Secret Surprise

I go to work each day in a suit and tie and do my job to the best of its ability. It’s a mundane job and I get very little pleasure form my work. I do enjoy the office environment and there is this one guy, Preston, that catches my eye each day. He is a Senior Trader, like me, and dresses to the nine’s: custom suits, tailored shirts, powerful ties and polished shoes. We are pretty good friends and have known each other since he started 8 months ago.

We will sometimes head out for drinks after work and talk shop and that leads us to our personal lives. I enjoy our conversations and especially when we get to have drinks together.

After a Friday at work, we decided to head over the Sapphire, a new bar in the South End of town and drink our stress away. I ordered a Peroni and Preston ordered a Makers Mark, neat. We enjoyed our cocktails and I began by saying, “Shit day today, eh?” And he replied, “Yeah, these are the days bourbon was made for.” I said, “Let’s not talk about work. What plans do you have this weekend?”

Preston was new to the city and said, “Not much, I don’t really know my way around the city yet and its so cold, I will probably just hang in. How about you?” I said, “I don’t have many plans this weekend. The winter is cold and nasty so I will probably run a few errands and pick up around the house.” He asked, “Want to hang tomorrow evening? We can grab take out, or go out for drinks, whatever?”

I said, “Sure, lets meet at your place around 5?” He said, “Sure, sounds good.” And we continued to have a few drinks as the stress of the day seemed to linger on. We chit chatted about various topics and were beginning to feel a little drunk. I said I was going to grab and Uber and Preston asked if he could split it with me.

As I got out of my bar seat, I kinda rubbed up against him and he reached out and “kinda” brushed his hand near my cock. I didn’t think too much of it since it was so crowed in there and I headed to the Uber. Preston right behind.

We got into the Uber and he said, “I just noticed how nice your ass looks in those pants. I also liked the little touch of your cock that I got when you got out of your bar seat.” “Ahh, so that was on purpose? I thought it was an accident.”

“No Tim, that was a shameless attempt to see if you noticed or had any interest,” said Preston. “Well, I wasn’t sure so I played it cool but glad you have interest as well. I have admired you since you started and glad we became friends.” I said.

I leaned into him and gave him a kiss. He accepted and the Uber driver rolled his eyes. We arrived at my place a few moments later and I said, “Well, see you tomorrow, right?” Preston responded, “If it has to be tomorrow I guess that’s okay but I was hoping to spend more time with you tonight.” I said, “Well, I have no booze and need to pick up a bit but if you don’t mind, you can run around the block and grab a few beers and a bottle of Maker’s at the liquor store around the corner while I pick up a bit?” Preston jumped out of the car, pecked my on the cheek and said, “What apartment?” I said, “Buzz 16B and I will let you in the door.”

I ran upstairs and picked everything of clutter and threw it in a nearby closet. I keep my place pretty tidy due to my OCD so there wasn’t much to clean up. I heard the buzzer and let Preston in. A few minutes later he was at my door.

“Wow, this place is great!”, he said as he saw the floor to ceiling glass that overlooked the sparkling city lights below. “Thanks”, I said. We cracked open a Peroni and went to the couch and turned on the hockey game. It wasn’t long before he was inches away from me and we were making out. We would come up for air every now and then and sip our beers. Preston reached for my cock and began to rub against it with his palm. I leaned back on my couch and he followed me, laying off to the side so he could continue to rub my cock. I spread my legs allowing him full access and enjoyed my cock getting hard.

I pushed him back and stood up. Preston followed and we swayed back and forth. I began unbuttoning his shirt and exposed a nice wife beater. He was very toned and his pec’s bulged from the shirt. I undid his belt and undid the button an zipper and his pants fell down to the ground exposing a nice pair of light blue Calvin Klein Black trunks, a nice bulge in the front showed me he was also growing with desire. Preston stepped back, pulled his polished loafers off his feet and stepped out of his pants. He leaned down and removed his socks. I said, “Wow, I wasn’t sure what unwrapping you would look like but I like it!”

He stepped closer to me and kissed me, fumbling with the buttons of my shirt but working his way, he pulls it back and exposes a white satin camisole with navy blue bra straps. Preston embraces me and rubs my back through the shiny satin cami and comes in for a kiss. He pulls the camisole over my head and steps back and says, “Damn Tim, I love the bra! I had no idea you were into that stuff.” And returns with a kiss and a press of his hand against my breast through lace bra. I am turned on now and my nipples perk up. Preston removes my bra and sucks on my nipples while working to undo my belt and pants. Successful, my pants slide to my loafers and expose a navy lace garter belt that is holding up black stockings and navy satin and lace hipster panties.

