Sam is just the cutest guy. Some might call him effeminate, but I would say he’s gentle. His soft voice, the pitch not overly deep yet still a man’s. His tall and slender body. Even though we don’t have to wear uniforms at university, his usual cotton trousers (charcoal coloured), white buttoned shirt, and navy-blue, woollen jumper could easily be a school uniform. Both his clothes and body together make him almost seem like a butler, a calm and pleasant person who would take my hand and lead me to the bedroom—um, dining room. His long, brown hair is always swept up into a neat ponytail that suits him so well. His eyes are always warm, his nose thin and a bit small, lips maybe a touch plump and yet I wonder if that’s only to tease me, looking as if swollen from a kiss that went on too long. That’s probably my imagination getting the better of me.

Anyway, that’s what I used to think before I really knew Sam.

It all started after I confessed to Sam and got turned down. I expected that. We’d only been attending college for the last couple of months and only had one class in common. Eighteen years old, I wasn’t some head-in-the-clouds romantic. I knew he knew he had a bunch of fans. But he was guarded, friendly, and always smiling, yet often alone (or was alone only to be accosted). There wasn’t really a way for me to get close to him, so I went for broke. It wasn’t like I’d lose anything if he turned me down.

Well, it still stung. I went through some friend-therapy, moping about it the evening after in group chats, then I got over it, coming to class and smiling back at him like before. Even if he wouldn’t be my boyfriend, I could still bask in his glow, just looking at him enough to nourish my soul.

Ah, those were good times.

That weekend, or maybe the weekend after—this was a long time ago now—I was going to spend the day at a nearby town. Shopping, McDonald’s—a bit of a treat. So I waited for the bus near my home and hopped on, swiped my bus card, finding a seat towards the back. A short trip later, I hopped off in the centre of town.

And I saw a stranger that looked awfully familiar. She was a girl—a young woman. Tall, slim. Brunette, her hair fell in loose curls over her shoulders. Maybe a model. But she felt more familiar than that, and my gaze must have attracted her attention because she looked back at me.

Those lips!

“She” smiled politely as I walked over. “Sam?” I asked.

“I think you’re mistaken.”

Except, that was definitely Sam’s voice, only a bit higher. “No, no, you’re definitely Sam. What are you doing dressed like that?”

“She” giggled, covering her mouth like a real lady. “Oh my. Since you’ve seen me like this, I suppose I need to silence you now.”

“W-what?” I asked, taking a step back.

The pretence gone, he drew closer to me, his eyes growing to fill my vision, and I felt every word as his breath tickled my lips. “You asked me out, didn’t you? I guess I’ll change my answer.”

“What?” I exclaimed.

Somehow, that was more shocking than being told I needed to be silenced.

“If you’re my girlfriend, there’s no way you could tell everyone about this, right?” he said, his gentle smile sickly sweet.

It didn’t take me long to understand what he was saying, but it took me a minute to accept it. In that time, he’d already taken me by the hand and tugged me over to the first shop—a shoe shop. Well, I couldn’t say he was half-hearted about cross-dressing. He knew all the different types of shoes and gushed over ones he liked and picked out some to try on. His feet looked almost delicate, still larger than most girls and yet they had a nice shape, and I noticed then how smooth his legs were, maybe even waxed. As if all that wasn’t enough, he’d even painted his toenails a pale blue to match his dress.

Oh, his outfit. I have a picture of it since he took a selfie of us together at the end of the “date”. So he wore a dress down to his knees, tied at the waist with a white belt; on top, a cream coloured cardigan. His pumps and handbag matched his dress. It was a bit light for winter, but I remember his hand feeling warm, so I guess he was fine. I didn’t notice at the time, but he even had makeup on, softening the features of his face and drawing attention to his lips—no wonder I noticed them.

Back to the story, it was fine while he was just having fun, but then he showed he really was a pervert. That is, I’m not just calling him a pervert because of the cross-dressing. Once he’d finished trying on his shoes, he turned to me and, well….

“These’ll look so good on you,” he said, slipping off one of my shoes before I realised what was happening.

