Black Book Diary Entry Gertrude

Black Book Diary Entry

Gertrude and I worked at the same place and lived not far from one another. We didn't commute together, but gave one another a ride to and from work, whenever one of us was stuck not having a car. She was older than me, but at least 25 years. Matter of fact, her son was my age and her daughter was only a few years younger than me.

Gertrude wasn't a bad looking woman, but I was never attracted to her. She was old. When you're in your twenties either you are turned on or turned off by an older woman and I was just indifferent. I didn't think of Gertrude in a sexual way. We were just friends and co-workers.

Only, I couldn't help but notice that every time Gertrude gave me a ride in her big boat of a Buick, by the end of the trip, her skirt was hiked nearly up to her crotch from her foot going from the gas pedal to the brake pedal and back again. I don't know about you, but it's more than erotic to imagine whatever it is you aren't seeing and I was definitely seeing a lot of thigh.

It doesn't take much to get a testosterone filled man interested. Horny more than interested in her as a sexual partner, when you forget the person and just focus on the individual body parts, I was becoming aroused by her frequent foot action. It had become a game to see how far up her skirt would climb before she reached my house. It took all the control that I had not to reach my hand over and explore her between her legs. I couldn't help but wonder what her reaction would be, shock or wanting more.

I was excited by the fact, but for an inch of material, her panties would have been in plain view. I even tried accidentally on purpose dropping my pen on the floorboard hoping that at that lowered vantage point, I'd be able to see up her short skirt, but no dice. Besides, I was trying to be subtle. I didn't want her to catch me leering. I'd be embarrassed as all Hell, if she caught me looking.

She made me horny by the tease of her shrinking skirt. By the time our ride was over and she delivered me at my door, safe and sound, I had an erection. I started looking forward to those times that Gertrude would pick me up in the morning and take me home in the late afternoon.

"You're car is being repaired again?"

"Yeah, it was making a sound and I didn't want to take the chance of breaking down on the highway."

Things finally came to a head when she gave me a ride home from the company Christmas party. Knowing that I'd be drinking and she didn't drink, I purposely didn't take my car, but had Gertrude drive me instead. Except for her ever so slowly climbing skirt, the ride to work was uneventful but the ride home was hot.

We laughed and joked the entire time at the company Christmas party and, every time that I'd find myself under the mistletoe, she'd find me and kiss me. At first it was a little friendly peck and we'd laugh, until I slipped her the tongue.

I was half being funny and half being serious. I was half being drunk, too. I wanted to know how she'd respond to me slipping her my tongue. Would she pull away or would she slip me her tongue? There was only one way to find out.

To my unexpected surprise, she responded in kind. I couldn't believe I slipped Gertrude the tongue and, more incredibly, I couldn't believe she was returning my kiss. We were French kissing. We were making out. Had I not been drinking, I wouldn't have done that, but I was and I did.

Before I knew it, we were going at one another, as if we were deserted on a desert island. We moved to a dark corner of the conference room and we were making out there. She was old enough to be my mother.

I couldn't believe I was feeling Gertrude's ample tits through her blouse and bra. It felt good. I love feeling a woman's tits through her clothes and Gertrude had a rack. I remember her nipples were hard and protruding from her clothes. She had big, firm tits and she wasn't swatting my pawing hand away, in the way women my age did, a good sign that she was enjoying me touching her, as much as I was enjoying touching her.

It didn't take me long to reach around her and feel her round ass, before moving my hand to the front of her, lifting her skirt, and feeling her pussy through her panties. I was humping her and rubbing my stiffening cock up against her stomach. When I tried pushing her panty aside to finger her pussy, she pushed my hand away. Still, I felt her bush. I touched Gertrude's pubic hair. I'll be jerking off over this for years.

"Let's get out of here," she said. "It's too stuffy in here. I'm hot," she said waving her hand in front of her face. "I need some air."

We got in her car and drove to a more secluded spot. What was hotly erotic before was uncomfortable, now. I didn't know what to say to her. Should I apologize to her? She was old and I was so young. Sitting there feeling a little awkward, she made the first move and she was the one who drove me here and parked her car. I couldn't believe that I was parking with Gertrude.

"We'd have more room to talk in the backseat," she said.

More room to talk in the backseat? As if what I needed to say wouldn't fit in the front seat. That's the line that I use on the women I date. I couldn't believe she suggested that. I couldn't believe I didn't have to coerce her to get in back. What does she want to get laid?

"Okay," I said getting out of the front and moving to the back.

I couldn't help but feel like the female in this situation. Now, I had some insight how my dates felt when I was more aggressive than they may have wanted me to be. She was the one in control.

Somehow, I suspected that we wouldn't be doing much talking in the backseat. Yet, I was hornier than I was drunk and I was eager to explore more of Gertrude's lips and body. She had definitely excited me. I couldn't help but wonder if she sucked cock. Women her age and from her generation were a hit and miss. Some did, but most didn't. I could use a blowjob right about now.

As soon as we closed the back doors, we were making out like teenagers at a drive-in movie, again. My hands were all over her body, and unlike the women my age who would only allow me to take one base at a time without ever having the hope of scoring, Gertrude was running way ahead of me. She was already feeling my cock through my pants. She was the one rounding third base and heading for home.

Oh, my God. I never had anyone do that to me. She was as sexually aggressive as I was. By the time I had her blouse unbuttoned and was feeling her big tits through her bra, she had my pants unbuttoned and unzipped and was holding my cock in her hand. This woman knew exactly what she wanted. She wanted my cock.

"You have a nice, big cock," she said. "I like big, hard cocks. My husband can't get it up anymore. I haven't felt a cock this hard in a long time," she said smiling at staring down at my cock, before looking up at me and kissing me, while stroking me.

I lifted her bra and her tits popped out for me to see. They were a nice size, definitely a full B cup, maybe even a small C cup. As soon as I started fingering her nipples, she was wild with desire. She started stroking me faster and faster. It was obvious she loved feeling my cock as much as I loved touching her nipples and feeling her naked tits.

"Easy," I said. "You're going to pull it off."

"Sorry, did I hurt your penis?"

"Yes, Mommy," I said fooling around. "Now you're going to have to kiss it."

"Maybe I should suck it," she said.

Suck it? Are you kidding me? Gertrude wants to suck my cock? I couldn't believe it. What a sight I imagined it'd be to see my cock in her mouth. Oh, my God, I'd have an overload of jerk off material to last me my lifetime.

I didn't have to ask her twice. She leaned down and took my cock in her mouth. She was hungry for it. She was sucking my cock. She was sucking my cock in the way that she had given me a hand job, with great enthusiasm.

Gertrude was blowing me. I was shocked. I couldn't believe it. Just when I was about to cum, just when I was about to explode in her mouth, there was a rap on the side window. It was the police.

Before she could pull away, before she could react and respond to the police officer standing by the side of the car and peering inside, I exploded like a volcano. Most of it went in her mouth, but a good chunk of it landed all over her face, when she pulled away so quickly. I gave her quite the cum bath.

"You can't park here," he said. "This is private property. Move your car. Now."

Gertrude quickly pulled herself together, while I fixed my pants. She had cum dripping from her face everywhere. She was quite the sight.

Things changed between Gertrude and I after that. She wasn't as friendly to me in work. Matter of fact, she avoided me. Neither of us asked the other for another ride again. I soon found another job in another city and never saw Gertrude again. Yet, having sex with an older and a much more mature woman was a rite of passage memory in my sexual development as a man and a memory that I will always cherish.