Chapter 1 – Programming Keith

Sunday 18th October

“I’ve wanted to see Amsterdam for ages, so I’m just excited to be going there. It will be great hiring a bike and heading wherever I like when I have free time from the studio.”

The three of us sat around the kitchen table as we managed to do at least a couple of times each week, and usually at the weekend.

Keith said, “What are you looking forward to the most on your trip, Dennis?”

“You’ll have to visit the Red Light district so that you can tell us if it’s as good as people say.”

“I might—” Dennis grinned.

“Dennis,” I said, “just do it, and if anyone from the studio asks if you’ve been there, you say that your friend Keith is sex-mad and asked you to check out the Red Light district and the sex shops.”

Keith laughed and turned to me. “I bet if you went to Amsterdam, you’d check out the girls in the windows.”

“Maybe,” I said, and the other two burst into laughter.

“Whatever you do, Dennis,” Keith said, “you take advantage of your week away, mate.”

“I will, thanks, Keith.”

Keith and I were taking advantage of our friend’s week away. Of course, we would both be doing it for different reasons and in slightly different ways.

Dennis said, “Have either of you got anything lined up for the coming week?”

Keith said, “I’ll be working today and probably a couple of evenings through the week, but I’ll be practising being my usual charming self.”

“The girls around here don’t know what danger they’re in with you around.” Dennis laughed.

“I just pretend to be all macho around girls,” Keith said. “I’m really very sweet with a girl, and if they want to, I let them lead the way.”

I said, “You really are a charmer, Keith.” I turned to our mutual friend. “Hey, Dennis, wouldn’t you love to be a fly on the wall when Keith is entertaining a girl in private?”

“It sounds a bit kinky, watching your friend with somebody, but it might be fun.”

Keith said, “You two are just a pair of kinky voyeurs.”

I said, “I bet you’d be happy to watch a couple of people getting it on.”

“Well … maybe, if it was kinky enough.”

We all laughed together, and then our conversation became normal until breakfast was over.

* * *

“Right, guys,” Dennis said, “my taxi for the airport is outside, so I hope you don’t miss me too much.”

“Have a great week,” I said.

“Yeah,” Keith said. “Don’t worry about us being stuck back here, mate; we’ll get by somehow.”

We all laughed again.

“I’ll see you next Sunday evening. Bye.” Dennis lifted his case, laptop bag and went downstairs.

Keith closed the door and turned to me. “Eddie, you have no idea how much you’ve changed that guy, and it’s all for the better.”

“I know he’s happy to go out socialising now, but—”

“No buts—he’s a different person to the guy who lived here before you arrived.”

“Thanks,” I said. “I’m having a brew if you fancy one.”

“Yes, I think I will, mate. Shall we sit in the living room?”

“Yes, and then I suppose we’d both better get some studying out of the way.”

Five minutes later, we were sitting in the living room enjoying a coffee.

Keith said, “What have you got lined up for today?”

“Not much. I’ll do some work on my projects until lunchtime, and then after we’ve eaten and you go to work at the bar, I’ll go for a walk in the afternoon.”

“That sounds like a pleasant day, and I can’t really complain; I enjoy the shifts in the bar.”

We were both quiet for a few minutes, and I broke the silence. “Do you really think that Dennis has changed since there have been three of us living together?”

Keith nodded. “Like I said earlier, he’s a different person. He’s more relaxed, and he says things now that I could never have imagined him saying.”

“Like what?”

“Strangely, it’s things like this morning when we were talking about Amsterdam … and sex … and, of course, remember, it was only because of you that he attended that fancy dress function.”

“Maybe he’s one of these guys who just need a little nudge now and then, you know, to get him trying new things.”

“Dressing up as a schoolgirl is not just a new thing—it must have been a massive step for him. I know it was for you.” He smiled. “Do you know what I find strange?”

“What?”

“I was trying to spot you two in the function room that night, and I couldn’t do it. I remember thinking that it would be easy, even though you both said you were keeping your identities secret.”

“Why did you think it would be easy?”

“Well, as I expected, a lot of the guys didn’t look that much like girls—they stood out by the way they moved and the way they walked, and, of course, a lot of them were drinking pints of beer.” He sipped his coffee. “I studied plenty of the fake schoolgirls, and it was about halfway through the evening when it struck me that quite a few guys were getting right into character. A lot of you were avoiding the beer and drinking something more ladylike, and you two must have been practising the walk and the deportment and other stuff.”

“When we got dressed that evening, I suggested to Dennis that if we were going through with it, we should give it every effort. I think he actually enjoyed it once we got underway.”

“I’ve just realised something that I should have remembered that night.”

“What’s that?”

“Dennis is quite … well, he’s chubby but not a bad-looking guy, so it would have been easy to spot him if he was wearing a skirt. I do like a nice pair of legs, and I know you’re partial to a girl with a bit of puppy fat. You’d probably have fancied Dennis as a schoolgirl.”

I wanted to say something, even though it was risky. “I’ll be honest with you. When I saw Dennis dressed and transformed into a sixth-former, he was quite appealing as a she.”

Keith smiled, but he didn’t laugh at me. “You don’t have to answer this, but … no, forget it.”

“Go on, what’s on your mind?”

“I can’t ask you, Eddie; it’s too embarrassing, even for me.”