I pulled back my foot, embarrassed, the chill I felt not entirely from my foot being exposed to the cold air—I was wearing stockings. “W-what are you doing?” I loudly whispered.

He giggled, looking and sounding far cuter than he had any right to. It was almost painful as I felt like I had somehow lost to him as a woman, you know? If we were stood next to each other while a bunch of contestants had to say which of us was secretly a man, he seriously would have won.

“You’re too slow, so I’ll help. That’s fine, right?” he said like it was entirely natural.

“I’ll do it myself!”

He offered me the shoe and a smile, and I naively fell for it. No sooner had I taken the shoe than he groped my foot, his grip firm, thumbs pressing into the sole. “Oh no, you’re really not looking after your feet. Don’t you massage them in the bath?”

“I shower,” I replied automatically, and then I caught up. “Hey! Let go already.”

As sternly as I had tried to say that, his touch was ticklish, my words having the strength of a feather. He didn’t let up, going about his “massage” and working all the way up to my ankles.

“You want me to stop?” he asked.

“Yes,” I whispered, glancing at the people around us who were almost interested enough to see what the commotion was.

He sighed, his dejected expression far too adorable. “Fine.”

Just like that he stopped. I let out a relieved breath, and then I realised, well, I hadn’t hated it, exactly. It kind of surprised me, and he hadn’t asked first, so of course I wanted him to stop. Even if we were “dating”, he wasn’t allowed to touch me however he wanted to. I needed to make sure he knew.

“You have to ask before you do something like that,” I told him.

“I do? Even though we’re both girls out shopping together?” he asked.

Pouting at him, I looked for the words to explain it. “Everyone has their boundaries, okay? And we’re not close yet. It’s, like, I’m not gonna pick out underwear with someone I barely know.”

I was going to regret saying that, but not for a while.

“So if we hang out more, then I can massage your feet?”

“No! You, you pervert, stop thinking about my feet,” I said, only getting more flustered after everything he said.

As if he didn’t hear, I saw his gaze fall on my other foot. At first, I glared at him, but my resolve only became weaker with time, his pitiful look a more powerful weapon than any man should have—especially a pervert.

Well, I didn’t hate it.

“Just this once,” I muttered. Immediately, his sadness was swept away by a natural smile, my shoe seemingly falling off just from that. “Because you’ve already done the other one, to balance it out,” I mumbled, more to convince myself now I’d seen his reaction that clearly showed he was taking advantage of me.

But it did feel good since I had properly consented to it.

Lost to the massage for a long few seconds, I then suddenly remembered we weren’t alone, and we were certainly the target of many glances. Putting my pathetic acting skills to the test, I awkwardly smiled and said, “Ah, thanks, my foot cramp is feeling much better.”

While I was feeling pleased with myself for such quick thinking, he kissed my foot.

He kissed my foot!

Without thinking, I slapped the top of his head. It wasn’t as hard as I could, but it wasn’t exactly light, making a very audible thump-ish sound. And then he sniffled.

“I’m sorry, I’m sorry,” I whispered, stroking the spot I’d hit. “You surprised me so I just—wait a second, why did you kiss my foot?”

Remembering what had happened first, I turned it about on him. He had the decency to look contrite, but I knew he hadn’t learnt his lesson—definitely a pervert through and through.

The rest of the shop visit went without any other issues. Maybe as an apology, he bought the pair of shoes he picked out for me, which were honestly cute. Next, he took us to a coffee shop and treated me to lunch.

It was strange. I had to keep reminding myself he was a man, constantly falling for his pretty looks and girly voice. How he held himself, how he smiled, how he drank—it all seemed so authentic. Dressing up as a girl was something that he could have done with help. That acting, though, was something learned, practised.

Such a ferocious enemy, I had to keep up my guard in case he made an outrageous request. My poor foot hadn’t recovered from that kiss, even though there had been my stockings in the way.

In the end, nothing else happened, really. He just chatted with me like we were two girl friends and took a selfie of us together, and then we said our goodbyes—he didn’t go for a kiss on the cheek, or a hug. Troublesome thoughts followed me all the way home and, by the next morning, I was ready to chalk it all up as a dream if not for him sending me the selfie from his number.

