Chapter 1 – Wishful Thinking?

Monday 23rd March 2015

Durham

Northeast England

I enjoyed a mouthful of coffee as I read the list of names on the screen of my laptop. “It’s almost forty years, and some of the names are clear in my mind.” I had logged in to the School Friends Reunited site for the first time, having discovered it by chance the day before.

At the top of the homepage, right under the site name was a colourful banner:

‘Our First Reunion – Saturday 4th April’

“Do I enrol, and if I do, should I attend the first reunion?”

Reunions had never been my thing. At fifty-four, I wasn’t sure that I wanted to be reacquainted with anyone from my teenage years, but when I saw the website advertised, I had to check out my old school. As I looked at the name of the place, there was a need to know how certain people’s lives had developed from those teenage days. 

 By using the minimum information, if I changed my mind about making any contacts, all I had to do was delete my name from the site. My location, email address, and phone number had been optional, so I’d played it safe, and only used a photo, my name, date of birth, and the dates I’d attended my secondary school. I stared down the list, and chose the names of three girls I remembered as pretty teenagers.

Marie had gone into teaching, and if her features were any indication, she was still slim, but looked older than she ought to.

The second name I selected was Alice, and she had changed dramatically. The lustrous dark hair I recalled was now short and grey. She had gone from being slim and pretty, into a big woman, and was the mother of four boys.

My third selection was the one that made me gasp.

“Jennifer, you are more attractive now than you were as a teenager.” She knew how to use makeup, and her auburn hair tumbled down over her shoulders in loose ringlets. According to the excerpt from her full profile, she was an author, so we had that much in common at least. Unless we were friends on the site I wouldn’t be able to see any more of her profile, or other pictures, but it was tempting.

I went to the boys’ names, wondering if there would be any surprises. The first I chose was Anthony, a guy who had been the top student in the three years I’d known him. He’d joined the Royal Air Force, and become an aeronautic weapons specialist, whatever that entailed. He was handsome, and his profile picture depicted him in uniform, of course.

My second choice was Robert, a guy from the other end of the scale. He had been a troublesome child, and I was stunned to see that he was a senior officer in H.M. Prison Service. He was almost bald, now wore glasses, and had a nasty scar on one cheek, but he’d succeeded in his career.

The third name I selected from the boys was Adam. I wasn’t sure if I wanted to see how he had turned out, but I wondered if perhaps he was the reason that I had logged onto the site. At fourteen, we’d become closer than any of our classmates would have imagined. We were both aware that what we’d done might be considered wrong, and we drifted apart, seeing less of each other in our final year. We never tried to keep in touch after leaving school, and I left Edinburgh to go to uni in Glasgow. If I were honest, I was interested to see what had become of him.

“Oh, my god.” I recognised Adam instantly because apart from being older, as we all were, his features had barely changed. His profile excerpt was accompanied by a second picture, and his impressive physique was emphasised in an athletics vest, shorts, white socks, and trainers. “If I were a woman, I’d be drooling over you.”

I’d had a reasonable life and although I could no longer be called slim, I wasn’t fat, and I didn’t have a beer belly. I went to my profile section, and entered some information about myself.

‘I left Edinburgh a long time ago, and over the years I’ve become a private person, but I doubt if I’m the only one. I’ve never been one for attending reunions, but I felt it would be good to make contact online. The first obvious thing I saw on the site was how diverse our working lives have been, so I’m content to have had a thirty-year career in retail management.

I jog regularly, and I read a lot. Following early retirement, I’ve spent the past couple of years learning the ropes as an author, and my literary efforts are many and various.

If you remember me, I’ll be happy to accept a friend request. Matthew.’

I reread my information, glanced at my profile picture, and hesitated when my cursor was over the log out button. I went back to the Class of ’75, and looked at the names again. I had nothing to lose, so I sent friend requests to Jennifer, and Adam. The worst thing that could happen was that neither of them would be interested in me. I logged out, and sat staring at the screen.

 I briefly thought about how attractive Jennifer had become as she’d gotten older, and for a few seconds I tried to imagine how she might look from the shoulders downwards. If she accepted my friend request, I might find out, because I was sure that she’d have supplied more pictures.

I continued to think about pictures, but my thoughts drifted to how good Adam looked. He’d always been a good-looking lad as a youngster, and judging from his pictures, he’d taken care of his body as he got older. I imagined him kicking off his shoes, peeling off the athletic vest, and shorts, and standing almost naked with his hands on his hips.

I grinned. “He’d look like a porn star, standing there in his white socks, displaying that body.”

I left the school reunion website, but my thoughts were still about Adam’s appearance as I typed ‘Gay porn’ into the search window of my laptop.

Before logging into the reunion site I’d been intending to have a wank while watching naughty videos, and for some reason, gay porn had come to mind. I stared at the list of websites on my screen, and chose one at random. I enjoyed browsing every category except BDSM.

I confirmed that I was over eighteen years of age, and a few seconds later, was faced with a number of thumbnail pictures from videos, all of which had a sub-category underneath. I tried to ignore the pictures, and read the categories, hoping that one of them would catch my eye.

“Crossdressing and Curious … mm, that looks interesting.” I selected it, and was presented with another batch of pictures representing individual videos. There weren’t as many on the screen so I read the captions, and glanced at the pictures, but some of them only showed one person clearly. I clicked on a picture which showed a handsome guy, and an attractive woman with a fuller figure. He was in T-shirt, shorts, and white socks. She wore a short dress, stockings and heels, and her makeup was well-applied.

“James and Cindy … I hope you don’t mind me wanking while I watch you.” I grinned as the credits rolled for a few seconds, and then the pair appeared on screen, sitting on a sofa together. When I heard them talking, I turned the sound down. It was a European language, but I didn’t want to listen if I didn’t understand them. The action got underway rapidly with James caressing Cindy’s face, and then her stockinged legs before he kissed her.

