If you read the previous story, you know about my online trysts with Derek during the Covid work-at-home era. At the time, I rationalized this would let me have some fun without returning to my cheating in real life. I had been trying to get my act together and be faithful for a few years. But the return to the office led to opportunities for IRL meetings that were impossible to resist. But before we could act on that, we were twice frustrated, once by my being promoted to become his boss, and a year later, as he was being rotated to the west coast and given a new boss. We could finally plan a rendezvous during in his last week in town. But that fell apart when, just before his move, I came down with Covid.
Four years later, last fall, our company decided to design a completely new first-class airliner seat. They scheduled a two-week January design kickoff, bringing scattered project participants to their Chicago office to outline the project’s features and project plan. Our group had the metal and composite parts. Manufacturing, the cushions group, and electronics were also coming. If found out that Derek would represent electronics.
I was excited. With a wet pussy, I replayed memories of our online fun whenever I had a private moment. Would it finally happen? Did he still want it?
Derek and I had stayed in touch. We even continued our online trysts for a few weeks, with him sitting on boxes in his new apartment. But that lost its appeal and we stopped. With my resistance down, I took up with George and Sean. I told you about that in other stories. Derek found a new girlfriend, Beth. They were engaged, so any possibility of a liaison was left to “We’ll see.”
Still, I had to prepare. I bought a new red thong and tiny matching bra. I shared them with Arthur, my hubby, on Christmas morning and a few other times, just to avoid arousing suspicion. I stuffed them into a secret compartment in my luggage and headed to Chicago.
Everybody arrived on Sunday. That night, we gathered behind the restaurant in our Embassy Suites hotel. I put on the old blouse I had worn the first time we logged onto Skype, along with the new thong and bra. Instead of pajama bottoms, I wore baggy pants to convey the memory.
The VP in charge of the project introduced us to each other, mostly in pairs. “I believe you know Derek. He’s leading IT,” he said, “pretty impressive.”
“He was impressive before you stole him from my group,” I replied with a chuckle. Offering my hand and trying to be as professional as possible, I added, “Good to see you again, Derek. I hear you’re making waves on the west coast. Congratulations on your engagement.” Derek’s handshake managed to convey the message I was hoping for.
We had a moment together picking out hors d’oeuvres. As I leaned over the table giving him an opportunity to peek down my cleavage, I told him my room number, “… in case you want to chat and catch up on things.” The ambiguity of “catch up on things” was intentional.
As you may know, the suites at some of the older Embassy Suites have two rooms, a bedroom with one or two beds in back and a living room/kitchenette/bar in front with a pullout sofa. At the appointed time, I pulled the curtains on the windows facing the hallway and left the door ajar. I had changed to pajama bottoms in memory of our first online date. Then I stood back with my elbow and two glasses of champagne on the bar. Would this just be a chat” Or something more?
Derek slipped in and stared at me, “Wow!” Then he walked up to me, threw his arms around me and started kissing.
I broke off and said, “You’re engaged now, Derek. Are you sure?”
“And you’re married. We’ve wanted this for years.” We kissed for several minutes, tongues playing. He moaned when I sucked on his tongue. I moaned when his hands cupped my breasts.
With a free hand, I handed him one of the glasses. “Why don’t you sit on the sofa?”
He did as asked. “It’s nice to see the whole Candy. In person this time. I gotta see what’s under those clothes.”
“I suppose you want me to strip,” I said, wondering if he remembered when I first said that.
“Wouldn’t that be fun,” he replied as he chucked the champaign.
I had made him undress in unison back then, but I decided to go solo this evening. I slowly unbuttoned my blouse, revealing more cleavage and my little sheer red bra.
“Such a pretty bra!” he remarked.
“Well, you already saw it, downstairs,” I quipped. “I caught you peeking.”
“Guilty, but not like you were hiding it at the snack table. I could practically see your belly button. Just not your nipples.”
“Well, maybe we can do something about that.” While holding the blouse apart, my thumbs tugged the edge of the bra down far enough to expose the top edges of my areolas.
“Is that all I get? You’re still a tease.”
I turned, dropped the blouse, and let him watch me unclip in back.
