Dating Gerald

It's one thing to wake up with an impressive morning erection and realise that you are fifty years old today and you've still got it and quite another to realise that this is the fifth year that you have not had sex.

I threw back the duvet cover and looked at my erection. Still hard, still standing proudly and when I gripped it, still as firm as it ever was. There are some benefits to rarely drinking, not smoking, eating sensibly and walking five miles a day. Pity it never got used on, or in, a woman anymore.

Today is my birthday, I thought, and bloody hell, I’m fifty and it's Saturday so there's no work, nothing to get up for but to go shopping, so how about I set myself a challenge? Four, see if I can manage four.

I looked at the bedside clock. It was oh-five-forty. No rush, but can you manage four in an hour, Gerry-my-lad?

I reached to the bedside table and reached for the ageing bottle of lube that I'd bought myself after previous challenges had rubbed up a sore spot where a finger had chafed against the underside of my cock.

I pulled back my foreskin, exposing my hard dome, darkened with the blood pressurised within it, the skin taut and shining. The rim was dark purple and I watched as the lube that I squirted directly onto the Jap's eye, oozed down the dome and was worked by a few slow strokes, over the rim, into the foreskin and then down the long, veiny shaft and between my fingers.

Anne would have been horrified. Anne, my wife for a quarter of a century of childless marriage, hated the sight of my erect cock. She'd called my suggestion of buying lube to ease and extend our twice-weekly love-making as 'disgusting'.

Well lubed, I started to stroke, picturing as always when I had a wank, Anne. And as normal, I replayed a memory of our love-making in my mind.

It wasn't hard to select which one. Truth be told, twenty-five years of memories and I struggled to maintain ten good shags with Anne as memorable, in my mind. But I'd only ever made love with Anne, I had no other women to remember and our sex life had been extraordinary only in its repetitive vanilla flavour. Over the years, I considered that I had tried, repeatedly to expand our repertoire. I tried to go down on her, had done a couple of times, but she squirmed and pushed me away. She seemed to like it but thought the enjoyment didn't outweigh the inherent disgustingness of the act. Both times she'd made me get up and wash thoroughly, and clean my teeth before I was allowed to go near her. Even then, she'd avoided kissing me for days, until the 'repulsive image of where my mouth had been' faded from her memory.

Similarly with oral sex. I'd soon realised how 'icky' she found 'down there' and how she cringed at even giving me a hand job, so I made sure I was straight out of a long hot shower before I'd even suggested it. A shower, during which I'd denied myself a wank because I wanted to suggest a blow job and didn't want to give her much work to do.

To be fair, she'd given it a go. All her friends talked of it and she didn't consider it weird or perverted, just 'icky'. She'd held me in her fingertips, not wanting to get her whole hand in contact, and put me into her mouth like she was trying a sample of a very hot chilli. Apparently, there had been no discernible taste and she had smiled up at me wanly and cautiously carried on. Four or five times her head had bobbed up and down, moving her lips up and down my shaft just below the glans, and then I'd twitched and having felt the movement of my cock, she'd dropped it as if it was a live eel.

It took several minutes to convince her that I wasn't about to cum and to make her believe my promise not to cum in her mouth. By that time my hardness and enthusiasm were fading and when finally, she did have another go, she recoiled at the first drop of precum and the experiment was over. So over in fact, that I wasn't even allowed to put on a condom and 'finish off normally' until she'd got up, brushed her teeth and used mouthwash.

Still, it was a memory I treasured, and I stroked myself firmly as I replayed the visual memory of a few seconds of my cock in her mouth over and over again, time and imagination adding her enthusiasm to the memory until with a sudden quickening of my hand, I came. In my mind's eye, I came in her mouth and she liked it, in reality, cum arced up into the air to fall back and land in thick creamy strings on my belly.

