I’d never been with another man, and I wasn’t sure if I was being hit on, but the frank directness of this guy was somehow reassuring
He approached me in a department store. He noticed me from the other side of the store and made a beeline for me. Then he stood right in front of me and said nothing, as though his actions didn’t need explaining.
I looked at him quizzically. “Have we met?”
“We have now,” he replied confidently, extending his hand.
I hesitated, but took his hand. It was large, warm and dry. He had a frank face, slightly sunburnt, and a thatch of messy, light brown hair. He was an inch or two taller than me, with a manly figure, and he was dressed like a gardener. Not the kind of guy you expect to approach another guy.
“I’ll be outside when you’re done here,” he said simply, as though we’d reached an understanding.
I’d never been with another man, and I wasn’t sure if I was being hit on, but the frank directness of this guy was somehow reassuring, as though, whatever he had in mind, it couldn’t be that bad. When I left the store he was waiting for me, standing in the sun, leaning against an old truck. He gave me a friendly nod and opened the truck door. I wasn’t sure what was propelling me, but I didn’t sense any real danger, so I went over.
“Are we going somewhere?” I asked, playing along.
“My place,” he said matter-of-factly.
“Really?”
He nodded.
“And where’s that?”
“A mile and a half up the mountain.” He pointed.
I hesitated. Was I really going to do this? Then, without knowing why, I climbed into the truck and wondered what had come over me. I couldn’t understand where this impulse came from. It wasn’t even an impulse, really, or a decision. I was just going along for the ride – literally – because he had made it easy. In fact, he had made the decision for me. I took a deep breath and tried to relax.
“You do this often?” I asked a bit anxiously, as he shifted through his truck’s gears.
“Sometimes, when it seems like the right thing.”
“How do you know?”
“Instinct.”
I smiled at that. His answers were uncomplicated but not unthinking, and he gave them with a readiness that suggested a settled mind.
He lived on the side of the mountain, in a house with huge windows overlooking the city. I could see that the view would be spectacular when night fell and the lights came on. In the same room, on the opposite wall from the windows, there was a striking painting of a naked woman, all fleshy curves and splashes of color.
“Wow,” I said, nodding at it. “Are you a painter?”
He chuckled. “No, I’m a landscaper. My wife did that.”
I was surprised and, I couldn’t deny, relieved. “Your wife! Is she around? Will she be… joining us?”
“She’s out of town, but you can meet her another time if you like.”
Wow, I thought. Nothing fazes this guy. I wondered what kind of relationship he had with his wife, and what scene they were part of. He saw me turning this over in my mind but he breezily ignored it.
“Drink?” he asked.
“Yes. Thanks.” I was nervous and felt like I needed one.
“What’s your poison?”
“Dry martini, if you can manage it.”
He raised his eyebrows. “A serious drink.” To my relief, he didn’t ask whether I wanted it shaken or stirred.
The bar ran along the wide windows of the living room, so I sat on one of the stools and looked out. The view was magnificent. “Great place you’ve got here.”
“Thanks. We’ve been working on it for years and it’s nearly finished. Olive?”
“Yes, thanks.”
He brought our drinks over and sat next to me at the bar.
“So, this is your first time?”
I began to panic and feel defensive. “First time for what?”
He looked at me silently, his eyes telling me we weren’t going to play that game.
I gulped. “OK, yeah. I’ve never even thought about it really.”
“You normally see girls?”
“Yeah, and I used to be popular with them, but then…”
“What happened?”
“I don’t know for sure. I had a few bad breakups, I started getting rejected… I guess I lost my confidence. These days, I don’t even know what to say to them, and the harder I try, the worse it is. The moment they sense I’m into them they start avoiding me. In fact, they can’t get away fast enough.”
“I’m sure it’s not that bad.”
“Oh, it’s bad. I’ve had some humiliating moments. It’s like they can smell my fear.”
“Women hate uncertainty,” he pronounced knowingly. “Time for you to try something, or someone, different?”
It was obvious he didn’t suffer from uncertainty. In fact, that’s how he’d got me into his house, drinking a martini within half an hour of meeting me. He didn’t leave room for doubt. I understood the appeal of that, but it didn’t mean I wanted him in my ass. “I’m really not sure I’m ready for… something different,” I told him.
“I’ll tell you how it was for me,” he offered.
“OK…”
“My wife came home one night with a guy – a boy, really – friendly and good looking. The two of them got along great – made each other laugh. At first I was angry. I couldn’t understand what she was up to. I wondered if she thought she could open up our marriage without even asking me. I was ready to drag her aside and give her a piece of my mind, but then I noticed signs that the boy was gay. After a while, I decided my marriage wasn’t in danger, and I started to relax and enjoy his company. He really was a smart, funny kid. We had a great dinner with good wine, and we all got pretty drunk. The kid got too sloshed to drive home, so we invited him to stay the night. And that’s how it started.”
