Gwen & Robert, Old Guy, Young Gal

I was half an hour early, when I arrived at Gwen's house. Actually, having left work early because all I could think of was being alone with Gwen, I had been ready since six. I parked my truck by her car, a red Mustang GT convertible. The car looked fairly new, and I wondered, how a waitress working in a two-bit diner can afford a forty-five thousand dollar car, when it stretches my budget just to buy gas for my truck. I walked up her front steps and rang the bell.

"Come in, Robert," she said from somewhere upstairs. "The door is unlocked."

"Hi Gwen," I said not knowing where she was and what else to say, when what I typically say to her every morning is, "Hi Gwen, I'll have the usual."

"Coffee and toast," she mumbles back, while writing in her book.

"I'll be down in a minute. There's coffee on the counter and beer in the fridge. Help yourself, Robert," she said. I loved how she said my name. Rolling off her tongue, as if my name was an endearment, she made me feel so special, whenever she called me by name.

Passing up a beer for a cup of coffee, having missed my afternoon coffee break to leave work early, definitely, I didn't want to fall asleep halfway through this date, if that's even what this was. With my luck, she asked me out to dinner to sell me some Tupperware or a yearly week at a timeshare. I poured myself a cup hot, black coffee and wandered around her living room. She had pictures everywhere, mostly of her growing up in this house. Always a pretty girl, she turned into a beautiful woman. Even though I was thrilled that I was standing here in her house, Gwen's house, I couldn't help but wonder why? I'm nothing special, just an average guy and Gwen is my real life movie star masquerading as a waitress in some hole-in-the wall, dump of a diner.

"God, she's so pretty," I said mumbling to myself. "She's the prettiest woman I've ever seen."

"Thank you," she said.

Standing right behind me, while looking over my shoulder, I never heard her come down the stairs.

"Wow. You look so much better in person," I said putting down her picture and laughing at myself.

As if I had chosen her outfit, she made the perfect fashion selection, a short shirt and a low cut button blouse. I figured that Gwen was 5'7" tall, but with the 2" heels she was wearing, she was almost my height. Honestly, funny how my mind works, when a beautiful woman is wearing such a short skirt, but I didn't know how she was going to get in her Mustang without flashing me her panties. Honestly, I didn't know if I should nod my head, shake her hand, or dare give her a hug. Instead, she took the lead, pressed her shapely body against mine, and gave me a peck on the lips, before hugging me, really hugging me, as if we were long lost cousins.

Oh, my God. Gwen kissed me. I mean, it wasn't a real, tongue down my throat kiss, but it was a kiss and it was from Gwen. I'll be thinking of this tonight later, when in bed with my bad self and my hand firmly around my cock and stroking myself, that's for sure.

"Are you ready?"

"I am," I said guzzling my coffee, as if I was drinking liquid Viagra.

Being the gentleman that I am, albeit the perverted gentleman that I'll always be, I opened her car door, while hoping she'd flash me her panties. With her legs nearly spread wide open to get in her car and her short skirt nearly up to her crotch, she didn't disappoint me. As if my eyes could move in two different directions at the same time, one eye looked down her low cut blouse at her exposed bra and cleavage, while my other eye was rewarded with a bright, white patch of her panty. Damn, she was so hot. She was so sexy. Thank you, Jesus for giving me sight!

"Well, what do you think, Robert? Are you ready for my life story?"

"I am," I said.

"I'll tell you all about me, once we get our food. I'm hungry, starving actually. I haven't eaten anything since lunch and that was only a bowl of chicken soup and a couple of crackers. Sorry, but I can't think on an empty stomach," she said driving out of the city.

"Nice car," I said giving her a look, as if asking her how she could afford it.

"It was a gift," she said.

"Oh?"

A gift? Who gives a beautiful woman a brand new Mustang GT convertible, as a gift, without expecting something sexual in return?

"Daddy bought it for me, when I graduated college with my master's degree."

Master's degree? Daddy? I wondered if Daddy was her father or if Daddy was her sugar daddy, some 80-year-old man, who was drooling over her, in the way that I was drooling over her now.

"What's your field of study?"

"Art history slash English literature, which is why I work as a waitress," she said with a laugh. "I thought I wanted to teach, but I changed my mind. I really don't like kids, especially someone else's kids," she said with a laugh.

