I'd moved my print shop to a new location across town recently for a cheaper and more long-term lease. One of my first customers at the new place was a guy named Gerry. As we spoke, I found out that he was the owner of a small business as well. Gerry was a cabinetmaker and created some primo custom-built cabinetry. He'd come in to get some updated cards and stationery and wanted something with a little more pizazz than his former printer offered.

We spoke for some time, and I threw out a few suggestions, including using pictures of his work as the background. During our back and forth, I found out that we were the same age and both single once again. Our conversation continued far longer than my usual client interaction because we seemed to have a lot in common. Another hour later, we knew each other's life story, and I could see us becoming good friends.

When he realized how long he'd been there, he apologetically took his leave. I told him not to worry and that I'd had a good time getting to know him. After I watched him walk out the door, a feeling of infatuation washed over me. I couldn't explain it other than we seemed so similar, and it was so easy to talk to him.

The following day, I put together the proofs and emailed them to Gerry. He enthusiastically approved them with a phone call. While talking, he asked, "So, Jim, how long will it take to get everything done?"

"Well, the business cards will take the longest because they are four-color process. However, I can have the letterhead and envelopes to you in a day or two."

"Don't worry about that. Just let me know when it's all done, and I'll swing by and pick it all up at once."

"Okay, then I'll see you in a few days. Have a good week!" I offered a bit too excitedly.

After getting off the phone, I felt like an idiot for getting so excited about seeing him again. But, rather than feel foolish for my giddy behavior on the phone, I put that energy into doing my best work for him.

It was only two days later that I had everything finished for Gerry. I decided to drop it off to him since I had to run a few other errands anyway. I pulled up to his address and found that he had a substantial building alongside his home. I parked the car and headed inside the building's entrance. The first room was a small office area. On the desk, there was a sign that read, 'Please Press Button to Ring Bell.' In parentheses below, it stated, 'Do Not Enter Workshop Alone!' 

As I read the sign, I heard some sort of heavy equipment running back in the shop. I pressed the button a couple of times and noticed no interruption in the machinery noise. Approaching the door to the workshop, I found that it was unlocked. Pushing it open a little, I glanced toward the sound and saw a woman hunched over one of the machines.  

The fact that it was a woman didn't throw me so much as that she was wearing a short blue-jean skirt with nude-colored stockings and heels. She had terrific legs that had just the right amount of muscle tone. I always disliked the skinny legs on girls depicted in all the clothing ads. Gerry was a lucky guy to have a woman like that working with him.

I didn't want to yell and startle her, so I pulled the door closed and tried the bell once again. After waiting another minute or two, I placed the items on the desk and wrote a short note.  Sorry I missed you, Gerry. I was in the neighborhood and decided to drop everything off. Call me with any questions or concerns. Thanks, Jim.

Driving back to my shop, I felt a little disappointed that I didn't get to spend any time talking to Gerry. But as I pulled into my parking space, my mind wandered back to the sexy legs of his assistant. I imagined him moving in behind her as raising that skirt to find a bare leaking snatch just ready for the taking.

Walking back into my shop, my mind continued to stray as I imagined it was me moving in behind his assistant and taking her vigorously. Shutting off the equipment while slipping my hand up her inner thigh until I reached her stocking tops. Lightly grazing that soft, smooth skin just below her entrance. Pushing her torso down and watching the skirt rising to expose her plump derriere, left exposed by her black lace thong.

In my mind, my hands gripped and fondled her smooth, inviting ass. I could hear her breathing becoming erratic as I continued to caress those meaty globes. As my hand pushed the thong aside and tickled her pucker, the phone rang, breaking my trance. Looking down, I realized that both of my hands were in my crotch with my pants open. Even my underwear was pushed aside as I cradled my sack in one hand while stroking myself with the other.

I grabbed the phone on the fourth ring as I struggled to cover myself. "Hello," I offered as I picked up the receiver.

"Hey, Jim. This is Gerry. Did I catch you at a bad time?"

Realizing that I must sound as irritated as I was, I calmed down and answered, "No, just a little frazzled. Does everything look good?"

"You know that you didn't need to drop my things off, but yes, it looks better than good! Did you ring the bell or just leave the boxes on my desk?"

"Both, actually. I tried the bell a couple of times but got no answer."