The pair kissed passionately, and explored each other with their hands before James whispered something, and Cindy slowly undressed him. Once again, as I looked at the muscular body in nothing more than white socks, I was reminded of Adam, my boyhood friend. I clicked the small symbol to get full-screen view. As I watched them kiss, I wished that I was taking part, as usual.

I’d occasionally browsed porn over the years, but sex with Caroline, my wife, was so infrequent that porn had become my port of call when I wanted relief. I never failed to find something to arouse me, and though I enjoyed wanking while watching others, I always felt guilty afterwards. I wondered how Caroline might react if she found out about my addiction to such videos.

The camera followed Cindy’s right hand as it roved over James’s body, and my gaze was captured by his long, thick, circumcised cock as Cindy’s glossy red nails contrasted with it. Her fingers spread out, and she stroked the shaft slowly, making it become stiff. As the camera panned back to show both people, James reached under Cindy’s dress and caressed her upper thigh.

The pair continued to kiss, and when James’s hand went farther, Cindy lifted her skirt. Her thick, creamy thighs contrasted with her black stockings, and her black knickers, as James slipped his hand inside to grasp the contents. He paused in the kiss, and smiled as he looked down.

Cindy bit her glossy red lip, and smiled too as her knickers were pulled down, exposing her small, soft cock. I’d had a suspicion about her, but it was a turn-on to see that Cindy was a man, just like James, or me. She helped to get her underwear down, and unhooked from her red stilettos. When they kissed again, the pair continued to caress each other between the legs.

While watching, I felt my own cock become warm and stiff. I continued to enjoy the action as I pulled down my jeans, and boxers, dropping them around my ankles. I lifted my T-shirt, and slowly caressed, and stroked my throbbing shaft.

Meanwhile, the pair on the screen changed from kissing, to taking turns at sucking each other’s dick. The thick shaft between James’s legs responded well to being sucked and stood long and proud. Cindy’s small dick grew a little and became stiff, but wasn’t thick or impressive. At first when James tugged Cindy’s dress up to remove it, I wasn’t sure if the scene would still work for me, but as her thick body, and black bra were uncovered, and her clitty-cock grew, I felt a fresh surge of arousal.

I sighed when James produced a tube of lube, and applied it liberally between Cindy’s buttocks, sliding first a finger, and then his cock into her hole. For a few minutes I slowly stroked my cock as I enjoyed the sight of James fucking Cindy in a variety of positions. The ultimate for me was when Cindy was on her back, her legs held up by James, while he slowly eased all of his big hard cock into her tight pink hole, and leant forward to kiss her.

“Oh, yes … yes, fuck me, Adam … fuck me—” I’d uttered the words as my arousal increased and my arm pumped faster and faster. “Do it … to me … Adam … oh, fuck, yes.” I shot my load with images of me being Cindy, and Adam, my friend from long ago, was James. I stopped working my cock, and it shrunk rapidly, leaving me sitting in my big chair with a belly, and chest covered in puddles of cum. For a moment, I sat there, not feeling guilty as I normally did, but confused.

On the screen, James shot his load inside Cindy, and as it oozed out of her back passage, he followed up by slipping his cock into her mouth. She sucked and swallowed the last morsels of his cream, and worshipped his cock with her lips and tongue.

I closed the website, and sat there for a few minutes longer, my thoughts returning to the clear vision I’d had of me being crossdressed, and being fucked like a girl by my schoolfriend from years ago. I wasn’t sure which of the parts of the scene were more disturbing.

“Am I in denial about my sexuality? Do I really want to have Adam’s cock thrust up my hole?” I looked down at my sticky cum-covered body. “Do I want to be dressed like a woman, and fucked?”

*

Two hours had passed since my glorious wank while watching the porn video. After the joy of shooting my load, and the confusion I felt about what I’d imagined, I’d washed, and got on with a couple of household chores.

I returned to my small study upstairs with a coffee, and sat at my laptop again. I had a new short story I was working on and I always liked to start with a fresh hot drink at the ready. Before touching the keyboard, I stared at the screensaver, and sipped my coffee. My thoughts were jumbled, and I wondered if I ought to delete my name from the School Friends Reunited website. I could watch porn, and nobody would be any wiser, irrespective of what, and who I imagined as a sexual partner. If I got caught up in the reunion website there was the possibility that I’d find it difficult to leave. I might also end up making a contact that I didn’t want to continue.

“I’ll delete my name, and nobody on the site will ever know that I was on there.” I went online, and logged in. I had three messages in my inbox so before settling into writing, I logged in to my mailbox.

 “What the—” I stared in disbelief. It was three notifications from my page on the School Friends Reunited site. “I’ll see what the messages are, and then I’ll delete my account.”

I left my mailbox and checked out the reunion site. The first message was an automated welcome from the site admin, which suggested sending friend requests if I hadn’t already done so. Next, was a friend request acceptance from Jennifer, followed by the notification of a private message, and that stunned me for a moment. 

‘Hi Matthew. Now that we’re friends on here, you’ll be able to see the rest of my profile, and pictures. If you want to be in touch, I’ll be expecting you to post some extra pictures, and assure me that you’re not as shy as you used to be. Jennifer x’

I clicked on her name so that I could have a look at her main profile, and I was rewarded with several pictures of her as a mature beauty with a curvaceous figure. My previous hesitation faded to nothing as I sent a brief reply via a private message.

‘Hi Jennifer. I would like to be in touch, and I promise to upload more pictures. By the way, you were always pretty as a teen, but now you look incredible. Matthew x’

I returned to her profile, and as I feasted my eyes on her, I felt a strong urge to meet her.

***