It was then that I wondered if she prostituted herself on the side. Maybe she thinks I have money. Maybe she thinks that I'd buy her a gift, too. For sure, if she asked for a thousand dollars to have sex with her, I'd go to the nearest ATM. Only, I think my bank has a three hundred dollar limit. Matter of fact, I don't think I even have three hundred dollars in my bank. Linda took whatever I had saved. I wondered if she'd take a check, debit card, or credit card. I'd sell my soul for a naked, sweaty night with Gwen. Then, I realized, way ahead of myself and no different from all those other men leering at her from across the restaurant counter, that we were just going out for dinner. This wasn't a real date, was it?

"I know this place. It's not much to look at, but they have the best fried clams. Do you like clams?"

"I love clams," I said, suddenly thinking about sniffing, fingering, licking, and fucking her raw clam.

She headed in the direction of the ocean and it was about a twenty minute drive, but we made it there fifteen minutes before they closed. Hoping for an encore, I hustled around the car to help her with her door. Only, this time, she denied me the pleasure of a panty flash by getting out of her car herself, before I could clear her bumper.

Once we got our food, she parked in a more secluded spot, a spot that I would have chosen, if I was a horny teenager in a red, Mustang GT convertible with a beautiful woman. Only, within full view of the Atlantic Ocean, I wasn't understanding why this gorgeous girl was parking her car in a spot that was just as desolate as it was romantic. I wasn't some twenty-something-year-old stud. I was nearly old enough to be her father or wicked older brother, anyway.

It was then that I wondered how old she was. Bad enough that I was ten years older than Linda, not so much of a difference now, but it was a real issue to her parents and her friends back then, when she was barely twenty-years-old and I was nearly thirty-years-old. Maybe Gwen is older than I think she is. Maybe, if I can't get with Gwen, she has an older sister. Looking as if she's twenty-two, if she had six years of college, she's at least twenty-four, maybe even twenty-five. Definitely, in the way she looks so young, she can't be more than twenty-six.

"Can I ask you a personal question?"

"Oh, oh. Here is comes. You want to know if I'm married and have kids or why aren't I married and have kids?"

"Actually, in our talks at the diner you told me you're not married or attached and don't really like kids," he said with a laugh. "I was just wondering how old, or in your case, how young you are."

"How old do I look," she said turning her head to me, while batting her long eyelashes.

"I'm afraid to know but if I was to hazard a guess, I'd say twenty-two?"

"Twenty-two? Thank you. You're too kind."

"Then, I figured, because you've had six years of college, twenty-six."

"Twenty-six? Thank you again for your kindness," she said with a melodious and endearing laugh that made me want to kiss her.

"I can't imagine you being any older than that. You look so very young," I said, "sinfully young."

"I'll be thirty-two in July, July 26th. I'm a Leo."

"Thirty-two? Wow! I never would have guess you were thirty-two. You could have knocked me over with a feather. I'm shocked."

"Why?"

"Because Linda was ten years younger than me and with you, I felt as if I was a dirty old man," I said with a laugh. "That is, if this is a date."

"A date? Did you really think this was a date?"

My heart sunk in my stomach, when she said that. Feeling so embarrassed that I'd dare even think that someone like her would be interested in me, I was devastated. If it wasn't a date, then I didn't know what it was. Maybe it was just as what it appeared to be, two friends having dinner. I was so disappointed. Here I was expecting a big evening and this isn't even a date.

"It's not a date? I'm so embarrassed. I just thought--"

"It is a date, you big dummy. If I waited for you to ask me out, I'd still be serving you breakfast," she said with a laugh. "Honestly, I didn't know what else to do to get your attention. I practically served up my big boobs to your face, when leaning over the counter to talk to you. I saw you looking down my blouse, you pervert," she said with a laugh. "Still, even after flaunting my body before your eyes, you never asked me out. Why?"

"Why? Gees, Gwen. Look at you and look at me. You're so beautiful and I'm so...old."

"You're not old, Robert. You're wonderful."

"Thank you."

We spent the rest of the time together talking, while making eyes at one another. I so wanted to kiss her, but I didn't have the nerve. Here I go again. Afraid to ask her out, now I'm afraid to kiss her.

As if the food was an aphrodisiac, the clams were unbelievable. Being with her in the car, my senses were heightened. Everything smelled, looked, and felt better, when sitting there with Gwen. The batter just melted in my mouth and, after being accustomed to the tough, dried out clams they gave a Friendly's, these clams were succulently tender.

