Man’s Soft Caress

It was exhilarating, people pushing against me from all sides as our bodies moved to the music. I used my ass to clear a little space and Terry pushed in closer, appropriately fending off aggressive male dancers whenever they approached. He was actually a good dancer too, not that you could tell much as we were all so cramped together, but there was confidence and familiarity in the way he moved his hips.

“Ray… it’s good to see you smile,” Terry yelled over the thunderous music.

Terry was one of the few people at work that I allowed to call me anything but my full given name, Raylin; and he was also one of the few men at work that wasn’t an egomaniac. That’s the world of consulting — male-dominated and full of very competitive people who think they are the smartest person in the room.

Terry and I had been co-workers at Bradford Consulting for the past two years. Tonight we were celebrating the conclusion of our latest assignment, an intense engagement with an advertising firm in Chicago. For weeks we had flown in and out of Chicago and spent long hours and sleepless nights preparing our final client presentation. Today, we presented to the board and it went well — very well.

To celebrate, the whole team met for a fancy dinner and then drinks at a cocktail bar. I would rather have been out celebrating with my real friends as opposed to co-workers but we had worked hard together, succeeded, and now I just wanted to celebrate and feel that all the sacrifice was worth it.

After dinner and one seemingly obligatory drink at the cocktail bar, Ajit and Rob excused themselves first, claiming early flights in the morning. Sarah left soon after with a story about meeting up with some local friends from college. That left me and Terry sitting at the bar with glasses empty, debating whether it was time to call it a night.

“When did celebrations start ending at 10 pm?” I asked.

Terry shrugged a bit, “I hear you but I think dinner and a drink was ‘Going Big’ for Ajit and Rob, they have kids and all that… and you know Sarah, I’m pretty sure her last drink was a Shirley Temple and I’m not buying the college friend meet up. She’ll be cozy asleep in the hotel in five minutes.”

I laughed and looked down into my empty glass before responding, “Ok then, it’s up to us, I guess. Go big or go home. Right?”

Terry winked, “I’m not sure how big you and I can go, but I’ll be your wingman.”

I sat for a minute and imagined Terry and I sitting and chatting over cocktails for the rest of the night. I liked Terry well enough but that sounded terrible. I didn’t want to sit around and talk all night. I wanted to let loose.

“When’s the last time you really danced?” I asked with what I hoped was a devilishly enticing smile.

On the dance floor, packed like a sardine, I somehow felt free for the first time in forever. With the pounding music and flashing lights, there was no room for intellectual conversation or the politics of business. There was none of the bullshit from the male-dominated consulting world I was so ready to leave behind. And surprisingly, I was having a lot more fun with Terry than I had expected.

Terry wasn’t my type in the least. I liked my men strong. I liked big hands and five o’clock shadows. I liked my men to take me with respect but, nonetheless, I liked them to take me. I liked my wrists pinned back against the bed and my breath taken away with thick deep thrusts. I liked my ass slapped and my hair pulled while I arched back and braced myself on all fours. I liked the way a strong man would flip me on to my back, spread my legs without request, and stare down at me like an animal as he rubbed his cock against my clit.

Terry was none of these things, in my mind. He was slight. He was polite. He was the team’s best numbers guy. He was the one that made sure our grand recommendations would actually pencil out in reality. He didn’t have the typical Consulting personality. He didn’t care about taking credit. Terry was a true team player.

And being a team player was exactly what he was doing tonight. He could see how much I wanted to go dancing so he came along without complaint. He could tell that I didn’t want the men dancing around me to cut in and make a move, so he stepped up to protect me. And now he could tell that I wanted to be a bit flirtatious and he willingly leaned into my invitation.

I had yet to tell him that I was leaving the firm, but that knowledge and all of the alcohol let me see Terry in a different light. He wasn’t my type but he wasn’t unattractive either, and it was in this moment that I began to appreciate the same delicate features that had always placed him clearly in the coworker/friend category.

Each time Terry moved in closer to defend my body from another man’s overly aggressive thrusting pelvis, he seemed to linger a bit longer; or maybe it was me, holding him with less inhibition. I distinctly remember the first time he danced closer and I put my arms around his neck for just a few seconds — how my body warned me that I was clearly blurring work boundaries. But I didn’t think of Terry in a sexual way, which made the flirtation feel harmless.

I remember my hands moving down from his shoulders, down the arms of his long-sleeved button-up shirt to touch his hands for the first time. That moment was brief and felt taboo but soon, as we danced, our touching felt normal and appropriate enough for an after-hours celebration between friends.

As the music slowed, I moved forward and rested my head on his chest and shoulder. We were similar in height, but he was still slightly taller. He wasn’t a small man but he was slender and thin. I suddenly felt a bit too close so I pulled back and let my hands drop down to take his. His hands were jarringly soft like the hands of a delicate woman. I closed my eyes for a moment and felt the microscopic motions his thumbs made on the back of my hands.