Still, I eventually thought that that was it. I wasn’t going to gossip about his “hobby” anyway, so I was ready to lock up that memory in the back of my head.

Yet, even if I thought that, I didn’t delete the picture he’d sent. He really did make a cute girl, and I normally would have hated being put beside such a cute girl when I was only at like sixty per cent power. Ah, but he looked more like a young woman. I was still self-conscious about that, always thinking I looked childish in pictures even when trying to dress maturely. That was another reason to delete it, but I still didn’t.

Well, I wouldn’t know why for a long time, so I won’t say any more for now.

Back at college on Monday, the schedules meant I didn’t often get to see people who weren’t taking the same classes as me. Sam and I only had one in common and that wasn’t until Wednesday, so I didn’t think I’d run into him until then.

Of course, I was wrong.

Sitting in the SU lounge, I was re-reading the printout in the free hour I had between lessons, making sure the piece was fresh in my mind even after reading it the night before. I’d made it to this point in my education through hard work rather than natural talent; though, my friends often said that working hard was my talent. Think whatever you want, I was still an average student who only hoped to get through university.

With my focus on reading, I paid no attention to my surroundings. That was fatal.

“Ah, I didn’t know you’d be here,” Sam said, sitting right next to me and looping his arm around my shoulder.

I froze.

“Can you send me a copy of your timetable and I’ll send you mine? That way, we can meet up when we’re both free, right?”

Slowly turning to the side, I faced him and his brilliant smile. It nearly blinded me. Unable to put a thought together, I simply said, “Okay?”

He squeezed me, like a side-by-side hug sorta thing. “Oh, I’m not interrupting your studying, am I? I like that diligent part of you.”

I half-heartedly smiled at him, almost begging him to please start making some sense.

As if to spite me, he leant in, and my heart traitorously beat fast with excitement, utterly convinced he would kiss me. But he only rested his forehead against mine, his skin cold from the outside. “We shouldn’t, not in front of everyone,” he whispered, yet it was the kind of whisper that everyone heard.

And my heart basically exploded right then as I realised he was doing this in front of at least ten other people, maybe twenty (I hadn’t been keeping track of everyone coming and going). Some of them might have even known me, waiting here for the class. His face so close to mine, the people no doubt staring at us—they both compounded together and crushed my embarrassment into a high-pitched, “Ah?”

He enjoyed that sound of anguish far too much, his eyes glittering and smile smirkful.

The hurricane he was, he moved back and gently picked up my hand, holding it as he said his goodbye, and then left. That utter prat, perverted feet molester (well, foot molester), no-good coward actually just ran off after making such a scene.

For the rest of the day and the next couple of days, my life was one, “Oh my god/gosh!” after another as my friends sought me out, sent me messages, somehow the rumour spreading. I was pretty moderate with my social media use, but I had to stay up late to finish the overlapping conversations that followed the usual, “I thought he turned you down?” to, “How far have you two gone?” and all the steps between. With no help coming from him, I made up a story about us meeting in town and having a chat and things just clicking.

Then Sam and I kinda started dating. We’d hang out on campus, eating lunch together, and maybe went to a coffee shop after school. But it was strange. I’d dated a couple of boys before, so I knew what dating meant. My old school, it wasn’t a sheltered school made up of posh kids who blushed at holding hands, but we didn’t have pregnancy scares. Well, only a few I heard of in the seven years I was there. Anyway, dating meant snogging, maybe a bit of heavy petting as you got older. My first boyfriend was in year eight, not long after I turned thirteen, and I didn’t let him get any further than a bit of groping; year eleven, I got together with another boy for most of the year, but I didn’t like how he tried to pressure me and broke things off. I wasn’t some game, grinding love points until I spread my legs.

That kind of dating wasn’t what I did with Sam. He was a bit clingy at college, sitting right next to me, but we hadn’t even kissed. Since that first day (on campus, not in town), he hadn’t even come close to kissing me.

