Waiting alone in the August sun, I had to ask myself if I’d learnt anything at all from my first experience of using an adult dating site seven months earlier.

Sure, I’d asked for his age and more face pics this time, so I doubted “Ed” would turn out to be fifteen years older than me instead of one year younger as he claimed, so that was an improvement on Dave. On the other hand, the car park side of a rural Warwickshire train station was a much more dangerous place to meet someone for the first time than the crowds of Birmingham New Street, especially when no one knew I was here except him. As far as my parents were concerned, I was spending the day back at the University library, doing preliminary research for the dissertation plan due at the start of my third year. I was a diligent student, after all, not a horny boy-slut meeting strangers for sex.

Ed was late.

Just as I was contemplating crossing to the other platform to see how soon I could get a train back home for a frustrated wank instead, my phone rang.

“Hi, it’s me. Sorry, I’m late, I’m almost — oh, I think I can see you!”

An approaching figure waved at me from the path next to the tracks as I put the phone in my pocket. I noticed his hair first: a curly mane that, whilst not Sideshow Bob level, would certainly land him at the front of the queue for the role of Disco Stu at any live-action Simpsons audition. Relief flooded through me as he drew near and my eyes confirmed that his photos were genuine — if anything, they did him a disservice. No doubt he got asked for ID when going to the pub almost as much as me with a face like that, which wouldn’t be mistaken for older than the nineteen that he was, though the broad shoulders and muscular chest evident under his tight green t-shirt probably helped counteract that a bit.

“Hey, Robin, you made it!” Despite being a fraction shorter than me (apart from his hair), if his grin and extended hand hadn’t been so open and friendly, I would have been a bit intimidated by how, well, cool he looked compared to my customary please-don’t-notice-me dark clothes.

“I did,” I replied a little awkwardly but shaking his hand. “I wondered if I’d got off at the right station.”

“Yeah, sorry, Mum took ages to leave the house.” He flashed me another cheeky grin and nodded back the way he had come. “Shall we go?”

Strolling along in the sunshine to a soundtrack of buzzing insects and birdsong, the ease with which our conversation turned to sex surprised me. Unlike some of my peers, I always found talking about anything sexual extremely difficult in person, despite lacking any kind of religious or moralistic upbringing to instill the guilt or shame that others suffered from. It turned out that meeting someone who had read my fantasy of being gangbanged whilst dressed as a girl before even communicating with me made it a lot easier — particularly when he had similar desires.

“So, this is your first time with anyone?” he asked.

“Yes,” I lied, preferring to be the twenty-year-old virgin than admit to the existence of that earlier episode. “How about you?”

“No. I’ve had a couple of girlfriends and had a bit of fun with a friend who’s bi. I’ve never dressed up for anyone though, except my friend Jess who lets me borrow her clothes. Haven’t slept with her, though.”

“She sounds like a good friend.”

“She is! Where did you get the clothes in your photos?”

“Those are all my sister’s, borrowed when she was at school — it’s all I’ve got access to. I want to buy my own, but I can’t bring myself to go into a shop and, you know…”

“I know what you mean. I’m not there yet, either. I want to get there, though. Trannies are so hot!” This was 2004 when trans issues were even less visible than today, so I don’t think either of us knew what a horrible, dehumanising way to talk about transwomen that was. Should I ever build a time machine, I’ll go back and slap us both, but, sadly, that was the language we used. “I really want to be fucked by one. One day, I might even get my own boobs done.”

“Really? You’d go that far?”

“Yeah! You wouldn’t?”

“No. I don’t think I actually want to become a girl, I just… I don’t know. I think I’d have preferred to have been born a girl and like pretending that I was sometimes. Like the Manic Street Preachers’ song.”

“Oh, you’re a Manics fan, are you? Not that big on them myself.”

“Really? Definitely my favourite band by far.”

The conversation went something like that, anyway, until we reached his house. It was a big house, but we didn’t go in the front door. Instead, he led me to a smaller attached building which he called “the barn”. This had been set up as his hang-out room with a sofa, armchair, and table. He put a CD on — not the Manics, sadly, but another band I’ve long since forgotten — while I drew the curtains to hide us from any passing neighbours, and we sat down to continue talking, neither of us quite sure how to make the next inevitable move.