"Again, sorry I wasn't here to pay you and go over things in person. How about I swing by your shop around six, and we can go have a beer. That way, I can pay you and thank you in person for your great work."

"Sure, that sounds good. I do have a confession to make, though. After trying the bell a couple of times, I broke the rules and tried the workshop door."

"It was locked, right?"

"Actually, no, it wasn't. But, I have to say that your assistant has spectacular legs! I hope that's not too inappropriate to say."

"Not at all. I'm sure she'd be flattered by your comment. She's not at all prissy and wouldn't be offended."

"If it's not too bold of me to ask, are you hitting that?"

"Well, let's just say it's complicated."

"Okay, I get the message."

"We can talk a little more about that tonight, but I gotta get back to work, or I'll never get done."

"Okay, see you later."

After hanging up, I followed Gerry's advice and got back to work too. I'd rather that than sitting around thinking about those fantastic stocking-clad legs of his assistant. Even with keeping myself busy, my mind kept picturing what I should have done to her.

I got to a good stopping point in my work and glanced at the clock to see that it was five-thirty. Having several invoices to print, I headed for my desk to get started. The time raced by as I clambered away on the keyboard. Startled out of my focus, I turned to see Gerry walking into my shop.

"Hey Jim, are you close to being done for the night?"

"Yes! An hour at the desk is far too long for me."

"I understand what you're saying. I hate paperwork more than anything, but we don't get paid without it, do we?"

"No, we don't. Speaking of which, here is your bill."

Gerry sat and wrote me a check while I closed out the computer and then walked around the shop to make sure everything was put away. With everything stored and his check written, I stuck it in the safe, and we headed out the door.

"So, where are we going?" I inquired.

"It's a little family-owned place just a couple of blocks away, so I figured that we'd just walk. Is that okay with you?"

"Sure, that sounds great! Do they have any food cause I'm starving?"

"Yes, they make a thick juicy burger that reminds you of grilling on charcoal."

"Sounds delicious!" I practically bellowed as we headed down the deserted sidewalk. Gerry laughed at my reply as he led me into the busy small tavern.

"Do you want to sit at the bar?" Gerry questioned.

"It seems kind of loud over there. How about a booth over in the corner where it will be easier to talk. I'd really like to get to know you better," I suggested and suddenly realized that it was precisely what I'd say to a woman on a date.

Realizing my embarrassment, Gerry piped in with, "That sounds great! I'd like to get to know you better as well," as he placed his hand on my shoulder in a friendly guy sort of way. He then pulled me toward a corner booth in the furthest corner of the place.

We both slid all the way across our seats as if we were making room for a girlfriend or spouse. We noticed our maneuvers simultaneously and chuckled. "I guess it's just an old habit," I submitted.

"Yeah, we're just a couple of old trained seals. Obedient for life and unable to change."

"I'm afraid that you're probably right about that, Gerry. But, I'd certainly like to be able to try something new."

I was looking at the menu as I made that statement. Raising my eyes afterward, I could swear that I saw a wicked little twinkle in Gerry's eyes. Although he turned quickly to acknowledge the attractive young waitress approaching our table. The thought lingered in my mind as he ordered for himself.

I fleetingly imagined it was Gerry dressed in woman's clothes and bent over the equipment in his shop. I was moving my hands up his thighs and once again shut off the machine. My free hand was now moving above the stockings and caressing his smooth and bare ass. As I moved my second hand up, I began compressing his firm cheeks with both hands. Moving closer to the cleft, I bumped a protrusion with both of my thumbs.

As I attempted to move his g-string, Gerry 'Ahem'd' me rather loudly. Feeling quite flustered at my thoughts and the depth of my daydream, I blushed deeply.  

"Oh, crap. Sorry about that. I just was thinking about something at work for a moment. Okay, I'll have a Miller Lite and a bacon cheeseburger medium with fries."

"Okay, I'll be right back with your drinks," the waitress offered as she turned away.

Still feeling quite disconcerted, I realized that my cock was still very hard, and there was a small wet spot showing in my jeans. Fortunately, no one else could see either. To make doubly sure, I unfolded my napkin and place it on my lap just before the waitress returned with our drinks.

After she delivered our drinks and moved on, Gerry lifted his up to toast. I followed his lead as he submitted, "Here's to the beginning of what I'm sure will be a great friendship."