Honestly, it started to piss me off. How can he say I’m his girlfriend if he won’t even kiss me, you know? I knew that, to him, this was just to protect his secret. Mutually assured destruction. But I also felt he was playing, having fun teasing me. And I thought he probably would have stopped pretending we were dating if I asked him to. It was just that, I didn’t hate it—spending time with him. I’d liked him enough to ask him out and he hadn’t exactly changed who he was. So, even if it was pretend, I didn’t hate it.

Maybe stranger, I didn’t hate going out with him on weekends when he cross-dressed. I’d hung out with boys before, part of a mixed group, and it had been fun having them around with their different humour. Boys liked to joke more, make fun of each other, and they’d go from acting gay one minute to discussing their favourite (female) pornstar the next. The sorts of things girls couldn’t do. But, again, Sam didn’t act like that. When we went out, it was just like going with a girl friend. We’d look in a clothing store or at jewellery, and have a small meal at a café or coffee shop, and he loved listening to my “gossip”, even if it was only me telling him about my friends and nothing really gossipy.

I didn’t really know what I felt at that time. In hindsight, I think “comfortable” is the right word. He was someone who I felt comfortable being around.

But, at that time, not knowing my own feelings, not knowing where I stood with him, it made me uncomfortable, frustrated. A month after we started “dating”, I vented out my frustration when we were sitting together in the afternoon, just the two of us in a quiet part of the campus. Though it was cold, he had draped his coat over us like a blanket—our hands kept on top and in sight in case anyone spotted us. That said, we still held hands.

Never one for subtlety, I asked him, “Why haven’t you kissed me?”

“Do you want me to?”

He said that lightly and I could see his playful smile in my mind before I looked over at him. His cheeks had some colour to them, but I thought it was probably due to the cold; I’d never seen him blush. I didn’t mind his teasing, yet it made some conversations a lot more complicated than they needed to be.

“Do you not want to?” I asked him.

“Well, I’m not disgusted by the thought of it.”

I felt my anger bubble, pouting childishly at him while I came up with a suitably childish reply. “If you won’t kiss me, then I’ll break up with you.”

He didn’t tell me off for being unreasonable. No hesitation, he leant in, reducing the distance between us to nearly nothing… and no further, his lips a breath away from mine. I’d already closed my eyes, only to open them when nothing happened. His eyes were closed, eyelashes enviously long, and I was sure he was laughing at me inside. It was like he called my bluff, saying he wouldn’t kiss me, but that I could kiss him if I really wanted to.

Well, I did.

His lips were soft. My old boyfriends, they sometimes had chapped lips, but even when not their lips had this roughness I only now realised. He had such smooth lips despite the cold, the faint taste of lip balm. Far from a snog, it was more of a caress, a warm touch between us as we gently felt each other. A second, maybe, and then he pulled back his lips, sort of lowering his head so our foreheads were touching. His breath tickled my lips.

“How was that?” he asked, a breathy whisper.

I couldn’t have said. Before, kissing was like brute-forced affection, erotic because of the squelching sounds and our tongues wrestling. Where as, that kiss had been like a promise. A promise that more kisses would come later, a promise for deeper kisses, a promise that this was only the beginning of something much greater. But how could I have said something like that to a boy—to a man? That would’ve been begging him to eat me up.

So I kissed him again instead, trying to be a sheep in wolf’s clothing. Another short kiss, but it ended on my terms this time, turning away from him.

With my lips out of reach, he brought his mouth to my ear. “Can I kiss you whenever I want?” he asked, his breath hot on my cold skin.

“Well, not if there’s people around,” I mumbled.

He softly laughed, and I felt it against my cheek. “So if we’re alone it’s okay?”

“Yes. In moderation,” I said, adding that last bit for my own safety. “And that’s enough for now.”

I managed to pull myself away from him, enough to turn and look at his face. His eyes told me I’d made the right decision to stop there, that gaze of his hungry, my heart beating faster just from the pressure.

But I didn’t hate that. Rather than “pressure”, it was like space, his way of telling me I could take another step if I wanted to. Rather than pushing, waiting for me to offer him my hand.