“A nice story,” I said. “But I’m not gay, and your wife’s not here to break the ice, or be the meat in the sandwich, or whatever she did to get you and that kid into bed together.”
He chuckled. “The point is, I wasn’t gay either.” He hopped off his stool. “Another drink?”
A martini is a very strong drink, and the one I had was doing its work. I was starting to feel loose and a bit reckless. “Sure,” I said. “But I think I need a bathroom first.”
“The one down here’s being fixed. You can use the ensuite upstairs. Turn right at the top.”
By the time I reached the top of the stairs, I was doubting the wisdom of saying yes to a second drink. I felt a bit woozy and lightheaded as I stumbled into the bedroom and ensuite. While I was in there I asked myself what the hell I was doing, but when I left, I still didn’t have an answer.
On my way back through the bedroom I noticed a wardrobe half open. I could see a lacy black dress, and next to it, a red one. I went over and opened the door. Suddenly, I had a new understanding of the power this guy’s wife had over him. The wardrobe was filled with the sexiest clothes a woman could wear. Strappy, stringy, backless dresses, miniskirts, sheer blouses, trimmings in lace and fur, a few pieces of velvet and leather, and lots of skimpy summer sundresses. There was even a vintage crochet bikini.
Those clothes had one clear message, and as I looked at them, a strange feeling crept over me. I found myself imagining how a woman would feel when she wore them. Obviously, if you dressed like that, you didn’t need to do anything else to attract a man. He would do all the work – come up with the pickup lines, flash money around, and desperately try to make an impression. You could be friendly, playful, flirtatious, and just watch while he tried his hardest to persuade you to take those clothes off. And then it happened. I felt a stirring in my crotch as I imagined, well, being a woman.
A male voice came from the doorway behind me. “Her underwear’s in the top drawer over there, if you’re interested.”
I turned and scrambled to say something. “I was just…”
“I’ll leave your drink here,” he said, cutting me off as he placed the martini on the chest of drawers. “Have fun.” Then he turned and went back downstairs.
I gulped a mouthful of martini and then realized what he’d said: have fun. That was it. Girls just wanted to have fun. The song suddenly made more sense to me. The freedom, the irresponsibility, of being the one who’s desired and pursued. No pressure, just fun. Let the men take all the risks. I opened the top drawer. It was full of silk and satin and lace in a multitude of colors. My eyes were drawn to a pair of skimpy black panties. My cock began to harden as I realized what I was going to do. Trembling, I took off my jeans and trunks, then slipped the panties over my feet and up my legs. My cock was rock hard by the time they reached it.
The panties were tiny – a very tight fit. They felt exciting but they barely cupped my balls. There was a full-length mirror on the other side of the room but I didn’t even look before I decided to try something else. I rummaged and found the perfect thing: a pair of red satin panties with black trim and, best of all, crotchless. The black panties came off, the red ones went on, and soon my balls were hanging free and my cock was standing proudly pointing from the shiny red fabric.
Ten minutes later I went downstairs in the red panties, some black stockings and suspenders, a silk camisole and a translucent chiffon robe. His wife’s shoes were all too small for me, so I finished the ensemble with a pair of her heeled slippers that I managed to squeeze into.
He was relaxing on the couch and he smiled when he saw me. “Very nice!”
For the first time I felt the pleasure of being seductively dressed. It was exciting, but I sat on the couch, crossed my legs, and covered my swollen cock with the robe. “I suppose now you think you can get me drunk and have your way with me,” I said petulantly.
“Seems to be working so far.”
“Yeah, well, don’t make any assumptions. I just thought it would be interesting to experience things from the other side.”
“Your cock seems to think it’s more than interesting.”
“That’s just the mar… Oh shit. I left my drink upstairs.”
I got up to fetch my martini. As I walked across the room in my heels and went up the stairs, I could feel his eyes on me. My cock got a bit harder. The song was right. This was fun! But as I entered the bedroom, I heard him coming up the stairs behind me. Instinctively, I jumped into the ensuite and locked the door.
“I told you not to make any assumptions!” I yelled.
He responded calmly. “I’m not assuming anything, but you seem to enjoy it up here, so I thought I’d join you.”
Seem to enjoy it? What did he mean? Did he want me to try on more of his wife’s clothes? Was that his thing? I imagined him sitting on the bed stroking his cock while I paraded around in front of him. At least then I wouldn’t have to do anything else.
“I’m not sure what you mean, but I’m comfortable in here for now,” I said, unable to think of another response.
“That’s fine,” he said. “Take your time.”