“There are only the two of us here, and remember, I’m already keeping a big secret for you. Go on, what did you want to ask?”

“When you said that Dennis was appealing as a schoolgirl … this is an awful thing—”

“Come on, out with it, and I promise I’ll answer honestly.”

He looked away for a moment and turned to face me, his face beaming red. “Did you get … fucking hell this is difficult … did you get, you know, aroused?”

“You want to know if I got a hard-on when I looked at Dennis as a schoolgirl?”

He nodded, and when the question was clarified, he was finally able to look at me.

I said, “I’ll answer, but I want to know something first.”

“That sounds fair enough—what do you want to know?”

“Unless she lets you down, you’re going to be meeting what’s her name … Erika on Tuesday evening. You told me that you’d like to meet her in private, but I’d like to know if it’s just because you think it would be fun, or did you get a hard-on when you saw her at the function?”

Keith looked at his coffee and then sipped some. He inhaled deeply. “I got a raging hard-on.”

“Okay, and thank you. To answer your question, yes, I got a hard-on when I saw Dennis made to look like a girl, but obviously, I couldn’t tell him, or our friendship would be over.”

“You don’t think he’s gay or anything?”

“We discussed this before—if he were gay, he wouldn’t want to be dressed as a girl to turn a man on; he’d want to be himself, a gay man.”

“Yes, I suppose you’re right. I suppose I was wondering about Er … nothing.”

“Are you wondering if Erika is gay and maybe happy to be dressed up because she knows it’s what you’d like to see?”

“Maybe … I don’t know.”

“Do you get a hard-on when you think about being alone with Erika, even though you know what will be inside her underwear?”

Keith looked at the table for a moment and then slowly nodded before whispering, “Yeah.”

“I don’t want you to be embarrassed about this, but it sounds to me like you might be bisexual. I know it’s something you suspected about Dennis but think about it, Keith. You want to be alone with a guy who is presenting as a girl, but you’re going to be aroused.”

“Okay, I’ll be candid with you—I’m worried about the whole thing now.”

“Why? It isn’t you who’s dressed up as the sixth-former?”

“The other person will be in a sort of disguise, so I’m not going to know who it is if we meet some time outside. What if I get aroused on the evening, and it’s obvious?”

I was so pleased to hear how worried my friend might be about such a thing. “If we’re laying our cards on the table and you want complete honesty, I think she’ll be overwhelmed.”

“What do you mean, overwhelmed?”

“What better compliment could there be than dressing up as a girl and giving a good-looking bloke a hard-on?”

“Bloody hell, mate, you see this whole thing as an outsider, and it’s much clearer to you.”

“I know how much this means to you, and I want it to go well for you. I don’t know who Erika is, but I’m sure he, or she, will want it to go well, too, so you owe that much to each other. What I’m trying to say is, if you treat Erika well, if you meet each other in normal circumstances, you’ll never know.”

Keith nodded. “This is a bit like you said before; if I treat her like a real girl and let her lead the way, it will be less embarrassing for both of us and less frightening for her. How do you manage to work these things out?”

“It’s quite simple,” I said honestly. “When you first told me about how much you’d like to meet the person you’d seen as Erika, I’ve thought about it from both sides.”

“Really?”

“Yes, it was the day after the three of us enjoyed our night out when it first came to mind.” Again, this was the truth, so it was easy for me to say without hesitation. “I tried to put myself in your position, and I considered how it would feel as the guy—as you. It struck me that it might feel okay until I was in the flat alone with the attractive crossdressed guy, and how it might feel awkward for both people.”

“Wow, I was selfish. I was mainly thinking how I’d feel.”

“I considered how I’d feel if I was the dressed-up person. You know, being in a flat with a regular guy who knew my secret, that I didn’t have a pussy—I had a cock. The main worry that came to mind was that we’d enjoy a few drinks, get a bit carried away, and I’d get hurt.”

“Oh, shit, of course, you mean physically?”

“Yes, I thought about how it would be okay at first just pretending and going so far, but you know what we guys are like when our cocks get aroused. We want to have a good time, and that means shooting our load.”

“You’re bringing my worst fears out into the open, Eddie. These are the things that have been making me fret over the past day or two. Maybe I should meet Erika at the door and apologise for the whole idea. I would never intentionally hurt a girl or even a guy who looked like a girl.”

“That would hurt psychologically—imagine the effort she’ll make to look good for you.”

“I’ve really put myself in a bloody spot by trying to make a fantasy into reality.” He looked at the floor for a moment. “How would you deal with this situation?”

“I know I’ve thought about it, but that was as an outsider.”

“Please, Eddie—you seem to have thought it through better than me.”

“Okay, I’d go further than what I suggested. I’d still have the dim lights, which would be good to cover embarrassment for both of you. I’d also have a bottle of chilled wine ready, but you could test her expectations in one straightforward way.” I lifted our empty coffee mugs and went toward the kitchen but stopped and turned. “Shower and shave and get all clean, but only wear your short robe. When you answer the door, be apologetic about spending so much time getting ready, and see how she reacts. It’s worth a try.”

“Oh, my—don’t you think that would be a bit scary for … her.”

“I may be wrong, Keith, but the person who is coming to be with you for a couple of hours is probably not expecting to be chatting about sport, fast cars … or girls.”