For the rest of the week, he was more affectionate with me—earning me the ire of my single friends when he ever so nonchalantly kissed my cheek in front of them. Other than that, his hugs when we met up and said goodbye were that little tighter, really feeling squeezed, but he didn’t feel me up while he did or anything. And he acted spoiled, practically sitting on my lap we were so close together, and he slouched against me, treating me like a pillow. And he touched me more, brushed the hair out my eyes, or just felt my cheek (and then told me I’m cold, like I hadn’t come in from the icy rain).

Not for the first time, I thought it was strange. I was happy that I’d made sure we weren’t only pretending to date. But it didn’t feel like my other relationships. I knew not all relationships were the same, but I guess, back then, I couldn’t help but compare them.

Anyway, I didn’t mind how things had changed. I liked him. I liked kissing him, hugging him, feeling his gentle touch on my cheek. It felt good in a way I couldn’t put into words, simply wanting to. Like I preferred my shower on “7”, I preferred having him around to not having him around. There wasn’t any other way for me to describe it, but, as I’ve said, I would now call it comfortable.

However, I didn’t realise what I’d set myself up for until the weekend. As we often did, I met up with him while he was cross-dressing, and we went around the nearby town that actually had shops college girls would like. Unfortunately, I didn’t feel great and he picked up on that without saying a word, cutting short the shopping and bringing me to a café.

“Sorry, I just need to…” I said, trailing off as I weakly waved my hand towards the bathroom.

Of all the things I expected him to say, “Me too, let’s go together,” was not one of them. He was supposed to say, “I’ll get us a table,” or just, “Sure.”

As if I could have a straightforward boyfriend.

The implications of what he said hit me one after another. He was certainly dressed convincingly enough to walk into a ladies bathroom without causing a fuss, and I couldn’t say anything even though he was definitely a man. It wasn’t like I thought he would do anything, his pervertedness limited to feet as far as I knew, but he was definitely a man. I also just really didn’t want to have him sitting in the stall next to me, hearing whatever sounds came out, since he was my boyfriend and I wanted to uphold a certain image of myself in his head.

No matter what thoughts I had, his sweet smile told me it didn’t matter. Though I thought that, I did also think that, if I asked him not to, he wouldn’t follow me in. But that felt petty. After all, if he really wanted to listen to me pee, then fine—he was probably just teasing me and I’d call his bluff.

He followed me into the small bathroom, four stalls and a sink and those vending machines every bathroom had. Fortunately, no one else was in there, so I just hid in the first stall (after checking there was toilet paper and that the seat was clean) before I got too embarrassed from overthinking things. I heard the door of the stall next to mine open, and I saw his feet through the small gap.

Really, it had to be on a heavy day as well. Feeling too ugh to deal with worrying about him, I just did what I needed to do, and then washed my hands. Between washing and drying, I ended up listening to him as he went and was surprised at how similar it sounded.

I waited for him, not wanting to go out there by myself, watched him delicately wash his hands. As usual, his nail polish matched his outfit. When he was dried up as well, I went to leave, only for his hand to stop me, holding mine.

“We’re alone now, right?” he quietly asked.

I froze at those thoroughly unexpected words. We’d always just been like friends when he cross-dressed, nothing more intimate than holdings hands (as he pulled me to the next shop).

But that wasn’t what had stopped me. “It’s gross here, and I feel yuck, and what if someone comes in,” I half-heartedly grumbled. Of all the excuses I said or thought, “You’re cross-dressing,” wasn’t one of them.

And as if he could tell, he silenced me with a kiss.

No matter what he looked like, those were his lips, soft—no, sweeter. I wasn’t the only one with lip gloss on. With my eyes closed, I could have pictured him like he normally looked: a smartly-dressed man. I could have, yet I didn’t, his long eyelashes, eyeshadow, red lips what lingered on my mind’s eye.

The heat, the need, this was the kiss our first kiss had promised. He didn’t nibble on my lip, or slide his tongue into my mouth, or try anything. An innocent—almost childish—kiss like usual, except that he stepped up to me, his arms wrapping me in a tender embrace, the warmth of his lips and his body a comfort I’d never felt before. As unpleasant as it sounds on paper, it was like he kissed me with his entire body. All my worry left, swept away, and I could have stayed like that forever.