As our glasses clinked, I added somewhat subconsciously, "And so much more."

Gerry smiled that evil little grin again as we both tilted our glasses back and slurped away. I seemed to be in a constant state of mortification as I replayed my last comment repeatedly in my mind. Attempting to stall my reinvolvement in any sort of conversation, I slowly drained my glass completely. Gerry just watched as my eighteen-ounce beer vanished before his eyes.

I put the glass back on the table and kept my eyes low. After a long pause, Gerry said, "There is no need to feel any embarrassment with me. I'm in the same position as you. We both seem to need a friend that knows what we've gone through and isn't uneasy about talking about it all. I hope that we can be that for each other. I know that I could use a close and understanding friend in my life after all the abuse I've taken at the hands of women."

Trying to lighten the conversation, I burst out with, "So I guess that means that you're not hitting your assistant with the sexy legs?"

"No, I'm not. But, you'd be surprised by what you'd find if you mess with that one."

"Ah, so she's not one to mess with?" I questioned.

"Well, let's just say that I'm sure she'd love the attention but is not everyone's cup of tea."

Just about then, the waitress appeared with our food and another beer for me. Addressing Gerry, she asked, "Would you like another Coke, sir?"

"No, thank you," Gerry replied before she turned and walked away.

The conversation stopped as we both dug into our burgers. I took a few more chugs of my beer to wash down the food that I was inhaling.  

"So, what do you think of the burgers?" Gerry inquired.

Having just taken another bite, I mumbled, "They're yummy."

Gerry started to laugh at my awkward reply, and after gulping down my food, I joined in. We got to snickering so hard that Gerry accidentally knocked his phone off of the table. He bent down to get it but fumbled it in his greasy hands and then couldn't reach it at all.

Sitting back up, he appealed, "Do you think you can reach it? I can't quite get to it, now that I bumped it further toward you."

Wiping my mouth and shaking out my arms like a man to the rescue, I commanded, "Stand back and watch me work." I slipped my head under the tabletop to try and find it. Gerry had managed to drop his phone into the corner on my side. Unable to reach it while still seated, I slid down onto my hands and knees. Upon retrieving it, I promptly bumped my head on the table bottom.

"Are you okay under there?" Gerry asked while stifling a laugh. As I rubbed my noggin, I noticed that Gerry's pants leg seemed awfully short. The reason I noticed was because he wasn't wearing any socks. Upon closer inspection using his phone screen as a light source, I realized that he was actually wearing stockings.

As multiple scenarios raced through my head, Gerry popped his head under the table. "Hey, are you alright?"

"Yeah, just rubbing the knot on my head and trying not to hit it again as I work my way back up."

Upon emerging from the depths, I handed Gerry back his phone. Once settled back in, I promptly went back to working on my burger and fries. It was quiet for the next few minutes as we both enjoyed our meals. In my solitude, I continued to imagine many reasons for Gerry wearing stockings. I knew they were quite common among women and men who stood for long periods in their job, such as me and Gerry.

But then the naughty thoughts came. Maybe that assistant with the great legs was actually Gerry dressed as a woman. After all, he did say that his relationship with her was complicated. Couldn't that mean something more? As my mind dabbled in many possible explanations, I was again brought back to reality.

"Hey, what's running through that busy mind of yours?"

"Just thinking about life and the many twists and turns that it throws our way. If I hadn't moved my office, we'd likely never have met. And I gotta say, that would have been a shame. You already feel like a close friend, and we only met a few days ago. I know that that sounds a bit funny and not in the haha way, but it is true."

"One thing you'll never have to worry about coming from me is judgment. We all have our quirks, myself included, but I try not to live by preconceptions. So, you can tell me anything about yourself or ask me anything."

Testing the waters on his statement, I requested, "So, what's the deal with your leggy helper? You mentioned that your relationship was complicated."

"Yes, it is, but not in the way you might think."

"Very cryptic of you."

"I know. Let's just say that we're close but not in a romantic way."

"Yeah, that's not any clearer. Okay, I'll just put it out there. Do you think she would have minded if I'd have moved in behind her and caressed those legs? And maybe even slid my hard cock into her waiting pucker? After turning off the saw first, of course. I have a thing for anal sex."