Eventually, Ed couldn’t take any more waiting, and said, “Should I dress as a girl for you, then?”

“If you like, yes,” I replied, not sure what else to say as my awkwardness flooded back.

He picked up a bag and left the room, leaving me to fidget in anticipation — nervous but excited. All sorts of thoughts ran through my head — running out on him, what we might do together, and so on. Feeling hot, I took my hoodie off leaving me in my black Queenadreena t-shirt. Despite being labelled large, I suspected the fit was not intended for a male figure — the closest I came to dressing femme in public.

I heard footsteps, and Ed came into the room, wearing a tight pink skirt and white singlet, looking incredibly attractive with it stretched over his pecs, if not especially feminine. As he sat down again in the armchair, I was struck again by how broad his shoulders were and how generally toned he was. Pressing against the taut front of the skirt, I could just make out the shape of his erection.

“What would you like your slut to do, then?” he asked after a pause. Yes, he really said that — so it was difficult to know what to say in such an artificial situation.

I didn’t even try to be clever and simply replied, “Let’s start with some oral.”

Ed obediently knelt between my legs. I quickly unbuttoned my fly and pulled my jeans and boxers down, and he took my limp cock in his mouth while I kicked off my shoes. His tongue was hot and wet on my hardening dick, so I pulled my t-shirt off too, and touched his frizzy hair as he bobbed up and down on me. It felt great, of course — blowjobs have to be pretty shit to feel bad — but I wanted his cock and began reaching further and further down.

“Want to try a sixty-nine?” he asked, pulling away when I began leaning right over him.

“Yes, please,” I said, the lust evident in my eyes.

“OK, but you’ll need to free me first.”

He stood and I eagerly got on my knees to fumble with the zip on his skirt. Pulling it down off, his hips revealed black lace knickers with his hairy balls poking out the side. Knowing I was no better at containing my bits in feminine underwear, I made no comment and nuzzled into them eagerly, but before I could get carried away, he pushed me back.

“Get on the sofa so I can have your cock, too.”

I obeyed and lay on my back while Ed got on top of me, adjusting his position until he could suck me and he was within my reach. Holding his legs, I hugged him closer and pulled his foreskin back to get at the smooth head. Gingerly licking at it with the tip of my tongue, all those little doubts about whether being bi was just a fantasy dissolved with that taste of precum. He hardened as I slathered his silky skin in saliva before sucking him into my mouth, taking the head all the way to the entrance to my throat. It was just as I had practiced with toys, only easier as he was neither as long nor as girthy, and far more delicious.

Although he got harder, he didn’t grow much bigger, so I threw myself into sucking his whole length. My lips slid over him from the tip to the base so that my nose pressed deep into his balls, and then back again. I got so into it that I barely noticed his mouth on mine until I paused to catch my breath. Shuddering slightly from the combination of pleasure and danger when his teeth dragged lightly over my shaft, I began licking his balls, flattening his pubic hair and tasting the salt of his sweat. Just when I was about to start sucking his dick again, he got up to turn the music off.

“Would you like to fuck my arse?” I asked him as I knelt up, the coyness of my tone belying the bluntness of my offer.

“I can hardly say no to that, can I?” he replied. “You want any poppers first?”

“No, thanks.” I vaguely remembered poppers from school drug awareness classes but had never been tempted to investigate why gay guys used them so much. The risk of having to explain to my parents how I got chemical burns around my nostrils during a trip to the library put me off exploring that day. “I’ve brought plenty of lube, though.”

I reached into my bag for a tube of KY jelly, squeezed a dollop into my palm to spread on my shaved hole, then eagerly reached for him.

“Oh, wait a sec!” he said and leaned back towards the stereo. As Ed ripped open the condom packet he’d just retrieved, I realised with relief that this really was going better than my first time.

Once the protection was on, I spread lubricant on his latex-coated dick, my fingers trembling slightly, and turned to face the wall. Gripping the back of the sofa harder than necessary just to support myself, I pushed my bum out towards him, words staying stuck in my throat. The head of his cock tapped at my entrance, the only sound other than our heavy breathing and a car passing in the street outside, while he placed a hand on my hip to steady me.