“You better turn around,” he commanded. The straps still kept the cups over my tits. “Is that all I get?”
I leaned over and started to unbutton his shirt. Of course, his hands slid under the loose cups and palmed my boobs. I wiggled my shoulders. The bra fell across his arms.
“Oh God, Candy. Still amazing after all these years,” he complimented. “But you’re still half dressed.”
I took off his shirt, pulled off his tank top, “You’re so buff,” I remarked and gave a quick squeeze to the ridge in his pants. Then I stood up in front of him. I hooked the elastic waistband of my pajamas and pulled them down far enough to reveal most of my thong.
“Wow, that’s a new one. See-through. So hot!! But what are you hiding,” he complained. I dropped the pajamas ’til they fell over my shoes. His hand went between my legs and pushed the thong against my clit. I loved the feeling of the cool damp fabric between my lips.
“Aren’t you being a naughty boy,” I teased. I reached down, unzipped him, took his cock out, and laid it flat against his belly. Then I turned and pressed the thong against his shaft. I wondered when the last time was that he had a lap dance.
As I started to rub, he asked, “Where did you learn to do that?”
“A girl has her secrets,” I replied. I didn’t tell him about my experience as an 18-year-old stripper (with extras). My left hand pulled my thong aside, and my right hand held his shaft upright. “You’re OK with this, right?” This was the moment we’d been waiting years for. Hearing no answer, I eased myself down. “Oh yes, yes,” I exclaimed.
He replied, “Oh, yes. So hot inside you. So great. OHHHHHH. I’ve wanted this so bad.”
I rode him for several minutes, but before he could cum, I stopped. “Let’s get in bed,” I suggested. As I stood back up facing him, I stepped out of my heels and freed my feet from the PJs.
Derek pulled my thong down. I stepped out of it. I was finally nude in front of him. “You’re so beautiful. Still so beautiful.” His hand went between my legs again. Two fingers inside and his thumb on my bump kept me going ’til I started to shake.
“Come on. Come on.” I ran toward the bedroom. “You’d better be naked the next time I look at you,” I demanded. I heard the rustle of his clothes as I pulled aside the covers. I flopped on my back with my knees up and apart. I had just put my fingers on my clit when Derek rushed in, his cock flopping left and right as he moved.
Derek climbed between my legs and fell on top of me. With his dick against my belly, he began by kissing my neck and then my ears, favorite erogenous zones for me. When our lips met, our tongues played as his fingers squeezed and twirled my nipples. I sucked on his tongue ’til he pulled off. Moving down, he gently sucked all over the soft skin of my left breast. Then he moved to the right one. He moved his hand off that one and toyed with my nipple with his tongue. My whole body tingled and my belly contracted against his chest. I used to get mini orgasms from nursing. I thought how hubby Arthur would start that same reaction as he tasted mother’s milk. Derek took my other tit in his mouth as my abs contracted again and again. By the time his mouth sucked on my pussy lips, I was coming hard. When his tongue touched my clit, I started squirting.
“Fuck me. Fuck me now, Derek,” I pleaded. He climbed back up, rubbed his cock around my opening, and in one thrust, drove that cock as far in as it would go. I wrapped my legs around him. “Fuck me. Fuck me hard.” He pounded away, grunting loudly, as he squeezed my tits, not too gently, and pushed my mouth open with his kissing.
“Cum inside me. In missionary first,” I managed to say as I pushed against each stroke. “Oh yes. Facing me. Filling me. OH OH OH.” And it happened, emptying his love deep inside me, the full consummation of our long-delayed adultery. “Oh Derek! Oh Derek! Don’t stop.”
But when was done, I still wanted more. I pushed him onto his back. His cock had softened but was still enlarged. I climbed between his legs and held it up. I licked his thighs. I licked below his balls. I even licked his asshole. Then I licked and gnawed on his sex tasty shaft and tongued that sensitive area behind the head. With a finger in his butt, I wrapped my lips around his tip. Indeed, he was getting harder. I took it deep in my mouth and sucked. When he was ready, I straddled his hips and used his rock hard organ to play with my swollen labia and light my clit back up. I played with it back and forth between there and my vagina. I rubbed the wet tip on my butt rim – “Something for another time,” I murmured – and held it at my opening.