Gerry now looked a little flabbergasted as I watched him picturing the scenario in his mind. I assumed that his emotion was about me using his friend in a blatantly sexual manner. Gerry seemed stunned like I had been earlier, so I just drank my beer and watched the gray matter burn. Just before he spoke, Gerry's face turned into that wicked little grin again.

"You know what, I pretty sure that she'd love it. In fact, I'm so confident that I'll set it up for you. But, remember, if you decide to do that, you'll likely get much more than you bargained for. There's always a price to pay for that kind of lustful play. And, don't forget what I said about her not being for everyone."

"So, to sum things up, she's very willing to be used but has some sort of defect that scares most men away?"

"Well, yeah. I guess that's a pretty apt assessment. So, are you still up for taking her?"

"You know, I've been pretty conservative in my life up until now. Especially where my love life is concerned. But I think it's time for me to branch out and try new things. After all, what's the worst that could happen? At the very least, we both have some fun, even if it's only a one-time thing."

"I'm pretty sure that she'd feel the same way."

"Okay then, when will be able to set this up?"

"How about Saturday, early afternoon. Maybe around two? I'll be out running some errands, and she'll be finishing off some work on a big job that we've got going. I'll make sure the door to the shop is unlocked so that you can follow your fantasy of taking her from behind. Just make sure to turn off the saw before you do, please."

"Of course, dismemberment doesn't go too well with my sort of sexual fantasy. So you're sure that she'll be up for this? I'd rather not be arrested for attempted sexual assault."

"Don't worry about that. I guarantee that she'll be more than an eager participant. I happen to know that she loves anal. Someone taking your ass wantingly for no other reason than having nice legs... oh yeah!"

Gerry's eyes closed for a moment as he finished his statement. I swear that he even shivered a little as he blurted the 'oh yeah' at the end. Apparently, he was pretty vested in this whole fantasy, and I wasn't sure exactly why. Did he control her somehow and get off on knowing that she's used like a whore?  

"It seems that you're the one daydreaming now, Gerry."

"Yeah, I was just thinking how much she'll love it and how much it will improve her work performance," he offered as he smiled like a fool.

With my second beer gone and my plate empty, I was feeling a bit tired. I guess that Gerry could see it on my face. "Hey, I think it's time that we call it a night. You look pretty swamped. Are you okay to drive?"

"I'm good, just pretty tired. It's been a long couple of weeks with the move and catching up on all my work. How about I pay this time since I'm the one who made the money today?"

"Okay, but next time is on me."

"I'll definitely take you up on that. Maybe Saturday night after I defile your assistant?" I said while grinning.

"Defile. That's an interesting way to word it. You know that it's not like she's a virgin, right?"

"I know," I replied as I stuffed some cash in the waitress's check folder and stood up. As we moved out the front door, I added, "It's one of those fantasy situations where you get to act out your deepest and most sexually desirable needs. The defilement comes as you use another for your sexual fulfillment without any thought of their needs. But, I'm sure that in the heat of it, I'll take care of her too."

"You better!" Gerry mumbled while turned away from me.  

"What did you say?" I queried.

"Oh, nothing. I was just coughing."

Gerry walked with me to the parking lot, and we shook hands as he offered, "Thanks for the great work on my printing!"

"Thank you for setting me up with your leggy friend," I countered, then added, "Don't forget about Saturday night. I'll want to tell someone about my afternoon romp."

"I won't forget. See you Saturday!" Gerry exclaimed as he slid into his car seat and pulled the door closed.

Neither of us had very far to go. Once I was home, I hit the sack and passed out until the five-thirty alarm. Friday passed by quickly as I still had a backlog to work to complete. Trying to catch up a little, I stayed late into the evening since I'd be off early on Saturday.

Eating a late dinner at home, my mind bounced all over the place, trying to make sense of Gerry's part in all of this. Finally, I surrendered to my body's exhaustion and headed for bed, having made no progress in my thoughts. Saturday morning was busy at the shop. I split time between finishing up some smaller jobs and completing some more billing. In the middle of writing my last invoice, my cell's alarm started to beep. It was one-thirty and time to close up.

