Try This on for Size

Try this on for Size

It was the summer before my senior year of college. I was staying in the city to take a couple of summer classes, instead of going home to work in my family’s hardware store. If I got these classes out of the way, my last semester would be a lot easier. I had been working at the “Endzone Sports Bar and Grill” for the last year and a half. During the school year I mostly worked weekends, but this summer I was working several weeknights. I was the bartender, there was a cook and his assistant, a server and the manager working on weeknights. The manager was great to work for, she had been working there for more than 5 years, about the same amount of time as the cook. The assistant and server were college students like me and we all started within a month of each other. We got along well, and work was actually fun most nights. On the weekends we would be much busier, and we would have an additional bartender, server and cook, the manager would also help behind the bar. The bar was open until 1 AM, the kitchen would stop serving at 10 PM, we would have to clean and stock everything for the next shift, and I would usually get to leave at 2 AM. If there were no customers after 11, we would be allowed to close early.

It was a Tuesday night in July, we had a good mix of drinkers and those coming in to eat. The last people ordering food had finished eating by 9:30 and the cooks had started their cleaning. Our regulars were seated at the bar and Jen, the server, and I were laughing and joking with them, as we always did. Cindy, the manager, was in the office doing some paperwork. By 11, Bob and Carla, the cook and assistant, joined our regulars at the bar and I got them each a drink. Our last three regulars left about 20 minutes later. There was still a couple sitting at a table in the corner. Jen and I started to call them Travis Kelse and Taylor Swift because they were just staring at each other all googly eyed in love. They were just nursing their beers and just oblivious to anything around them. If they would finish up, we could all go home for the night. Jen had gone to their table every 15 minutes to see if they needed anything else, they barely acknowledged her as they continued to stare into each other’s eyes. I would laugh every time Jen would turn away from them and roll her eyes, open her mouth, and poke her finger down her throat in a gagging gesture. At a little after midnight, we started shutting some of the dozen TVs off that were scattered around the bar. They still weren’t taking the hint. Finally, at 12:45, I announced, “last call”, this seemed to bring them back to reality. They looked around the empty bar and quickly downed their beer and left. I had the entire bar area cleaned and stocked, I just needed to wash their glasses and I would be ready to leave. Cindy came out of her office and laughed, “did Travis and Taylor finally leave?” She locked the front door, and we helped Jen finish cleaning the tables and put the chairs up. We also helped her sweep and vacuum the floor.

The temps had reached the nineties today, so once we had our cleaning done, we went to the bathroom and changed from the sweaty striped ref’s shirt and dress pants that we wore for our uniform, I changed into a pair of kaki cargo shorts, t-shirt, and flip flops. I decided to take my sweaty underwear off too and free ball on the drive home, it would be a lot cooler. We all walked to our cars together, something we started when one of the other servers was scared by an ex-boyfriend waiting for her one night, also because Cindy had the daily receipts with her. I looked at the clock in my car as I pulled out of the parking lot, it was 2:17.

My girlfriend had broken up with me right after we got back from Christmas break last January. We had started dating in our freshman year, and all of the sudden, she needed some alone time, or was trying to find herself, or some other bullshit. By Valentines Day, she was with another guy, so evidently it didn’t take her long to find herself. It didn’t bother me too much, the relationship had run its course and if she hadn’t ended things when she did, I probably would have before too much longer. As a result, the only action I had seen in the last six months was with Rosy Palmer and her five sisters.

The street I drove to get home took me past a strip mall. At this time of night, the only business that was open was an adult novelty shop. I had been in the store a couple of times before, when I was still with my girlfriend. We stopped in to buy a lace teddy for her to wear on a weekend trip we were taking. The store was set up with all the lingerie displayed in the area that could be seen through the front windows. Behind that was all the sex toys, videos, and magazines. It had been so long since I had been laid, and my hand was becoming quite boring, so, I decided to stop and see what they had in the way of a pocket pussy or a fleshlight. I had heard a couple of my buddies talking about them and it certainly sounded better than spending the night with internet porn and a bottle of hand lotion. The parking lot was empty, so I figured it would be a good time to stop and not be embarrassed by making such a purchase with a lot of other people being in the store.

A buzzer signaled my entrance, I saw the lone employee sitting behind the counter. He looked up from the book he was reading and smiled, “hi, how’s it going? Let me know if you need any help finding anything.”

I kept my head down as I walked by and gave him the reply, I am sure he has heard 1000 times, “oh, I’m just looking, thanks.”