I looked at it, gave my cock a final squeezing stroke and eased out a final drop, before looking at the cum pooled on my belly. Was Anne right? Was it disgusting? Suddenly, I had to know and for the first time in fifty years, I dipped the fingers of my unlubed hand in my own cum and tentatively lifted some to my lips. I paused. Why? I asked myself. I'd asked her to taste it, to take it in her mouth and swallow it. Is it really that horrible?

My lips closed around my finger and I sucked it clean, pulling my cleaned finger out between my lips and leaving the cum in my mouth. I couldn't taste anything. A bit like my first taste of her, essentially tasteless. I reached down and scooped up as much as I could with two fingers and sucked them into my mouth. I could taste it now. A bit salty, but with no particular taste. If she'd tasted like this when I went down on her, it wouldn't have put me off. Probably an acquired taste, but I could come (cum?) to love it if it was associated with her pleasure. I'd have done anything to give Anne pleasure.

I reached for the tissues on the bedside table and glanced at the clock as I started to mop up. That had taken less than five minutes.

My cock was still semi-hard in my hand and I began stroking it gently, not trying to make me cum, but just stimulating it back toward a proper erection as I decided I’d work forward into what I called my ‘Top Ten’. It had to be of of our firsts.

Anne and I met at university where we were both studying architecture. We were on the same course and both from the north of England, although from opposite sides of the Pennines. She was a shy, reserved Cumbrian, with a strict upbringing and whilst our friends started with sexual encounters that sometimes developed into relationships, we met and became friends, fell in love and edged towards sex.

Anne was conservative in her dressing, staid and old-fashioned some said, and most often seen in a straight skirt, blouse and a cardigan. With all my mates, the first question when discussing a new girl was 'how big are her tits' and with Anne, I really didn't know. A blouse was never unbuttoned enough to reveal cleavage and the cardigans always dampened out any curves. It was weeks before we actually got an evening alone in my digs and when I went to place my hand on her breast, over her cardigan, she firmly pushed me away and said 'No'. That ended that sally of discovery and we spent the evening with nothing more than passionate kissing.

But the next time we were alone, she did wear a T-shirt and there was definitely some breast action going on underneath. I tried not to stare when she casually removed her jumper and moved in for a passionate kiss. I could see the pattern of her bra's material pressed through the tight cotton of the shirt, but when I went to touch her, again she pushed me away. This time she broke the kiss and pulled back as well, pushing her chest forward and looking more impressive than I'd ever seen her. I could feel my erection throbbing in the constriction of my jeans.

"Do you like me?" she asked shyly.

"Anne, I love you," I replied enthusiastically.

"But do you like me, I'm not as big as the other girls, I'm certainly nothing like Pete's girlfriend."

Pete was my flatmate, who was dating an art student, famous for her well-displayed sizeable boobs.

"You are lovely, beautiful," I replied.

And she was. Tall and willowy, with long mousy brown hair, parted down the middle and normally casually pulled back with a hair tie. But when she brushed it out, it shone in the sun, flowed over her shoulders and perfectly complimented her slim form. And she had good hips. 'Breedable hips' my Dad would have called them, in his brash farmer's way of sizing all women up in the same way he did sheep. Would it breed, would it feed and did it have good teeth? But Anne had good legs as well, from what I could tell from what was allowed to show beneath her skirt and what shape showed through her skirt. And from the times I was allowed to rest my hand on her thighs, I had discovered she wore stockings and suspenders habitually too.

"I don't want you to be disappointed," she said as she guided my hand away from her chest. "I'm wearing a push-up bra, it makes them look bigger than they are. But next time, next time I'll wear a normal one and we'll see if you still like them."

"I'll always want to touch you, Anne," I'd declared, quite sure I was being truthful, quite sure that whatever she was hiding under her blouse would be adorable and desirable because I loved her and everything about her.

She'd kissed me then, placing her hand over mine as it rested on her upper thigh and I felt the line of her suspender belt.