For the first time, Terry had me thinking dirty thoughts. They were odd thoughts for me, filled more with the soft sensual touch of another woman than the hard pounding rough sex that I usually craved from my men. I felt no real attraction to Terry in a visual sense, and no aversion either. But now, as I closed my eyes and felt his soft touch, my imagination took me to a slow, sensual place where I yearned for subtle tenderness.

Back at the hotel, it was easy enough to convince Terry to come to my room for a nightcap. We were both getting a little tired but he was still willing to entertain my desire to celebrate.

I grabbed a couple of beers from the drinks fridge and popped them open before handing one to Terry. We didn’t need more alcohol at this point, but it was my excuse for inviting him up in the first place.

I suddenly felt that I had to tell Terry I was leaving the firm. “Terry, please don’t tell anyone but I’ve accepted a new job with another company. I’ll be announcing my resignation next week,” I said.

Terry smiled, “I figured as much. You wouldn’t have invited me up here or even to go out dancing if you weren’t leaving soon.”

“What do you mean?” I replied quickly.

Terry paused, “It’s just that it’s so hard to compete as a woman in this firm. You don’t need a bunch of guys talking about your late-night exploits. It’s silly but it’s still how it is for women in a lot of companies.”

I took a deep breath and nodded my head before responding, “Being a woman in this firm sucks, to be honest.”

Terry nodded too as he confirmed my feelings, “I know.”

The room was quiet for a moment before I spoke again, “Wanna fuck?”

For anyone else, this would seem off-puttingly blunt, but our company culture had taught us both the value of clear, no-bullshit, aggressive communication. It also gave Terry an easy out as he could always respond with a joke and let me save face. Plus, it was getting late and I was leaving the firm so, fuck it.

Terry’s face was serious, “Just to be extra clear, are you asking if I want to fuck you or are you inviting me to fuck you? Two very different things.”

“The latter,” I responded with a smile.

Terry stood and took one step forward as he unbuttoned his shirt and continued our dialogue, “Just to make sure we’re on the same page, you’re leaving, so you’re not worried about your reputation at the firm, and you see me as ‘safe, casual, fun.’ Right?”

I stood too and looked him in the eyes as I spoke, “Not exactly my words but true enough. I don’t know if I’m your type or if you’re mine, but you’re definitely the only co-worker I would consider fucking and I really appreciated you coming out tonight.” I turned my back, leaned my neck forward, and pulled my hair to the side, “Zipper please.”

“I know I’m not your type,” Terry said, as he took the zipper between his fingers and pulled, the back of his delicate hand sliding down my spine to meet the top of my panties.

I turned back toward him as I let my dress fall and began to unclasp my bra.

Terry tossed his shirt to one side and kicked both shoes off. He undid his belt, unbuttoned and unzipped his slacks, and let them drop to the floor as well. He reached down and removed both socks and before my bra hit the ground, he removed his boxer briefs as well.

I stopped for a moment and stared at the man in front of me. He was most definitely not my type. He was skinny. His chest was hairless. Stereotypically, he was feminine in more ways than he was masculine, except for having a cock of course. But even that seemed to be diminutive. To be fair, his penis was still soft, so I couldn’t make a judgment on size, but he didn’t seem to care.

I dropped my panties and turned the lights off. It was dark. I thought it was better that way. Terry stood still as I stepped forward and reached my arms up and around his neck as I had earlier on the dance floor. Our chests pushed together, our stomachs met, and his soft cock nuzzled against my pubic bone. I felt his slender shoulders and arms, then his sides, and as I rested my head on his shoulder, I felt my hands rest on his small tight ass.

Then I felt the hidden sensuality of his hands as he moved them softly, up and down my back. We stood as he tenderly massaged my shoulders before working his way slowly down each vertebrae. From the base of my spine, he pushed his hands more deeply into the muscles running down and around my ass. I breathed deeply and let my head sink more deeply into his chest as I let out an audible sigh.

His touch took away whatever apprehension I had and it also sent me into a state in which I stopped thinking about what this sexual experience was and what it wasn’t. I stopped thinking about who I was with and leaned into the touch of the moment. I leaned into the softness, the caring, the sensual hands.

Terry took control in his own way. He directed me to the bed, laying my head back against the pillows. He caressed each thigh as he slowly parted them, letting his thumbs glide from my knees down to my stretching groin. He lowered himself on top of me and kissed me for the first time. I felt the tender taste of his delicate lips pushing against mine. At first, it was only lips, but his tongue seemed to feel my growing excitement and it began to perfectly intertwine with mine. I felt the shaft of his cock against my pussy, not pushing, not begging, just patiently rubbing against my clit as it began to grow.

He moved down to kiss my shoulder and take my nipple into his mouth. His tongue swirled softly over my breasts and a rush of wetness came to my pussy as I began to want to feel him inside of me. As he moved to my breasts, his cock slid down from my clit, parting my lips and settling, the head against my entrance.

I whispered, “I want to feel you. Do you have a — ?”