I made my rounds making sure all was put away before heading to the car. The drive over left me wondering whether or not I really wanted to do this, but I kept going anyway. Arriving at Gerry's shop, I decided that I'd go inside and apologize for my thoughts and offer to take her out to dinner. Opening the office door, I heard the familiar sound of the equipment running in the backroom.

Approaching the shop door, I saw a note attached that read, 'Jim, please lock the office door before you come inside.'  I turned and did just that without thought before returning to the shop door. Opening the door slowly, it all came back to me in a flood of craving. There she was in her stiletto heels, nude stockings, a short jean skirt, and a thin but form-fitting red sweater. She was standing upright, and I could just make out the bottoms of her stocking tops.

I held my ground while my cock hardened. There would be no apologies and no dinner. I would have her right here in this dusty room, maybe twice. As my lust grew, she leaned forward and exposed the bottom of her bare buttocks. A blazing red lace thong was the only color between her creamy white cheeks. Moving closer, I closed and lock the shop door before turning off the saw.

She began to straighten seemingly to find the cause of the problem when I laid my hands in her plump and inviting bottom. She caught on and bent over fully, which exposed most of her ass to my inquisitive hands. I caressed her backside softly as my cock pulsed heartily, threatening to rip my jeans open. If I was ever going to cum in my pants without being touched, this would be that moment.

As I massaged her fanny, loving the feel of her soft skin, she slowly spread her legs. As her cheeks gradually spread, I saw more and more of her colorful thong. My hands move closer to her cleft when I noticed that she must be wearing a plug. I let my fingers move to the edge of her rear opening and fiddle with the plug. She emitted light moans as I bumped the plug back and forth.

Wanting to please her more, I moved the thong off the plug and began pushing and pulling minutely. The moans increased in volume as I continued to work the plug with one hand while fondling her exposed skin with the other. As I slowly approached the complete withdrawal of the plug, my free hand slipped underneath to her genitalia. It came as little surprise that she was not a she, and it only turned me on more.

I eased my hand to my pocket and retrieved my handy pocket knife. Flipping open the blade, I used both hands to cut her thong in half just above the plug. Putting the knife away, my hands went back to exploring. My movement of the plug had it coming out entirely before plunging back inside. With my other hand, I fondled his scrotum and enlarged cock.

Gerry, I assume, was now panting and grunting as I felt his balls begin to release their load onto the sawdust-covered floor. When his orgasm was finished, I removed the plug and unzipped my jeans. My penis was rigid and coated in my own semen. Between that and the lube that he'd obviously used for the plug, I slid in easily. I only slid about halfway inside for the first few strokes before lust took over.

I was at full depth after a minute and thrusting wildly after another. Feeling the cum begin to rise from my balls, I slammed in full length one last time as I filled his rectum with my spunk. The whole process went by too quickly, but I hoped that it wouldn't be the last time. Slipping from his warmth, I backed up and helped him to stand. He remained facing away from me before I turned him around.

Gerry was in full makeup and looked quite passable, so I kissed him full on the lips. He seemed a bit hesitant at first, but as my tongue entered his mouth, his armor fell away. I held him tight as we ground our soft cocks together. My hands moved back to his ass to squeeze his cheeks and finger his hole. Gerry followed suit, and before long, we were both sporting wood once again.

Gerry made the first move by dropping to his knees and taking me into his mouth. It wasn't long before his middle finger was two knuckles deep within me. My cock was hitting the back of his throat with every thrust. Soon after, I was exploding into his talented mouth. After licking me clean, Gerry stood, and we kissed some more.

Wanting to return the favor, I dropped down and took him into my mouth. It was my first time, but I loved the feel of the soft, smooth skin wrapped around such rigidity. I pushed his legs apart and cupped his scrotum with one hand while slipping two fingers into his ass with the other. What I lacked in sucking skills was made up for by the plunging of my fingers.

As he closed in on his second climax, I began to get more and more of his semen and loved the taste. When his sac tightened, and his cum came, I kept it in my mouth to enjoy the flavor. Finally swallowing it all, I licked and sucked him clean before standing to kiss him some more. We finally pulled apart, and I zipped up.

Looking at him for a moment, I suggested, "Why don't you go touch up your makeup and put on some new panties? You still owe me dinner tonight so that I can tell you how much fun I had with your assistant."

Walking toward the back door of his shop, Gerry turned and added, "You also owe me a new pair of panties."