Slowly, he began pushing it in, and I pushed back, wishing I’d used my dildo in the weeks leading up to this to be more prepared and relieved that he did not in fact have the monster-cock of my wet dreams. Little by little, he edged his way inside, until his hips pressed into my buttocks. Greedily, I wiggled back, but he was the stronger out of the two of us and held me still. He adjusted his stance, pulled halfway out a couple of times to my satisfied groans, and began thrusting enthusiastically, so I closed my eyes and let him take control.

My muscles quickly adjusted to him once I relaxed — too well, perhaps, as I found myself longing to feel stretched. Not only that, but he kept pulling back too far and slipping out, interrupting that addictive, rhythmic slapping of flesh. I tried to help him by reaching back to catch him when he did, but the third time this happened, he stepped back.

“Let’s try another way,” he suggested, a touch of irritation in his voice. “Lie on your back.”

I did as instructed and brought my legs up to my chest, imagining myself as the woman in a porn video, even if Ed was the one dressed for it. Now just in a bra, he supported himself on his strong arms above me and entered me again while I craned my neck to watch. A gasp escaped my lips as the bulbous tip slid over my prostate at just the right angle, and my head dropped back.

When he grabbed my softened dick and started pumping it in time to his thrusts, I looked up again and smiled weakly at him, but neither of us spoke. Even getting fucked like a pornstar wasn’t enough to break my shyness and get vocal like one.

“Oh fuck, I’m gonna come soon,” he murmured, breaking the silence. “Too soon?”

“No.” I shook my head. “Come when you’re ready.”

Moments later, he gasped and slammed inside me as his balls emptied. Watching his face contort in orgasm, I suddenly craved the taste of come and wished I’d asked him to cum in my mouth. Soon after, he withdrew from me, his dick softening and the full condom dangling from the end. After dropping that in the bin, he knelt on the sofa and assumed the pose I had been in earlier.

“You want to fuck me, now?” he asked, wiggling his butt cheeks at me.

“Definitely!” I replied, a little surprised he didn’t want a break first since I usually get a sudden drop off in libido after any climax.

I took out the condom I had brought and put it on while he lubed up his arse, and then spread KY jelly on my shaft, massaging it to get it hard, and got into position. Pressing my glans down on his hairy hole with my thumb, I pushed my hips forward, and… my cock slipped out and up toward his back. With a nervous laugh, I shuffled back and tried again, getting the tip into his star. Relieved at that achievement, I thrust forward, but this time, Ed jerked forward with a yelp.

“Slower!” he said. “You’re massive!”

“Sure, sorry.”

His compliment, which I thought was a bit exaggerated, didn’t counteract my nerves, and as I slid my slimy length between his buttocks, I could sense the steely hardness melting away. I tried to enter him one more time anyway, but now I was so soft the shaft just bent. Ed took pity on me and stood up.

“It’s OK, Robin, you just need to prepare me a bit first when you’re that big.” Reaching into his bag, he pulled out a silver vibrator —the classic bullet-shaped one from thousands of porn videos — and grabbed a small bottle from next to the stereo. “Here, let me show you.”

Settling into the armchair in the corner, he took a sniff from the bottle of poppers. Mortified, I handed him the tube of KY and sat on the corner of the sofa nearest to him. How many times had I fucked myself with dildos, both manufactured and vegetable? I knew how to prepare myself for anal, so I really shouldn’t have needed to watch him gradually work one, two, and then three fingers into his hole like this, but I’d let nerves and horniness turn me selfish. Luckily, I didn’t know much about anal safety back then, so the complete lack of a flared base to the toy didn’t fill me with fear of a potentially embarrassing hospital trip if he lost his grip and it got sucked up inside. At the time, it was kind of hot watching him push that silver dong inside himself and meet his eyes as he slowly thrust it in and out, and I stroked myself in time with him to coax my erection back to life.

“Ready to try again?” Ed asked in a voice that wavered a little from the pleasure he was giving himself.

“OK,” I said meekly, still embarrassed but keen to finally be on the giving end of anal.

He knelt up and bent over, holding on to the arm of the chair, and I went behind him for a final attempt. I lay my dick on his crack, but I was still too soft, so I pumped it furiously, silently urging the blood to pump back in, but to no avail. Frustrated, I pushed the tip against his hole anyway, and he did his best to open up and encourage me.