He went back to his book, he appeared to be a college student, the book looked like a textbook. I glanced back at him as I walked around the store, I noticed that he was very good-looking. He was about my age, had very short, cropped black hair and his perfect white teeth were in direct contrast to his smooth ebony skin. I made my way through the teddies, underwear, and nighties, I walked around the corner and looked at a couple magazines, them some videos. The store clerk was still studying his book, so I continued looking around. I turned to see a wall filled with dildos, every size and color imaginable. I chuckled to myself, I don’t think I would want to meet the women who could take the huge one in the center of the wall, it had to be almost 20 inches long and 6 inches in diameter. There were lotions and lubes lined in perfect rows on the shelves next to the dildos, some scented, water based, oil based, man, I had no idea there were so many options. Finally, I saw what I was looking for, again, I was overwhelmed with the number of choices. Some were simple and plain, some had vibrators in them, and again, there dozens of sizes and colors. I pulled one off the peg hook to give it a closer look, the package had an opening so that you could feel the texture of the material. I hung it back up and was taking the next one, when I heard, “have you found one you like?” I nearly dropped the package as I turned to see the black adonis that had been sitting behind the counter, smiling at me. He apologized, “I’m sorry, I didn’t mean to startle you.”

I blushed, “that’s ok, I was just… well, there are so many options.”

He chuckled, “yeah, there are. Maybe I can help you narrow it down. This section is a vinyl material, this section is latex, and here we have my favorite, silicone.” For the next five minutes, he explained the differences, giving me the details on each material. I stood there in awe of his knowledge and professionalism, it was like I was at Best Buy, and he was telling me all about the latest laptops there on display. I really didn’t hear a word he was saying, I was too busy staring at him. He was about 5’8”, 140 pounds, just a couple inches shorter and 20 pounds smaller than I was. He was wearing a purple polo shirt with the store logo on one side and a name tag that said “Troy” on the other. I looked down further, he had on black shorts, a pair of white Nikes, and had smooth, muscular calves. He continued to talk about the products that were displayed in front of us.

He said, “now this one is ribbed, we also have one with little nobs inside, they each kind have a different feel.” He smiled, “I have to admit, I kind of prefer the ribbed myself.”

I couldn’t believe that I was standing there with a complete stranger talking about jacking off.

He continued, “now this section has the larger toys, for those that are more well-endowed.”

I felt myself blush, he noticed and paused before he said, “oh, I didn’t mean to make you uncomfortable, you of course, can choose the size you need.”

I swallowed hard and noticed that my dick had indeed began to swell.

Troy turned back to the display, “this one has a vibrator built in, it’s rechargeable so you won’t need batteries. And this one actually strokes up and down the penis and is virtually hands free.”

I laughed, “shit, I would never have to find a girlfriend if I had that.”

He laughed too, “yeah, they make about anything these days.” He paused as he looked me over again, and I felt my face heat up once again. I noticed his eyes stopped at my crotch, I suddenly became aware of the fact that my cock was now fully hard and pushing against my shorts. I looked down and saw the wet spot that had appeared.

Troy smiled at me, “it looks like definitely don’t need the small size, would you like to try this one?”

He pulled a package from the wall and opened it up. He handed me the silicone masturbation device and said, “go ahead, put your finger inside this and see how real it feels.”

Am I really doing this? Am I really discussing something so personal with someone I have just met?

I slowly take the item, and just as Troy instructed me, I stick my finger inside. It was soft and fleshy, and I could feel the ribs on the sides, I was sure Troy was right, this would feel good rubbing on my cock. I swallowed hard as looked back at Troy.

He smiled as he licked his lips and looked around the store, he said, “maybe you would like to see how it feels.”

I croaked out, “what do you mean?”

He grinned as he ran his hand along my hard-on, he said, “you seem to be a little excited and by the size of the wet spot on your shorts, I think you could use some relief.”

I looked down as he unbuttoned my shorts and my cock jumped out. My shorts fell to floor, leaving me fully exposed to Troy and anyone else that would happen into the store. He rubbed his finger across the leaking head of my cock and smeared my precum on my shaft. He took the silicone pocket pussy from my hand, spit into the opening and slid my dick inside. I sighed as Troy slid the silicone down the entire length of my manhood. He smiled at me as he started to pull back and forth, holy shit, Troy was right, the ribs were incredible, and he knew just how to squeeze at the right times.

He smiled at me and asked, “how does that feel?”

I panted, “good.”

He asked, “does it feel like a real mouth?”

I nodded, “yeah, sort of.”

He grinned and said, “maybe we should let you compare the toy to the real thing.”