He falls back onto the couch and just stares at me for a bit. “You know how to turn a guy on!”, he says and motions for me to come meet him on the couch. I straddle him and my panties grind into his Calvin’s, our swords growing with the friction. Preston is rubbing my ass with both hands and I can tell he loves the satiny feel of my panties.

I reach down while making out with him and grab his cock. He is quite big, like 8 inches and his cock is rock hard now. I slide back off the couch and kneel in front of him as he moves to the edge. I work my tongue upward from his knees, licking along the way. I pull his underwear down and unwrap a well groomed area. Pubic hair trimmed very short and in the shape of a rainbow just above his cock and his cock and balls are hairless. Perfect, I think! I love well groomed men. I work my way up and take him inside my mouth. To the base of his cock, I almost choke on it before retreating back to the tip where I stroke his cock while sucking the tip and swirl my tongue around the tip. Preston leans back, enjoying the pleasure I am giving him. I am enjoying it as well and lower my mouth down every so often to keep his shaft wet and roll my eyes up to catch Preston’s eyes closed and his hands rubbing my hair, occasionally pushing me down when he wants to feel my tongue on a deeper part of his cock.

I pull back, and while stroking his slick shaft, I ask, “Want to move this to the bedroom?” Preston nods yes and I get up and lead him by his cock into my bedroom. He taps my ass and says, “Damn, your ass looks amazing in those panties!”

On the bed, we get a bit more adventurous thanks to the added space provided by a king bed. I start sucking him off again and as I do, Preston pulls my leg toward him and before long, I am sucking him off while I am hanging my panties over his face. He pushes upward with his face and begins grinding his face into my panties. His mouth open and rubbing my shaft through the satin. I am growing hard and the tip of my cock pokes through the top of my satin and lace panties.

I am enjoying this as I am sucking his cock and before long, he has pulled my panties to the side and taken me into his mouth. Sucking my cock and balls, also bare from my recent waxing, and milking me, Preston is enjoying me as much as I am enjoying him.

I stop for a moment and look backward at Preston and ask him, “Can you finger my ass?” And within a second, he has a finger up there, prepping the anus for penetration. I am moaning softly but increase the noise level when he gets. A finger inside of me. I push back against him and invite him deeper into me.

I go back to work on Preston’s knob and enjoy the sexual energy I am feeling. I feel Preston’s balls tighten and I feel his cock release a thick creamy load into my mouth. I feel him go limp in my mouth as I clean him up and I swallow his all of his load.

I climb off of him and reach for my end table and pull out a Rabbit Vibrator. Preston is in post climax ecstasy enjoying the glow when I show him the vibrator and turn it on. I lube up the vibrator and lean back to insert it into my ass and place the rabbit ears against my scrotum. I turn it on and move it in and out slowly with one hand while jerking off with the other. Preston rolls to his side and kisses me which rubbing my nipples and every nerve ending is being taken care of at the moment, I arch my back and pull my knees upward, enjoying the ball bearing spin action of the vibrator in my ass.

Preston heads to my cock and begins blowing me. Taking me to the base and slowly sliding upward to the tip. Swirling his tongue along the way, he takes the vibrator from me and and my hands are free to stroke his hair. The vibrator working me into an euphoric state I pull Prestons; head away and release my load all over my stomach and chest. My cock pumping and pumping sticky loads of cum all over my garter belt, stomach and chest.

Preston removes the vibrator from my ass and watches my hole pucker as I empty myself. My cock goes flaccid and and slides out of Preston’s hand. He climbs on top of me and we kiss deeply while my cum glues us together for a moment. He retreats downward and licks me off of my stomach, lapping the pool of cum from my belly button. I flop him over on his back and do the same to him, savoring my man goo.

I crawl on top of him and we kiss again. Swapping the last remnants of my cum back and forth as our tongues collide and my satin panties grinding against his cock gets him hard again, and I say, “Should we hold round two for tomorrow?” And Preston responds, “No, you look so fucking hot with that vibrator, I want a turn. Do you have an extra garter belt and panty hose? I want to try that as you were so fucking hot!”

And with that, our weekend was filled with fun and adventure and multiple orgasms. And, I managed to turn Preston on to wearing women’s panties. I cannot wait to be back in the office thinking of him in that sexy attire under his suits!