Terry interrupted as he lifted his head from my breast and began to kiss his way down my body, “You will.”

He positioned his head between my thighs and began to work his tongue up and down my lips. He took his time to stimulate every part of my pussy but he didn’t linger too long, somehow knowing exactly when to change location or rhythm or technique. I don’t know if it was intuition, my breath, my sounds, or even my pussy giving him little twitching clues, but I felt like only a woman should be able to make a pussy feel like this.

Finally, his tongue ran over and around my clitoris and his mouth began to suck it softly. I tried to breathe deeply and keep my orgasm at bay but he had built my arousal so perfectly and his soft sucking and swirling of his tongue on my engorged clit was just too much. I was quiet and a little embarrassed as I came in moments without his fingers or cock ever pushing into me. I think he knew, but we never talked about it.

“Turn over and lay on your front,” Terry said with tender authority.

After cumming I thought that the rest of the experience was more for him than me. I imagined he wanted to show me his manliness and do his best to pound me from behind. I loved his soft touch and I remember feeling disappointed in that moment that he was going to end this by trying to compete with the brawny big cocks that had pounded me in the past. Still, he had made me cum and it was the least I could do to give him the fantasy he was looking for.

He stood and grabbed something from his pants, and then stepped momentarily into the bathroom. I waited, flat on my front as requested, my legs open, waiting for him to enter. I felt confusion on his return as he moved my legs back together and straddled me, my ass just below him. I heard the squirt of the lotion bottle he must have grabbed in the bathroom and his hands began to, once again, remove the tension of the day and even the tension of my orgasm moments before. I relaxed fully as he rubbed my neck and shoulders, back and sides, and ass.

He massaged me for long enough that I began to fall in and out of incoherent dreams — dreams about invisible touch, energies running around my body and making me cum at their whim.

I felt his hands leave me for a moment and heard the rip of what I half-knew was a condom wrapper. There was a pause and I felt him lower down for the first time so that his cock rested between my ass cheeks. I was awake again and for the next couple of minutes, I felt my pussy begin to beg for his cock as he continued the massage as if he had no urgency at all.

Finally, as he worked his hands down my back, I could feel one hand leave my body to grab his cock and guide it back to my entrance. His head dipped into me without effort as both hands returned to my back. He massaged up to my shoulders, then pulled back on the muscles connecting my shoulders and neck, the leverage pushing him deeper inside.

He must have grown immensely — or it was the position, or the fact that he hadn’t tried to fuck me or finger me the entire night — but his penis felt huge. It was hard to tell because I had only seen him soft and he was taking such good care of me that I hadn’t even reached down to feel his cock, not even once. I imagined now that it was thicker rather than longer, but every time I thought he was in all the way, he would push a little deeper.

As he moved slowly, I tucked my hand under my pussy to rub my clit. Usually, after orgasm, it’s too sensitive to touch again, but time and the massage had reset everything. I raised my ass up into him to let him show me his true depth and felt down to where my pussy and his cock melted together. It wasn’t my imagination, he was thick and I was dripping wet.

As I rubbed my clit slowly, he moved even more slowly within me. He moved so slowly that I could feel him continuing to grow inside of me, reaching deeper, filling me, stretching me. Now I could feel every bit of his swollen cock, the ridge of his head, the contours of his veins, the thickness of his base.

My past experiences begged him to pound my pussy into the mattress, but I stayed focused on his soft and tender movements and the connection I felt with the shape of his swelling penis.

Then Terry whispered into my ear, “When you start to cum, I’ll fuck you hard, the way you like.”

His words put me over the edge for the second time. How did he know what I craved and had become so accustomed to? How did he know this pussy, this body, so well?

I rubbed harder and pushed back into him. I felt a sudden rush in my pussy, my juices surging. He pushed slowly and deeply, as deeply as I could ever want, pulling my hip bones up and sinking himself into me. I heard his breath quicken and mine along with it.

My voice grew louder with each word, “I’m gonna cum. I’m gonna cum… oh fuck me… I’m cumming.” And I began that deep steady groan only made from the deepest orgasm.

I pulled my hand up and away from my clit and braced myself, both hands outstretched in front of me. The orgasm ran through me and as it peaked, he unleashed a series of long deep thrusts that extended the orgasm and forced another series of guttural moans from somewhere deep in my lungs.

As he felt me finish, he stopped the pounding and pushed as deeply into me as possible. He held his cock perfectly still so I could feel every flex and twitch as his balls tightened against my lips, his condom filling with cum.

After his orgasm, we turned to lay on our sides in unison and I purposefully kept my ass pushed back into him so his cock would stay in place. As he spooned me, I was comforted by the heat of his slowly calming breath on my neck and the feeling of his cock still pulsing inside of me, slowly retreating.

Terry still wasn’t my type, but what I thought was purely a one-night stand now seemed like something I should definitely sample again in the future. And as I felt his tender cuddle and began to drift to sleep, I wondered what other experiences I might be missing. Could it be that “my type” might not be my type at all?