Before I could comprehend what, he meant, Troy pulled the silicone from my cock and fell to his knees and took my dick into his mouth. I gasped as my knees buckled, I steadied myself by placing my hands on his shoulders. I didn’t stop him, I just looked down as he bobbed up and down then switched back to the toy, then back to his mouth, over and over again. He gave me the best blow job I had ever gotten in my entire life. It damn sure was a better sucking than any girl had ever given me. Troy began to massage my nuts as he continued to suck my cock, he felt them start to tighten and my breathing quicken. He abruptly let my dick fall from his mouth as he stood up and kissed my full on the lips. My head was spinning and without thinking, I kissed him back, for a good five minutes.

He stepped back with a big smile, “that was nice, let’s try another toy.”

Before I could answer, he turned back to the rack and pulled another package from the display. He ripped open the package and gave it a couple tugs, stretching it out. It was about twice as long as the last toy, it was a see-through purple color, and I could see little nobs inside on one end. Troy smiled as he took my cock and guided it into the toy. Again, he was right, the nobs gave my dick a completely different sensation than the ribs of the last toy. Our eyes were locked on each other as he worked the toy back and forth on my cock. I dropped my gaze and noticed that my dick was only filling about half of the toy, I looked back up at Troy, he said, “this one is more fun with a friend.” He stepped back a little and unbuttoned his shorts and let them fall to the floor. He moved directly in front of me as I looked down at his rock-hard ebony cock standing proud of trimmed black bush, his full nuts hanging low against his thighs. He stepped in closer and fed his dick into the other end of the toy he was stroking my cock with. My eyes went wide as I watched his cock inch further into the see-through toy until his dickhead touched mine.

Troy leaned in and we kissed as he worked the toy back and forth on our stiff poles. He broke our kiss and stepped in closer, his cock was now on top of mine and the silicone stretched to accommodate the thickness of both of our dicks. I had never touched another man’s cock, let alone rubbed my own cock against one. Troy once again stopped stroking just before I was ready to cum, he removed our dicks from the toy and turned back the display and grabbed another package. He turned back to me as he opened it and said, “this one feels just like fucking a tight ass.” He took a bottle of lube from the shelf next to the display and squirted the contents on my dick and new toy. He guided my cock inside and smiled at me as he worked my dick in and out of the tight hole. He had moved to my side, and he had his still hard cock pushed against my leg, I put my arm around him as he worked the toy up and down my shaft.

He asked, “does it feel like a real ass?”

I said, “I have never fucked an ass before.”

He chuckled, “ok, we need to change that, right now.”

He pulled the toy from my cock and squirt some lube into his hand and spread it all over his ass crack. He pulled me to the floor and got on his hands and knees in front of me. He looked over his shoulder and winked, “give me that cock, big boy.” He had me under his spell, I slowly moved forward until my cock was pointed at his waiting hole. He gave me one more look over his shoulder as I pushed in past the first ring of muscle. I paused to allow him time to adjust to my dick, then pushed in until I was balls deep in his warm tight ass. The toy felt great, but Troy’s ass was incredible. He moaned as I started to push in and out, he was soon pushing back and we got into a steady rhythm. I felt that familiar tingling and balls tighten, I knew I was getting close.

I panted, “I’m going to cum.”

He pushed back tight against me and said, “fill me with your seed, stud.”

I probably wouldn’t have had time to pull out anyway, I exploded with what felt like biggest load I had ever shot in my life. Troy also spilled his seed on the floor below him. We fell forward, with me still embedded in his hole and tried to catch our breath. Once my shrinking cock fell from his cum slickened hole, I fell to the floor beside Troy. He smiled as he came to me for another round of kissing.

He asked, “what was better, my ass, or the toy?”

I chuckled, “definitely your ass.”

He gave me another quick kiss, “yep, the toys are ok to get you by, but there is no substitute for the real thing.”

I’m not sure where they came from, but Troy had a roll of paper towels in one hand and was cleaning the cum he had shot on the floor with the other. He gave me a few towels and I cleaned my dick as we both started to pull our shorts back on.

We chuckled as we gathered up all the “samples”, walked to the front counter and I pulled out my debit card.

He smiled, “you don’t have buy anything you don’t want.”

I smiled back, “I’ll take everything, thanks.”

He handed me the bag of goodies and I walked toward the door, just as another couple walked in.

He cheerfully said, “thank you sir, please come again.” I grinned at him as he turned his attention to the new customers, “hi folks, please let me know if you need help finding anything.”

I set the bag on the passenger seat next to me as I started my car. I laughed to myself as I looked at the bag that had just cost me over $100, “either Troy is the world’s best salesman, or I am the biggest push over to ever walk into that store.”

 

The End.