My First Time Pt. 1 – The Boss makes his move

I was stocking boxes in the warehouse at plastics company. This was my after school job, at 18, not bad at $10 and hour.
My boss, Bob walked in behind me. I could hear him fumbling around, moving boxes. He was always in and out, so I didn't really care.
I didn't look back b/c i just wanted to get my work done and go home.
I knocked down a couple boxes which spilled some of the box filler, I was so fucking embarrassed. But hey shit happens even when it's bad timing.
I instantly dropped to my knees trying to scoop them into the boxes before Bob said anything.
I was wearing tight jeans and a company t-shirt, it was a bit form fitting, so when i bent over my lower back would show including the top of my ass crack.
Before I could get two handfuls into the box I heard Bob mumble something under his breath.. I looked back quickly at him and immediately said “my bad, so sorry Bob, nothing broken!”
He said in his scratchy deep voice, “No problem Adam, nice view” and walked out. I immediately grabbed for my shirt and I pulled it down. While doing so I was quickly reminded that I had slipped on a pair of my s****rs panties that morning, so I stood up as fast as I could. “fuck” i whispered…

I was embarrassed, that's all I could think of the rest of the day. What the hell, if he says anything or tells anyone I'll flipping die!!!!

I first started wearing panties when I was 14, more of a experiment than anything else. Stealing my friends Mom's and s****rs undies from their laundry baskets. But through the years I became more interested in wearing other stuff like stockings, garters and full lingerie. Online ordering became the easy way for me. I'd typically hide them in an storage box in the back of our garage. And when my parents and s****r were gone I'd put them on. It was a rush, fantasizing about being with men. I had purchased a few lifelike dildos online, only 6″ though and not too thick, and had over time trained myself to take the entire toy cock in me. It was a thrill to me. But of course the f****y was never gone so I had resulted to occasionally slipping into a pair of my s*s's panties. Late at night I would sneak my toy lifelike cock out, slip on a pair of panties and fantasize about being fucked by a big mature man. I was attracted to older men, especially guys that would be considered very hairy. The first cock I ever saw was my Uncle Larry's, it was big and hairy. I watched him pee while camping and too me it was so sexy.

I bolted out the door from work that day, not making eye contact with anyone. I was embarrassed, so embarrassed my s****r asked me what was up when she picked me up from work. I just redirected her and asked her how her day was. When I got home I ate, did my homework, said good night and headed for bed. What Bob said was on my mind. What the fuck did he mean..”nice view” – “who the fuck does he think he is?” I put my pajamas over my panties and headed for bed.

Bob was a married overweight 55 year old man. The warehouse constantly made fun of him for being overweight. He stood about 6-0 and easily weighed 225 lbs. His belly poked over his belt a bit, but not too much. He was a hairy guy for sure as well, he was constantly scruffy but you could tell he had to shave his neck often. His chest hair would stick above his collar and was dark with some mixed gray and his forearms matched. He was serious guy, would joke around a bit, but a good guy as well. In my curiosity I had checked out Bob, looking him up and down. Trying to get glimpse of him in the bathroom. When he would have his team meetings he would sit in front of the team and I would constantly glance at his crotch, wondering if his cocked looked like my Uncles.

I slid under the covers mad and confused, but let out a laugh. What a crack up! What if Bob was actually flirting with me? Holy Shit! No Way! I entertained the thought that night and ended up sliding my pj's off, grabbing my toy and fantasizing about Bob rubbing his big hands on me, pinching my nipples, grabbing the inside of my thighs and working his way to my ass. I slid a few fingers with lube and then worked my toy in. Picturing Bob at the end of my bed with his hands holding my legs up and sliding his cock in and out of me. I stuck the dildo to my headboard and fucked it like I never had before, ending in a loud whimper and massive cum shot and then collapsing on the bed.

That morning before school I decided to wear jeans that weren't so tight and normal boxer style underwear to spare potential embarrassment at work. School ended and I headed to work. What the hell could the day have in store for me.

It was the Holiday's and so the company Christmas party was that coming Friday. The Christmas decorations were everywhere in the office and warehouse. Last years party was a great time so I was looking forward to this one too. My buddy Joey in the warehouse told me he was bringing some booze this year. He and I would sneak out and drink all the time so I was up for it.

I had to make a few copies of our shipping slips so I headed into the main office. I knew I would pass Bob at some point, but I was ready for it. And really didn't give a shit. I had about 20 or 30 copies to make so it had my full attention. “There he is!” Bob chuckled as he entered the printer room. “How's it going Adam?” “I'm good, you Bob?” I responded. “I'm good Adam too, ahh you changed your look, that's too bad” he laughed, “Pink is your color.” he yelled before exiting. I quickly jumped to the hallway to confront him. Okay, now I know he knows and I know somethings up! He had closed his door to meet with our CEO before I could say anything to him. “DAMN IT!” I thought.

I didn't see Bob at all the rest of the day, so before heading home Joey and I made plans on how we'd sneak booze into the party, so I agreed and told him I'd see him in a few nights.
I had a few big tests over the next few days so a day off would serve me well. As soon as I got home I ate, studied but before going to bed I headed to the garage and grabbed my special box.
When everyone was asl**p I dressed in stockings, garter and my favorite panties. I pulled a t-shirt tight exposing my belly and looked at myself in the mirror. I have a thin build, long legs and kind of a perky ass. What very little hair I have I've shaved to make my dressing experiences feel more feminine. I slowly rubbed my hands on chest and ass, squeezing my cheeks and spreading them just enough to see my hole. I couldn't stop thinking about what Bob said and what this would really feel like if it were him doing this. I positioned my dildo so I could ride it watching my limp cock bounce around and then eventually becoming hard, I was whispering “yes Bob, do me” “mmmm yess baby take me” and eventually spurting all over my bedroom floor, imagining Bob cumming in me as well.