I heard him slump onto the bed and put on the TV. Soon he was laughing at some comedy.
I sat on the edge of the bath and looked at myself in the mirror. The clothes looked nice but my face was… not too manly, exactly, but boyish. I reached for a drawer and found what I was looking for. I’d never worn makeup, but I’d seen my sisters and girlfriends put it on. I chose a red lipstick, and as I applied the bright color to my lips, I felt a sensual buzz that confirmed for me what it meant to be desirable. I was making myself into a sex object, and it felt good. The feeling spread through my body. I’d never been attracted to men, but feeling this way, it didn’t matter. This wasn’t about them. It was about me. I was the attractive one. I had to control an excited tremble in my hand as I looked for some mascara and carefully applied it. I almost wished there was a wig to complete the look, but my hair was growing out at the time, so I settled for brushing it. Again, I got that feeling – the sensual pleasure of making yourself desirably female. If I was a woman, I thought, I would be getting wet now.
Finally, I felt ready to face my seducer. He was laughing even louder now, and I suddenly resented it. Here I was, hiding and trembling in the bathroom, undergoing a physical transformation, and there he was, unaware, laughing at some stupid TV show. I stepped out of the ensuite.
“What’s so entertaining?” I asked, my resentment showing.
He was sitting on the bed, leaning back on some pillows. He looked at me appreciatively. “You look nice. Come here.” He propped himself up a little and spread his legs, making room for me between them. My breath caught in my throat. Was I really going to take this step? He laughed again at the show. Oh, for God’s sake, I thought, and, partly to make him focus on something else, I climbed onto the bed and sat between his legs, facing the TV.
He was watching an episode of South Park where President Trump and Satan are gay lovers. OK, I thought, that’s a funny one. “I can’t see,” he said quietly, and he reached out and gently pulled me back against his chest. It felt strange to be held that way by a man, but I tried to relax and enjoy the show. Then I felt his cock swelling against my back, and I found myself hoping it was me and not Satan or President Trump who was turning him on.
An ad break started, and he muted the TV. My heart pounded as he slowly reached around and brushed his fingertips along the length of my cock. I took a sharp breath, closed my eyes and leaned back against him. I could feel his own cock getting harder behind me. His hand closed around my erection and he started to stroke me up and down, lubricating me with my precum. At first I trembled and tried not to move, but after a while I couldn’t help myself and I started to push my cock into his fist. With each motion, I thrust harder and pressed back more against his cock, but the rhythm didn’t last very long. The pleasure built rapidly until an ecstatic feeling overtook me and I knew I was about to shoot my load. “I’m gonna come,” I said breathlessly. He clenched his hand on my throbbing cock as my cum spurted into the air and came down in splashes on my camisole and suspender belt.
I lay back for a few minutes in a post-climax stupor. He gave me a kiss on the neck, as if to thank me, or congratulate me. I didn’t want him kissing me, but I was too drowsy to complain. Eventually, I sort of woke up and tried to face what I’d done.
“I suppose now you want me to return the favor,” I said like a spoiled child.
“Oh, I want much more than that, but let’s get comfortable first.”
Without waiting for me to respond, he eased me forward, then climbed off the bed and started to undress. “You might want to get those wet things off,” he said.
The cum had soaked straight through the flimsy clothes and was getting clammy. I sat on the edge of the bed and obediently removed the chiffon robe, peeled off the camisole, and unhooked the garter belt.
“This doesn’t mean…” I started to say, when suddenly he was standing in front of me, stark naked, with his cock pointing straight at me. He was standing the same way as he had in the department store, as though nothing needed to be said. I couldn’t deny, his cock was impressive. Not too long, but thick and veiny. He stepped forward. I knew what he wanted and, I had to admit, I was tempted. I’d never had a girlfriend give a blowjob like a porn star, and I was excited by the idea. He stepped a bit closer. Nervously, I reached out a hand, took hold of his shaft, and steered his knob towards my lips. From the moment it entered my mouth, my own cock began to harden again. He groaned and pushed deeper till his cock filled my whole mouth. Then he closed his hands around my head, spread his fingers, and began to thrust. My head became an object he was using for his pleasure, and I loved the feeling of it. My own cock was now rock hard again. When his knob hit the back of my throat my gag reflex kicked in. I tried to control it. I managed to get him down there a couple of times, but not without choking and spluttering.
“I’m sorry,” I said.
“It takes practice,” he reassured me. “Lie back.”
Somehow, I felt no will to resist. I lay back, flat on the bed, looking up at him. “What are you going to do?”
“Don’t worry. You’ll like it.”