“Oh Candy, take it. Take it,” he begged. And I did. Deep inside me, riding as fast and hard as my knees would allow.
That went on for several wonderful minutes. I love to move a man’s cock from side to side, at every angle, in my excited vagina. But I had other desires. “Doggy,” was all I said. I rolled onto my knees. He licked my messy cunt. Oh, that was good. Without me begging, he sensed it was time and entered me again. He held my tits as he slammed in over and over. I was so glad it was round two. He kept on forever, but then it was time. Jet after jet of his jism filled me again.
We fell apart, exhausted. But when I did have some energy, I got up and went over to my suitcase. I dragged out a black cloth bag, held closed with the usual pull strings. I told Derek, “I should have mentioned we’re having a threesome.” He was stunned until I pulled open the bag and took out a red penis vibrator dildo. “Meet Red.” I told him how the blue penis I had used to fuck me in our online Covid work-at-home trysts had passed away from overuse a year ago. He broke out laughing. I just had a huge smile.
I switched Red on and knelt facing it. I started by licking the plastic balls, shaft, and tip. Then I took him in my mouth. It chattered annoyingly against my teeth, so I quit and adjusted my knees so I was in doggie position. Reaching under me, I played with it on my pully lips and up and down my slit. Derek was watching, of course, and shaking the bed with his own strokes. “Damn,” he exclaimed when I shoved Red into my gaping hole.
“You can help him,” I said. Derek took hold of Red and started pumping it in and out of me. I admit, it felt damn good, especially when I didn’t have to do all the work, LOL. After a few minutes and with a struggle, I extracted a bottle of KY I had secreted in the nightstand. “He likes DP,” I told Derek. “You’ll need this.”
“Holy shit,” he exclaimed.
“In my asshole and on your shaft. Red uses that hole at home, but I figure you might want that.” I felt the cold liquid dribble between my butt cheeks, and Derek’s finger pushing some in. There was a pause; took care of his part. Then his dick was at my asshole. When his tip touched me, I said, “Slow at first, OK. Then, have your fun.” He was gentle, like I asked. It’s uncomfortable for me to let something that big push me open there. But then, it’s so satisfying. Anal sometimes even gives me an orgasm. Not this time, just deep satisfying pleasure.
He was loving it, of course. “I feel it vibrating,” he gushed as he pounded my rear. “Oh shit, so amazing. Oh shit. Oh shit.” Red’s stimulation was too much for him. It only took a couple minutes for his cock to erupt in my rectum. His seed leaked out as he withdrew.
We flopped on our backs, exhausted. I pulled Red out. “Let’s take a shower and go back down for a drink,” I suggested. We washed Red off and lathered each other up, with special attention to our crotches and chests. It was clear another fuck was going to happen in there, but, “I have to pee,” I said.
“It doesn’t hurt anything to pee in the shower,” he offered. A bit embarrassed, I let go. The spray washed down both legs. Looking intrigued, he pulled me close and put his horizontal member between my legs. I closed my legs to hold it in the flood.
“That’s awesome,” he said as my stream flowed over it and even out my backside. When I was done, he said, “I have to pee, too, but I can’t when I’m hard.”
“That’s OK. I never liked the thought of water sports,” I said. Leaning back against the wall, I rolled my hips forward to offer my pussy. His shaft glided in. The shower water warmed us both. He lasted much longer this time. I turned and leaned against the wall below the shower. The warm water ran down my back as he finished fucking me.
We went to the bar ten minutes apart. Now in jeans and a sweater, I joined three other company people at a table for six. I ordered a touristy Chicago Fizz. Derek came in wearing a sweatshirt and sat next to me. He ordered a local IPA.
The others were just finishing their drinks and left us there. “You two have fun,” the only woman in their group remarked.
“If only,” Derek quipped, feigning innocence. But we did.
I stayed in his room with an alarm set to get me back to my own room before breakfast started. We romped ourselves to sleep and again when the alarm went off. That night and most of the following week’s Chicago nights.