Then the door creaked, and we were apart in an instant. The prat, he didn’t so much as blush, meanwhile I felt like my cheeks were on fire, even my ears hot. So I was the one given strange looks as we went back to the café. Maybe it was obvious to them what had happened, but I didn’t hear anyone say anything. That was all I needed—my friends accusing me of cheating on my boyfriend with a woman. It would have been quite the scandal. I hoped we were old enough that the scandal was the affair, though, rather than me being gay. I didn’t personally know any lesbians at the college, but a few of the guys were “out” and, as far as I knew, they weren’t treated badly for it.

Anyway, he didn’t kiss me again that day. The more I thought about it, the more I decided he had just wanted to distract me from whatever my problem was. If he’d really wanted to tease me, he would’ve made me kiss him, I thought.

The next week passed as nicely as it could, him back to dressing as a man and acting boyfriendly with me, and I foolishly thought that, maybe, I had got used to his teasing.

Too foolish.

We met up at the weekend, him back in a dress, and he took me to a lingerie store. Lingerie. I was already embarrassed when going there with my friends who were actual girls, pre-emptively a little embarrassed for when they’d find something skimpy and hold it up, asking if it would like good on them and forcing a flickering image in my head of just that. Swimming classes had been bad enough, and P.E. wasn’t much better, and I was thoroughly glad when that was over and done with in sixth form. We weren’t all comfortable with our bodies.

Sam clearly was too comfortable, though. “We should get something for Christmas,” he said, like it was perfectly normal for girl friends to buy each other lingerie, or for a girlfriend to buy her boyfriend lingerie.

While I walked around with warm cheeks, he glided here and there, picking up and looking over whatever took his fancy. He held up chemises and babydolls against himself and asked me what I thought, and, somehow worse, he held other ones up to me, looking me up and down before shaking his head.

I wanted to shout at him, “I’m sorry I don’t look as sexy as you, okay?”

After we moved on from the sheer slips of nightwear, it didn’t exactly get any better, thongs and garter belts and lace bras. Seeing him linger on a pair of crotchless knickers helped exactly negative a lot. At the very least, he only peered at the section of dildos and vibrators and who-knew-what-else. It was bad enough my friends saying they were going to get me something from there for my birthday. That wasn’t to say I wasn’t interested, just that I very much wanted no one to know about what went on between me and myself.

High on the relief that he wouldn’t be taking me to that part of the store, I was blindsided when he asked, “So, what’s your size?” while holding up a cute bra.

It was like I needed to blush and pale at the same time, hot and cold. “No way,” I managed to say.

“If you don’t know, we’ll get someone to measure,” he said, turning to look for a shop assistant.

Unable to speak, I just grabbed his arm, trying to convey, “Please don’t,” with my tight grip.

Smiling sweetly, he leant in—showing me his ear. I was tempted to hurt him, really tempted. Gathering my courage, I feebly mumbled one of my most precious secrets.

He hummed to himself, going back to the rack and flicking through until he found one he liked. Then he held it out to me. “Let’s go try it on,” he said.

“What?” I blurted out.

Softly laughing, he nudged my shoulder around so I faced the changing rooms, and then nudged my back the whole way there, while my mind was left behind on the floor where we were. By the time I pulled myself together, I was in front of the curtain and clutching the bra tightly for support. (It provided me a more emotional support than the usual physical kind.)

When I turned around to glare at him, all he said was, “It’s important that it fits properly, right?”

It didn’t look like he would give up easily, so I stepped inside. I thought then that I could just pretend to try it on.

“I can’t hear anything.”

I seriously considered if he could read minds. After a deep breath, I decided that it wasn’t like he would peek, probably, and it was a cute bra. With how expensive bras were and since I wasn’t sure if I’d finished growing, I hadn’t bought more bras than I needed. So I thought that this bra would make a good present for myself. That he had picked it out didn’t matter.

