I've been single for a while. A sixty something six foot, hundred and ninety pound gay man with salt and pepper hair, a good job, and a modest paid for suburban home in a small Southern Ontario city.
I'm too old for the bar scene. The music is too loud. The pretty boys aren't interested in an old fart, and I'm not interested in an unshaven, pot belly leather biker type. So I decided to try a gay online dating site.
###
Kevin started calling me 'Debbie' and it stuck, although my real name is Darrin. I'm five foot four, hundred and thirty five pounds, and have shoulder length auburn hair (this month). I've a fun job in a beauty salon, and rent a cute two bedroom apartment above it from my boss lady.
I kicked Kevin out when I realized the bitch was stealing from me. The Toronto 'gayborhood' is, like, an hour or more drive away, so like, nothing closer. So I thought 'what the fuck Debbie?' and started looking at dating sites on the 'net.
***
Oh my! There's a pretty little faggot. He'd be fun to play with. Says Ontario. Type in his code number. "Hello Darrin. My name is John. Would you like to talk?"
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Ooh, nice suit. An older gentleman. Never had a relationship with an older man. Older woman, but that was like, ages ago. Marlene was cruel. He looks kind.
"Hello John. I'd like to chat. Can we hook up here tomorrow the eight? Would you like to see more intimate pictures of me?"
###
Well,fuck me gently. A come on to sell his cock shots. I am so naive. Probably all the stuff on these sights are trying to sell something. Well, even on line I can't be rude, and it's eight o'clock. "Darrin, I'm not interested in buying gay photo art. Best of luck and good health. John."
There's a quick reply. Good customer service anyway. Ha.
###
"Oh, John, Sir, I've offended you. I've never online dated before, I didn't know the protocol. I'm not selling anything, I just want to meet someone. Sorry."
Well, after my fuckup, we chatted. John liked when I called him 'Sir'. I told him I was 'Debbie' and we started meeting online a few nights a week.
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"Debbie, I'll be straight with you. I'm not looking for a long term relationship. As I said, I was married to a lady for a while, and she's still my friend, but I'm no good at long term commitments. What I hope to find is a nice young man who wants to play with me for a while. Go on dates, have some fun, no strings."
###
Oh well, faggots can't be choosers. "I understand, and appreciate your candor, Sir. I'd like to meet you in person. Maybe we could have some fun together."
Turns out Sir lives in a city on the 401 corridor too. He suggested I choose a restaurant where we could meet for our first date. A public place. "not a burger joint, or a Timmys (Coffee chain) Debbie, someplace sort of mid range." Oh yes!
###
Debbie chose a restaurant just off the highway in his city, about half an hour from mine. I parked beside his older Chev Cavalier.
Just as sweet in person. Low heel ankle boots, tan and brown stripped trousers, pink golf shirt under a dark brown leather bomber jacket with a grey fur collar, hair tied back in a pony tail reveling subtle gold ear studs. Gay but not 'flamer' gay.
###
Well, Sir is just as handsome in person, and a bit of a hunk! Canvas trench coat open to reveal a medium grey suit, white shirt with powder blue pin stripes and a maroon tie with diagonal dark blue, pink and mauve stripes.
"Hello Sir, I'm Debbie."
Hello Debbie. My you're just as pretty in person."
"Oh Sir!" I blushed. What a deep sexy voice.
###
"Shall we go in? Looks busy, did you make a reservation?"
"Of course sir. Just like you told me."
Sweet young thing. Is it wrong to desire a young one? Not if he's over twenty one, right? We were soon chatting comfortably over dinner. We're going to have fun together.
We walked back to our cars. I pulled the paper out of my jacket pocket. "I'd like you to come visit me next weekend. Here's instructions on how to find my place and my phone number. When you get to the corner of my street and Wellington, call me from the four way stop. Wear something pretty."
###
We shared our first kiss in the parking lot. Sir was a good kisser. His embrace was gentle, but I could tell he was strong and fit. When I got home I changed into my favorite pink satin nightie and masturbated, thinking what I'd pack for next weekend and wondering what Sir's house looked like, and if his cock was big and circumcised.
###
I think I'm going to enjoy having Debbie. I had a nice stroking as I thought about his tender little body when I got into bed. I gave the house an extra careful cleaning, Saturday morning I even dug out the gold satin sheet set for my bed. I'd bought a few bottles of wine in case Debbie didn't drink rye, even bought some candles. Nervous energy. What if he's a thief? Performance anxiety? Where is he? Did I leave out a turn on the instructions?
"Ring Ring"
"Hello?...Good. It's the last house on the left in this block. I'll open the garage door, just drive right in, it's the house with the blue spruce in front."
Debbie pulled his car in beside my Lexus.
Oh my God! From that moment on, I've called Debbie 'her'. "Well aren't you the most beautiful little faggot." I blurted it out before I could stop myself. Luckily she took it the right way.
Her hair was divided into two pony tails tied with little pink plastic barrettes. Her makeup was just slightly slutty. She wore a jacket of short hair white fur with long hair dyed purple collar and cuffs on it's cape style sleeves. Her deep purple velvet skirt had pink satin hearts sewn around it's generous knee length hem. Her ankle socks, the kind with the pink lace ruffle around their tops were in pink patent leather flats
###
I blushed "Thank you, Sir." Did you hear that! Sir called me a beautiful little faggot. Oh be still my heart.
I popped the trunk and took the garment bag from of the hook behind the driver's seat. Sir took the suitcase and makeup kit from the trunk, then with his hand on the small of my back guided me into the house.
###
I set her bag down and slipped her makeup kit from under my arm, then hung her garment bag on the hall tree. I took her fur and hung it on a wooden hanger in the hall closet.
Her white cotton blouse had a peter pan collar with pink embroidery that was echoed across the tops of the breast pockets. The top three buttons were undone.
Damn. So sweet and tender looking, and I'd promised myself I had enough will power not to take her until after supper, and it was barely noon. Love that slutty pink lip gloss and finger nails.. I picked up her bags.
"How about the fifty cent tour?"
###
Sir's grey slacks and beige cashmere sweater look yummy. He's in shape, that's for sure.
Nice neat clean house. Three bedroom, two baths. We left my things in one of the small bedrooms. Oo, satin sheets on the big bed in the master bedroom. Modern kitchen, the wall from the dining alcove knocked out and replaced by an island with high bar stools on the dining side.
Sir served sandwiches and coffee for lunch. I was a bit shy. I think Sir was too.
###
We finished lunch. Debbie insisted on helping with the dishes. I let her wash since I knew where everything went. I was stalling. What to do next?