He removed my loose garter belt, rolled my stockings off, then pulled the crotchless panties up over my cock and down my legs. I discovered that having women’s underwear removed was just as thrilling as putting it on. But what happened next shocked me. He lowered his whole body onto mine and lay right on top of me. I wasn’t prepared for this, and I began to panic as I felt his weight on me. It hadn’t occurred to me that we would do anything face-to-face, let alone chest-to-chest. But then I felt his cock sliding alongside mine, and I realized what this was for. Our two cocks rubbing against each other felt great. His was still lubricated from my blowjob, and when the saliva mixed with our precum, everything became very slippery. Soon I was loving it, and I couldn’t believe that this idea had never occurred to me. We squirmed and thrust at each other till we were breathless.
Then he did something I was expecting. Reaching under me, he spread my butt cheeks and slipped a finger halfway into my asshole. A few of my girlfriends had played with my ass, so I was ready for this. I’d even learned to like it. He immediately sensed I was OK with it and slipped a second finger in. That stretched me a bit, but my squirming loosened things up, and before long he had two fingers pushed as far up as they would go. He caressed me rhythmically, and the pleasure built in my cock and ass. Then, as I was trying to relax and not get too excited, a new feeling took hold of me. Lying there with his weight on me, I started to feel small and helpless. As I surrendered to that feeling I felt I understood what it meant to really give yourself to a man. He was taking possession of me, and I tingled and trembled in all my senses as I allowed him that privilege. Then the pleasure became too intense, and I couldn’t resist anymore. I started coming hard. My ass clenched as my cock squirted hot cum between our bodies. The more we moved, the more I spasmed. It seemed to go on for ages. When it stopped, I lay still, but he was still moving, pressing himself against me with a steady, controlled intensity.
“You didn’t come?”
“No, I’m saving it.”
“What fo…?” I started to ask but then realized. “Oh.”
He didn’t say another word. He just took hold of my naked body and turned me over.
“Give me a minute,” I begged.
“Sure,” he said. But he didn’t wait long to start the foreplay. He moved down and slid his tongue between my butt cheeks. He licked the full length of my butt crack a few times, then swirled around the rim of my ass, and before long, his stiffened tongue was darting in and out of my hole. The next thing I felt was the shaft of his cock as he rubbed it between my butt cheeks. He was getting closer, preparing me slowly for what was next, and I had to admit, it felt good. But I trembled at the thought of his fat cock penetrating me. I was terrified of the damage he could do to my virgin ass. “Be gentle,” I begged. “Of course,” he said, but then it was too late, and I gasped as I felt his big knob stretching me open and pushing inside. It was almost painful. Then he went deeper, and suddenly it really hurt. “Stop!” I shrieked. “I can’t take it!”
He lay still for a few moments, then quietly told me to relax. “Don’t worry. It’s always like that the first time. Just wait.” Slowly he began to move again, gently nudging and probing his way into me. I felt myself loosening to take him as he gradually went deeper. God, he was huge! He still wasn’t all the way in when the pain began to turn to pleasure. Something in there felt good, and my cock began to harden again. He started to thrust, slowly at first, then faster, and soon I felt his balls slapping me from behind and his pubic bone hitting my butt cheeks. He was all the way in! And then the pain and pleasure became one feeling. I relaxed into it and started raising my ass to meet his thrusts. He moved his hands under me and put one palm on each side of my stiffened cock. That was the way I’d masturbated as a kid, and I loved the feeling of it. His thrusting got harder and faster. The pleasure in my ass was building and becoming intense. We were both panting aloud as I felt my body starting to convulse. He groaned as he gave a series of massive thrusts and violently pumped his cum into me. My ass clenched repeatedly as my own cum shot through his hands onto the mattress under me.
Later, when I’d cleaned up and sobered up, he drove me back to my car in the department store car park, chatting in his friendly, matter-of-fact way. He invited me to drop by sometime and meet his wife.
“That’d be nice,” I said, without making a commitment.
When I got home I felt sore but happy, and somehow relaxed. I slept soundly that night.
A couple of days later, I was walking down the street near my house when I saw a gorgeous brunette coming towards me on the sidewalk. She had thick wavy hair, full lips and big brown eyes. Her faded jeans were a snug fit and her button-up top stretched deliciously over her plump breasts.
“Wow, you look great,” I said, without even thinking.
She looked me up and down as she went by. “You’re not so bad yourself.”
I chuckled and continued on my way.
“Hey!” She yelled from behind me. “Wanna go to a party tonight?”
I paused and turned. “Sure.”
“1180 Westgarth.” She smiled. “See you there.”
I went to the party. She was there. We made out, then we went back to her place and fucked all night. She said it was the best sex she’d ever had. No one had ever understood her so well. When I went to meet the wife of my seducer, I took her with me. But that's another story.