Knowing that something was more likely to happen if I took too long, I quickly took off my top and undid my bra. With the new bra on, I was leaning forward to finish the fit when he asked, “How is it?” I nearly fell over, suddenly hearing him giving me such a fright.

Before he got the stupid idea to check on me, I said, “Fine!”

“Really? Can I see?”

“No!”

I covered my boobs, glaring at the curtain in case he could see through it somehow. Maybe he had x-ray vision to go with his mind-reading power. When nothing happened for a few seconds, I calmed down and went back to the bra, tucking myself in properly and all that.

Then I looked at myself in the mirror. It really was a cute bra.

Once I’d admired it enough, I changed back to my bra and put my shirt back on, carrying my coat over my shoulder. Opening the curtain, he was right there and gave me a knowing smile.

“What d’you think? It suits you, right?” he asked.

I didn’t know about that, but I liked it and said as much.

“Then we’ll have to get something to go with it,” he said, taking the bra off of me and putting it in a basket (which he must have got while I was changing) alongside a matching pair of knickers. Well, I say knickers, they were a thong, but not a g-string, some fabric there to cover the bum and front and it was a few centimetres wide at its thinnest. However, the fabric itself didn’t exactly cover up what it covered, noticeably translucent except where the flowery pattern was.

Rather than face that reality, I focused on the other bra in the basket. It was bigger than mine, and I thought it was probably for him, and then I had to run that thought past my common sense. It was something I’d not thought about before, but he did look like he had breasts. They were fairly big, but that was balanced out by his height, so they looked an average size on him. I guessed that was what he was going for, too flat or too big noticeable. The sort of boobs that were there but not the sort of boobs that would be thought about.

While I’d been distracting myself with that train of thought, he’d led us to the tills. A lady was behind the counter, and she chatted away with him as she rang everything up, the total coming up rather high. Lingerie wasn’t cheap. He paid without any sign of reluctance or regret, cash. I guessed he didn’t want to pay with a card that started with “MR”.

“You two must be close, shopping together like this,” the lady said with a smile. “Me, I fought with my sister until we were in our twenties.”

It took me a second to understand what she was saying, about to say we weren’t sisters, but he just had to open his big mouth first.

“Oh I just love my little sister so much, I have to spoil her,” he said.

And the bit I got stuck on wasn’t him calling me his sister, but him saying he loved me. I never found the courage to ask him if he meant it at that time.

Though I offered to repay him for my stuff, he just told me it was his Christmas present to me; when I offered to pay for his stuff, he told me he wanted something I picked out myself. Unsurprisingly, I wasn’t exactly keen to buy my boyfriend women’s lingerie. I ended up paying for lunch instead, and bought him a tie the next weekend (because I didn’t know what to buy a boyfriend without being told and it seemed like a good idea at the time).

That was the start of me becoming strange, or maybe it’s better to say stranger. I’m sure you already think I’m strange. In my opinion, this was all still in the range of, well, not normal, but tolerance. It was a strange “hobby” for him, but I knew about it from the start and it wasn’t like he dressed up to trick men or spy on women or anything, ultimately harmless (for everyone except me).

I didn’t really consider that he might have been transgender, in part because he didn’t tell me to treat him as a woman, and in part because I guess I didn’t want to. It would have been a really hard conversation to have and so I naturally avoided it—because that’s what teenagers do.

Me becoming strange, though, was all to do with me. He let me take home my present that day. I was glad, not particularly wanting to open it in front of my parents at Christmas. That night, when I wore it, I really liked how it looked on me. He had a good eye. But when I thought of who gave it to me, I thought of “her”. The image in my head was him cross-dressing. Normally, I always thought of him as him, dressed and looking like a man.

Over the next week, there were times when we kissed and I remembered that kiss we had in the bathroom at the café. That kiss had been special. I wasn’t sure if it was because of how terrible I felt at the time, or the thrill of kissing in a public place, or how he’d held me so closely.

It didn’t occur to me that him cross-dressing could have had anything to do with it.