A few days past, and it was Friday the company Holiday party. My s****r dropped me off at the party and told me to give her a call when I needed to her to pick me up. Joey was already there with a big smile, so we headed to the warehouse and drank a few shots laughing about school and just having a good time. I had put on a pair of my s****rs newest victoria secrets panties which felt amazing to me. Joey and I headed to the party in great spirits mingling and having a great time with the others. Bob came a bit late too with his wife and was introducing her to the company. He made his way over to us, said hello, made a quick introduction and walked away. Just as he walked away he looked back at me quickly, viewing me from head to toe with a little smirk. Joey quickly looked at me and said “what the fuck! what an asshole! what a weird look!” Joey and I grabbed some punch and poured the rest of his vodka into the two cups. We were both buzzed at this point and having a great night. Bob had already left with his wife but said he would be heading back to make sure the warehouse and office's were locked up. We didn't think anything of it, but both Joey and I knew we were closing the party down. It was about 12 am and Bob was back telling everyone to head home. In the nice guy tone he asked if everyone was okay to drive, if not he'd be happy to give them a ride. Joey took him up on his offer, so I quickly texted my s****r and told her I'd be joining Joey and Bob. Beside this would give me a chance to hang with Bob a bit more to see what he had meant by all of these weird comments to me. Bob locked up, loaded up his SUV with a few others along with Joey and myself and headed out. The drive was quiet for most of the trip and based on the direction he was taking it looked like I'd be the last dropped off. As Joey jumped out of the car Bob yelled hey Adam jump in front. I was in the third row of seats sitting uncomfortably so I jumped at the chance for comfort and yelled “Later Joey!”

I was last to be dropped. We hit a red light and there was total silence with the exception of a faint holiday song on his radio. Keeping his eyes on the road Bob started a conversation about work and how it was going. I played it cool and kept the conversation going. He then asked how much I had been drinking, I just chuckled and said “O'well you know Joey, always fun”. He laughed back and said, “hey let me ask you something” “Uh okay.” I responded. “you curious about my comments at all?” he asked. “Yes of course! I do Bob, Holy shit haha” I yelled d***kenly.

Bob: “Well let me ask can I see them again Adam?” Bob looked at me just as the light turned green.
Me: “I said hey go, it's green..what do you mean?”
Bob: “Well I know you wear panties Adam, I think they're great, actually really sexy, so I thought I'd ask if I could see them. I promise not to share this with anyone, really, so what do you think?”
Me: “Ya well Bob, sorry to tell you they weren't panties, I mean c'mon really”
Bob: “Adam, the VS, for Victoria Secrets tag and not to mention my wife has the same pair was a dead giveway..ha ha” “nice try”
Me: “Well okay, ya they were but I mean I just tried them once”

We went back and forth for 5 minutes of me denying it to the point I finally admitted it. Bob had pulled over a few houses before my house without me realizing to continue the conversation.

Bob: “C'mon Adam, can I see them now?”
Me: nervously I said “okay, just quickly”

I glanced at Bob's crotch that looked big and plump, I knew something under was stirring, it just looked bigger. My nerves had kicked in as I leaned forward and raised my shirt to show him.

Bob: Can't really see it, do you mind raising up a bit so the street light shines on them?
Me: Oh, Sure

I looked over at Bob as he looked my lower back and panties over. Bob's hand moved from the center console and rubbed my back brushing my hand, he gave it a gentle squeeze.

Bob: Can I touch them.
Me: What? Oh man..uh I don't know. (my teeth chattering) ya sure I guess I giggled..

His hand was already on my back before saying yes and it was rubbing my back gently as it moved down to my waist line and onto my panties. I raised my ass up a little.

Bob: Yes I like that Adam, I've always had my eye on you.

His hand moved away from my tight waistline and onto my ass, sliding in between my cheeks just a bit, he have them a nice squeeze and little pat.

Bob: mmm he groaned.

I looked over and Bob was grabbing his glorious bulge. It looked more than a handful, it looked thick even in his hands. He grabbed my hand and put it on his leg and then moved it onto the bulge he had been stirring. As my hand met his clothed cock it didn't disappoint, it was thick and growing fast. Bob looked me in the eyes.

Bob: So nice Adam, can I see a full view now?

I raised my ass and eased out of my jeans leaving my panties on. I leaned forward to not lose the momentum i had made on his covered cock. His hand met my bare ass with an instant warm grab of my cheek. I turned around for him to show him the full view. “o'my how hot are you! wow adam” bob whispered. Bob was rubbing my ass cheeks commenting on them and asking me to not move. He told me he would remember this moment forever and that I had the best ass he'd ever seen. I was so fucking hot I believed him. Haha. My mind was locked on seeing Bob's cock in the flesh, so I slowly moved my hips so that Bob could still play and I could still see and maybe put my hand back on it. As i turned I found Bob with his cock fully exposed. He was easily 8 inches with a full base of pubic hair adding to it's beauty. His cock had some discoloration. He was part italian, so his skin had a darker tone. It was beautiful. “oh shit how hot bob” i responded. “you like adam, have you ever sucked a cock before?” he asked. “No, other than a toy one I have at home” I said. “Would you like to try?” He asked. As my hand touched it live chills shot throughout my body. I was instantly hard now myself and couldn't believe what was happening.