“It’s no good,” I said, stepping back and yanking off the condom, accepting it was a lost cause. “Sorry, um, I—”

“Hey, it’s fine!” he said, smiling reassuringly. “There are worse reasons for not being able to have sex than your dick being too big. I’m kind of jealous.”

I smiled sheepishly. Compliments about my cock were common on the sites I’d been using, to the point that they had become monotonous, and I still thought he was exaggerating, but, well, I did like my cock, and it took some of the sting out of my humiliation.

“How about I suck it instead? We know it fits in my mouth.”

“Um, OK.” I must have been really embarrassed to hesitate at the offer of a blowjob.

Ed got down on his knees and took me between his lips again, and then pulled back, giving a short laugh and shaking his head.

“It really is big, you know,” he told me, stroking it to get rid of the latex taste. I smiled weakly, unsure how to respond. As I watched him suck me and settle into a rhythm, I began to relax again. The sound of his slurping and hummed appreciation filled the small room, and after a couple of minutes, I was rock hard once more — hard enough that we could have tried for anal again. Though tempted, I decided not to suggest it as the condom I’d bought now lay discarded in the bin and I didn’t know if he had any others handy.

“That feels really good,” I murmured in an effort to return his earlier encouragement.

He looked up and sucked harder, swirling his tongue around the head every time he pulled back, drawing a little gasp from me each time. Placing my hands on his curly hair, I closed my eyes, no longer worrying about impressing him with my stamina but letting the sensations take over and the pressure build.

“I’m going to come,” I warned him, not sure if he wanted me to do so in his mouth, but he just intensified his efforts.

With a gasp, the orgasm flooded my head and his mouth. He kept sucking, prolonging the climax and increasing my pleasure even more. As it began to fade, I looked down and could see drops of cum falling from his lips to splatter on the floor.

“How was that?” he asked, getting to his feet.

“That was fantastic,” I told him after a shocked pause, and he laughed. Still recovering, I looked around, and Ed passed me a tissue to clean up.

“What time’s your train?”

“I think there’s one at about two-thirty.”

“OK, that gives us about… an hour and a half. Time to get something to eat — I’m starving.”

Once we’d cleared away the mess and the condoms, we both got dressed in comfortable silence, until a knock at the door made us both freeze in the middle of putting our shoes on.

“Ed, are you in there?” A female voice called out.

“Yes, Mum, just a moment!” He rolled his eyes at me and went to the door, slipping out and closing it in a classic, guilty teenager hiding something from his parents' move.

Trying not to laugh, I gathered all my belongings and waited. Clearly adept at manipulating his mother, the conversation never got loud enough for me to hear and ended with a single set of footsteps walking away on the gravel. A minute later, once he was sure she was out of sight, Ed returned.

“It’s alright, I said I was going into town to meet Jess. She’ll want her clothes back, so it’s not a lie. Come on.”

Emerging back into the sunlight of Middle England suburbia after the activities of the previous hour felt surreal but oddly satisfying.

“That was really fun,” he confessed as we walked into town. “Different to being with a girl. I have been with one other guy, which was interesting, but this really hit the spot.”

“You definitely hit my spot,” I said, making him snort. “Sorry, I couldn’t fuck you, though.”

“Hey, I still got to be a slut on my knees sucking your cock, and got to fuck you. I’d say, ‘next time,’ but you’re going away, aren’t you?”

“Yeah,” I said, feeling a twinge of regret that wouldn’t be able to meet up with him again anytime soon. “Compulsory year abroad as part of my degree.”

“Oh, poor you,” he said sarcastically. “Send me a message when you’re back, though,”

Reaching the busy town centre forced our conversation to less horny subjects, and then I blinked and was on the train back home.

When I lay in bed that night, thinking back over everything that had happened, I experienced none of the conflicting feelings of self-disgust that had overtaken me with my first time. Although full of awkward, embarrassing moments, it had been a good day. It didn’t improve my self-confidence enough to make a move with anyone in real life, of course, or even online for the next year, so I was still far from the boy-slut I dreamed to be, but I could at least feel comfortable telling my housemates that I liked both men and women.

That was a good start.