"You don't mind if I put the top up, Robert, do you? It's getting a little chilly."

"No, not at all." After she put up the top, she surprised me, when she opened her door. "Where are you going?" Had we already eaten our food, I would have figured that she wanted to walk along the beach and I'd be willing to do that, so long as I could hold her hand or put an arm around her shapely waist, while pretending that she was my woman.

"We'll be more comfortable in back," she said moving her seat all the way forward and flashing me her panties again, when climbing in back with her legs parted nearly as wide as they were, when she got in the car before.

Being that I'm six foot tall, I didn't think that I could fit in the backseat of a Mustang, even with my seat all the way forward, but I did. Actually, if I had to cut my feet off to fit in the backseat with Gwen, I gladly would have.

"Well, this is cozy," I said.

"You don't mind," she said reaching down to remove her shoes, "do you? I should have known better than to wear heels, after standing on my feet all day. My feet are so sore," she said rubbing them.

"No not at all," I said. "Make yourself comfortable." You don't mind if I take off my pants, do you? I thought of saying but didn't.

"Oh, that feels good," she said stretching out her legs and depositing her heels in my lap. "My calves ache."

Oh, my God. Does she know her heels are in contact with my bulging cock? If I didn't have an erection from seeing her panties twice, I surely had one now that her panties were in continue view of my horny eyes, while her feet rested on my growing prick.

"Nice stems, Gwen," I said looking down at her shapely legs and seeing that her panties were still exposed. I waited for her to pull her short skirt down, but she didn't.

"Thank you," she said looking down at her legs. "Maybe after eat, I can sweet talk you into giving me a foot massage."

A foot massage? Forget about a foot massage, I'd love to give her a head to toe massage.

"Sure, I'm the master of foot massages," I bragged, even though I've never given anyone a foot massage, while resting my hand on her foot, before reaching up to massage her shapely calf.

We ate and we talked, all while Gwen occasionally and unconsciously, no doubt, wiggled her heel over the head of my erect prick. Maybe this was the foot massage she was talking about.

"Be a dear, Robert and rub my poor feet," she said opening her legs wide enough to give me more of a view of her panty clad pussy mound, but not wide enough for me to think bad of her.

"How's that?"

Lifting up one leg to massage her foot, while exposing more of her panty, I rubbed one foot, before rubbing the other, she laughed with glee, when I did that. Each time I lifted her leg and massaged her foot, her legs opened wider and skirt climbed higher. Expecting her to notice her panties were so exposed, when she didn't pull down her skirt, I continued giving her a foot massage, while gazing up at her panties and hoping she didn't catch me looking. I couldn't believe that I had a constant and continual view of Gwen's panty clad pussy. If nothing else happened during this date, I'd go back to my lonely life a happy man.

Back and forth, I took her feet in my hand and massaged them. She closed her eyes and put her head back against the side of her car and, as soon as she closed her eyes, I reached up to massage her calves, while staring at her panties. My fingers were so close to her panty clad crotch that I wanted to reach out and cup her pussy, after tracing her pussy slit with my finger and rubbing her clit through her panty. Afraid to go any higher, I so wanted to massage her shapely thighs, before massaging her between her legs. Then, encouraged by the sight of her panties and the fact that her eyes were still closed, as if she was napping, I reached my hands higher and massaged her exposed shapely, firm thighs.

"Wonderful, That's just wonderful, Robert. I swear, just by massaging my feet, my calves, and my thighs, you could ask me to do anything and I would," she said opening her eyes to make eye contact with me, while giving me a sexy look.

Anything? She'll do anything for a foot, calf, and thigh massage? While thinking of her sucking my cock, I massaged her feet and legs, as if I was massaging her breasts and ass. Maybe from watching Pulp Fiction one too many times, I made foot massaging moves that I didn't even know I knew. Within just a few minutes, I had her moaning, as if she was having an orgasm.

"Are you okay, Gwen?"

"Okay? I'm better than okay," she said removing her feet from my lap and sitting up, while giving me another flash of her panty, this time a bent, open legged flash. My feet feel wonderful and I feel so relaxed. She looked me square in the eye and as if she was Marilyn Monroe or Kim Basinger, before breathing out her lust for me, "Since you've given me so much pleasure, is there anything that I can do for you, Robert?"

