Older Guys are Fun

I was 24 and living on my own in a different town from where I grew up. It was far enough away that I could be anyone I wanted to be and so I got deeper into dressing up. I had a good job now, so I could afford some nicer clothes, and now that I had my own place, I could order things through the mail without worrying about prying roommates or parents.

In the city where I lived, "curious" men placed personal ads asking for guys to meet them in a coffee shop, park, or something. It wasn't to meet for sex in public, it was just to meet, sort of a way to determine if someone was gay before you make your move I guess. One day I followed up on an ad asking to meet in the back corner of a bookstore. The ad said to pick out a specific book (I don't remember the book) and thumb through it so the guy would know you were there answering the ad. It sounded interesting, so I went to the book store, in guy clothes of course, found the book and sat down on a nearby chair. After a few people cleared out of the section, an older guy sat down in the chair next to me - and by older I mean around 55. He asked if I had ever read that book before and I said no but a friend I was meeting here had recommended it. He took the hint and introduced himself and we made small talk for a bit, then he asked if I would be interested in continuing our conversation over lunch. I went along with it for now, not quite sure where this was going, but we DID actually have lunch and we got to know each other with some pretty interesting conversation. We will call him Jones for this story. Jones was basically just a bit lonely and bi-curious and also seemed to be into the fact that I dressed. We met up again a few more times in public for lunch and conversation and eventually I gave Jones the address to my apartment.

After a few missed connections, Jones found his way to my apartment one night and I could tell he was excited and had finally built up his nerve. I let him in and excused myself to my bedroom to get dressed. At this point I was basically keeping myself smooth from the neck down on a full time basis, so all I needed to do was apply my makeup, shake out my wig, and get a dress on. I douched quickly before starting my makeup. The makeup was (and is still) the hardest part of my routine, so I didn't present very well that night. For my outfit, I chose light pink panties with lace strappy sides and a matching bra. I had pads safety pinned inside the bra cups to fill out my top. I squirted a bit of lubricant deep into my ass using a syringe applicator I kept around just in case. I chose a form fitting black cocktail dress with a white collar, what I called my Audrey Hepburn dress, and a pair of black 5 inch heels. My legs were freshly shaven just before Jones showed up, so I skipped the stockings and went with bare legs. At the time my go to wig was a straight, auburn color with bangs that swept to one side (very 90s) and length down to the center of my back.

I walked into the living room and found Jones sitting on the couch. As soon as he saw me his eyes narrowed and a sly smile crossed his face. I'd never been on the receiving end of a look like that from a man; but I liked it. I turned off the living room light, leaving only the glow from the hallway light and television. I figured the low light would help cover my half-assed makeup situation. I sat down on the couch next to Jones and we talked a bit. He complemented my hair and my dress as I did my best to keep a feminine voice through the conversation. I wasn't perfect by any means; but I could tell Jones was down to play pretend with me anyway.

Jones leaned in to kiss me and I guess because of the age difference or something, I was startled a bit; but let it happen. He moved to my neck and then my ear lobes, when one of my clip on earrings popped off and fell in between the couch cushion. He didn't stop when the earring fell and I could feel his hand rest on my knee, then slowly slide up the top of my thigh.

Just as his hand almost reached the cock in my panties, he swerved over to my hip and slowly crept up inside my dress until his hand rested partly on my stomach with his fingers around my waist. He kissed me deeper and at this point I realized I very much liked the feel of a mans hands on my body. I started to get hard, so I pressed my thighs together to keep my cock from popping loose from where it was tucked into my panties.

Jones stood up in front of me and I could tell through his dress slacks that he was hard. Jones unzipped his slacks and reached down to hold both of my hands in his. He moved my right hand into his unzipped pants, so I reached in, pulled his underwear below his cock, and pulled it out of his pants. His cock was average to short in length but he was pretty thick and he wasn't even fully hard yet. I was slightly afraid he was about to put this thick thing in my mouth; but instead he guided my hand over his shaft and started to move it up and down. Through later dates with Jones, I found that he has a fetish for handjobs from girls with large hands - so I was right up his alley. Honestly I'm not experienced with blowjobs anyway; but this I know!

My right hand slowly slid up and down his shaft, squeezing slightly at the base each time and turning as I worked toward the head. Every third stroke or so, I cupped my palm over the head of his cock and turned it slightly before going back down the shaft. With my left hand, I worked his pants and underwear down a bit so I could wrap my left hand around his balls. I cupped and lightly squeezed his balls each time I worked my other hand up to the head of his cock. I could feel his balls draw in a bit and knew he was getting very close to cumming.

I stood up and took Jones's hand and led him down the hall to my bedroom. We left his pants and underwear in the living room and he pulled off his shirt as we walked. When we got to my room I was so hard at this point that I immediately sat down on the edge of the bed, rather than stand there pitching a tent in my little black dress. I reached over to the night stand for a condom and rolled it over Jones's hard cock and then placed a strip of lubricant along the shaft and stroked his cock with in hands. He let out a deep breath and I thought he would come right there, so I backed off. Jones leaned toward me and laid me back onto the bed. His hands ran up the outside of my legs and pulled my dress up into a bunch just above my belly button. Jones grabbed the back of my panties and pulled them slightly down my thighs as I raised my knees as high as I could toward my chest. I could feel the lace band of my panties stretch tight and dig into my thighs as I wrapped my legs around Jones's back. Jones leaned toward me and gave me a very light kiss as I felt his cock push into my ass. Jones was about as thick as my largest dildo, so I could feel the slight sting and stretching of my asshole as he entered. He pushed hard against me to go in as deep as he could and then, feeling the tightness I guess, he pulled all the way back out. His next thrust was a bit slower, as if he was trying to be more gentle, but his cock had already dipped into the lube I had put in my ass earlier, so there was almost no resistance this time. I could still feel the stretch, but no sting this time, and the fullness was exciting to say the least.

Jones laid on top of me with his head in my hair, breathing deep into my neck, and pushed in and out of me in a steady rhythm. The entire time his hands slid smoothly from my thighs to my butt and to my waist. Each time his hands moved to a new part of my body he would squeeze slightly and slide them to the next, I was in heaven! At one point my cock jumped a bit like I might cum and I instinctively tightened by sphincter around Jones's cock as a reflex. Jones bucked slightly and let out a short groan and pushed his hips hard against my ass. I could feel his cock swell slightly inside of me and I was pretty certain he had come.

Jones slipped out of me and laid across the bed. I laid there with my dress pulled up and my panties at my knees as he traced my legs with his fingers. Jones took off one of my high heels and slowly massaged the arch of my foot and my toes. I had painted them bright red a few days earlier so they were still very pretty. We talked and laughed just like we had done weeks before during our lunches. Jones finally had to go, so I followed him to the front door as he collected his clothes and got dressed. I had gotten my dress and panties back into position and still had my heels on. At the door he wrapped his whole arm around my waist and pulled me in close to give me a deep kiss. It was sort of an awkward, old guy kiss, like from an old movie, but it still felt very nice.