And Anne never lied to me then. Not back then. If she said we'd do something I knew it would happen, and when we parted I knew I only had to wait until the the following Thursday night, being as Thursdays were half-price shorts in the student's bar and all our flatmates would be out. On Thursdays, we had the house to ourselves.

And on that Thursday, she arrived, dressed as always in a skirt, blouse and cardigan but when I opened the living room door she turned to me, and took my hand.

"Why don't we go to your room instead?"

I couldn't believe my ears and almost bounded up the stairs, dragging her behind me. And then as I shut the bedroom door, she walked over to my bed, took off her sensible shoes and cardigan and laid down on the bed, her head on the pillow and her hands by her sides.

I whooped and leapt across the room, bounding onto the bed to lay beside her, my head propped up on my elbow and leaning over her, my heart pounding in my chest.

"Calm down, please," she said quietly and I could see she was nervous so I slowly leaned in for a kiss.

As our lips met and parted, my hand hovered above her, not daring to touch her. But then slowly, as our tongues entwined, her hand took mine by the wrist and guided it to her breast.

My fingers shook slightly with the excitement and the first touch of fingertips to her blouse was like brushing an electric fence, but she held me firmly and guided my hand until my palm covered her boob. Cautiously I closed my open hand, my fingers curling until I felt the size of her breast. I was holding it, she wasn't fighting me off and my cock felt like it was going to burst.

Our lips parted.

"Oh, Anne, you're beautiful, so lovely."

She pulled away from me and sat up and I wondered what I'd done wrong, what I'd done to upset her, but slowly she unbuttoned her cuffs and then each button of her blouse in turn. I sat up and we faced each other across the bed. Slowly but surely, she shrugged the blouse from her shoulders and took it off, turning to fold it neatly and place it on the pillow. Anne turned to face me and I got to see her bra and her breasts for the first time.

The bra was unbelievably sheer. Black straps and totally unnecessary underwire, but with black fine-mesh cups that were totally transparent except for a tiny black rose motif. Her breasts were small, beautifully breast-shaped, with absolutely no sag and with tight nipples and shocking dark areolae against her pale, unblemished flesh.

"Wow!" I said, totally speechless for once in my life.

"You're not disappointed? They are very small."

"They are perfect, absolutely gorgeous."

I reached out and traced a circle around her nipple, feeling how firm it was through the lace.

"Wait," Anne, said, and reached behind herself, unhooking her bra and then lifting it off. She sat facing me, totally topless.

"Can I kiss them?" I asked.

She nodded uncertainly and I leant in, cupping one and kissing the nipple of the other, before moving over, kissing her other and then whilst cupping both of them, sucking at one nipple. Anne pushed me away.

"I said kiss, not suck."

"Sorry," I said and leant forward to place a ring of kisses all over one breast, kiss the nipple and then swap to the other breast. "Oh Anne, I want you so much," I gasped, hastily tugging at my belt and then unbuttoning my jeans. My zip moved down under the expanding pressure inside and my erection pushed out, foreskin retracted above the waistband of my black briefs.

Anne stared at it, one arm now covering her boobs as the fingers of her other hand reached out to touch me. The second her finger brushed against my glans, I came, a fountain of cum arching up and landing over the duvet and her skirt.

"Sorry," we said in unison and Anne scrambled from the bed, pulling on her blouse and pushing her feet back into her shoes.

"Don't go," I pleaded.

"I'm sorry," she said a fled from the room.

My mind replayed that encounter like a video running in my head and I recalled the shame and the embarrassment that stopped my chasing after her, leaving her to think she had done something wrong. I remembered that night in exquisite detail, that first sight of her beautiful breasts in all their petite perfection, a love that would never fade for me, and I came again, cum pumping from my cock to flow down the shaft and add to the lubrication of my hand.

I hope you are enjoying Gerald’s tale, I hope you will find it all enjoyable and will leave favourable comments if so. Please leave a review, I value everything my readers write.

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