Aside from the long laundry list of sexual things that I wanted to ask her to do, unzip my pants, pull out my cock, and stroke me, before sucking me, I was afraid to tell her what I really wanted was sex. Still, putting my fear aside, I took a deep breath and summoned my courage to take the my first baby step in bedding Gwen.

"Well, if you don't think me too forward, I always wanted to kiss you."

"You've always wanted to kiss me? Why didn't you? With my face planted inches from your face, with my lips reaching for you across that dining counter, I've been waiting months for you to kiss me."

"You have?"

"I've always wanted to kiss you, too, Robert. As long as I live, I'll never understand men. Some men, need only a look for them to stalk you and others need a baseball bat to the back of the head for them to notice you. You fall in the latter category, instead of the former," she said leaning into me and pressing her breasts into my chest, while attaching her red lips to my horny lips.

Without even having to sneak her my tongue, she wrapped her arms around my neck and filled my mouth with her tongue. As if her breasts were magnetic and my hands were made of metal, my sweaty palm felt her abundant breast, while she kissed and kissed me. I was kissing Gwen. I couldn't believe that Gwen was kissing me, while I was feeling her tits through her blouse and bra. Immediately, her nipples pushed against my palm and I could feel that they were big ones. Between her flashing me her panties, the foot massage, and now the kissing and groping, I was in Heaven. If I died now, I'd die happy. By far, she was a much better kisser than Linda. By far, she had much bigger and firmer breasts, too.

Unable to wrap my brain around all that's happened so fast, I couldn't believe I was sitting in the backseat of a Mustang kissing and feeling up Gwen. Shades of what I did twenty years ago with my dates in my Camaro, before I married Linda, I was now doing with Gwen. I couldn't believe Gwen was allowing me to feel her breasts, while French kissing her. Going for broke, I unbuttoned one button of her blouse and looked down to see what I could see, while waiting to see what she'd do, before unbuttoning another button. She gave me the green light, when she kissed me more passionately, while reaching down to feel the tent pole in my pants. Something I always fantasized her doing, while masturbating, Gwen was fondling my cock through my pants, as I was feeling her breasts and fingering her nipples through her bra. Taking her lead, I went up her short skirt and felt her pussy through her panty. Oh, my God. Was I going to get lucky tonight? If I was a betting man, I'd bet on me.

"If you lick my pussy," she said breaking off her kiss to whisper in my ear. "I'll suck your cock."

This isn't happening. I'm dreaming. I can't believe Gwen just told me she'd suck my cock, if I licked her pussy. Having known her for months, always fantasizing her talking like that to me, I never heard her say an inappropriate word, until now. With no downside to that agreement, licking her pussy, before she sucked my cock, was a win/win for me.

"I'd like nothing more to eat you. I so want to lick you. I can't wait to remove your panties to finger you, Gwen, but unless I stick my legs out the window--"

"We'll go to my place, silly," she said laughing and giving me a kiss before climbing in front.

The drive to her place was only twenty minutes, but it was the longest twenty minutes of my life. We talked but I don't remember what she said or I said. All that I could think about was that I was going home with Gwen to have sex with her. My dream come true, I'll never ask God for anything for the rest of my life.

As soon as we got in her house and closed the front door behind us, we were all over one another, as if we were horny teenagers. Kissing and kissing and kissing, I've never kissed any woman as much as I kissed Gwen that night. She was topless and she had my cock sticking straight out of my pants, by the time she took me by the hand to her bedroom upstairs. We were both naked, before we even hit the bed. Never have I been as excited and she was so wet.

Immediately, I fell between her legs and fingered her, while licking her. I've eaten a few pussies in my life, but Gwen's pussy was the best pussy I ever had in my mouth. Forever ruining me for other women, if she let me, I could make a steady diet of her pussy. With my tongue and fingers buried in her cunt, I loved watching her squirm, while listening to all the wonderful sounds she was making. I was about to make Gwen cum with my mouth and fingers. Any second now, Gwen, the woman of my dreams was going to cum in my mouth and then she did.

"Oh, Robert! Oh, my God! Oh, my God! Don't stop. Please, don't stop. Oh, yeah, right there. That's it. Right there."

As soon as she tensed her thighs and curled her toes, I knew she was done. Only, I continued licking her and ate her again and didn't stop, until she had another orgasm. With Gwen all over my face, we kissed. Covered in her sweetness, she seemed to enjoy licking my face, as if she was a new puppy and I was her master.