Ricky was setting her up to take the fall for his handy work.

I decided to take her with me to my cabin since it was the only place I could think of that would be safe. I didn't want any visits from uninvited guests at my place here in town so it was the next best choice. I also didn't think they'd be able to connect me to Dawn just yet but I wasn't taking any chances.

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byDrakon66© 10 comments/ 33237 views/ 44 favorites

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