There were also times when I remembered him saying he “loved” me, and he’d also said that while cross-dressing, so that was how I thought of him when I remembered it. I started to realise that I really did feel differently with him than with my last boyfriends. The lady had mistaken us for sisters and, really, the more I thought about it, the more I felt it wasn’t entirely wrong. I don’t have a sister, but I’d imagined what it would be like and definitely had a fairy tale image in my head (no doubt far different from what reality would be). With Sam, it was kind of like that fairy tale. Someone even closer than a best friend and we just happened to sometimes kiss.

That was when I started to understand that, in a way, he was my comfort. My home away from home. I’d always thought boyfriends were like coffee machines. A coffee machine made coffee when I asked for it, and boyfriends made “horniness”, giving me that warm feeling. But I didn’t want the coffee machine after I’d drunk the coffee. Not that I drank coffee. With Sam, I wanted my cake even after I’d eaten it. (Sorry for mixing metaphors.)

Terrible and rambling analogies aside, I’d started to lose the distinction between him when he was and wasn’t cross-dressing. I didn’t think of him as a guy who sometimes cross-dressed, I thought of him as him even when he was cross-dressing. In the Christmas break, we met up a few times and, since it wasn’t college, he was cross-dressing, and I still happily took his hand, walked closely with him. There were a few times we were alone and I gave him a quick kiss. I didn’t know if that surprised him. If it did, he didn’t say.

When term started up again and I saw him dressing as a man, it was a little strange like a part of me expected him to turn up in a dress. (Not that he always wore dresses, sometimes skirts or tight-fitting jeans with cute shirts and blouses.) I didn’t understand it at the time, but I also felt his unspoken discomfort, noticing it—especially his kisses. When we kissed, he was more reserved than when he was cross-dressing, a little tense.

It wasn’t a big deal or anything, but it became more and more noticeable the more time I spent with him. Maybe it had always been like that and I only noticed now we were closer. I wanted to ask him about it and yet was too scared, afraid it was something I shouldn’t mention.

After all, as close as I felt with him, it was a feeling, not a fact. There were a lot of things I didn’t know about him and that included why he cross-dressed. He’d never said, I’d never asked.

So I asked him.

Probably my only redeeming quality as the “heroine” of this story is that I don’t stew in my thoughts when something bothers me.

It was when we were out together, so naturally he was cross-dressing. Rather than give me an answer on the spot, he invited me to his flat, saying it was best to talk there. I was fairly curious about his house and room and stuff already, so that was a double-win for me. As for being alone with a man, it didn’t worry me since he’d always respected the boundaries I’d drawn. Sometimes he respected them from very close, but respected them nonetheless.

It was a normal enough flat from the outside and on the inside. He lived alone, he told me. There were a couple of pictures here and there—family photographs. His parents were tall like him, and he had a sister who could have been his twin when he was cross-dressing, and I thought she was probably the source of his extensive girly knowledge.

It actually had surprised me seeing her at first, thinking he had pictures up of himself cross-dressing, but then there was a photo of both siblings together: one boy and one girl. As he led me to his room, a little excitement bubbled up, glad to be taking a big step together. At the same time, I felt a knot of dread in my stomach because he’d never mentioned having a sister before. It was the sort of thing that surely would’ve come up in the two-and-a-half months we’d been dating.

His room was definitely a girl’s room. There wasn’t any other explanation. I wanted to jokingly ask him if his sister decorated it for him, but I fortunately couldn’t get the words out.

Once he’d made sure I was comfortable—sitting on his bed, leaning against the wall with a pillow to soften it, while he sat at his desk—he just destroyed me with a single line. “My twin brother killed himself.”

I was sobbing within a second of hearing those words, the most ugly sobs imaginable. If he had laughed and said it was just a joke, I would’ve slapped him so hard, even though I wanted him to do just that. Because, if those words were true, he was hurting far more than I could ever hurt him. I could see that in how he held himself, how weak he looked in that moment. Fragile. I wanted to hug him to death, but I worried just touching him would break him.

“He was… bullied, because he was born a girl. He acted boyish and then started to dress like a boy. He was called disgusting, freak, they’d trip him up, push him over. If any boy talked to him, everyone else would start calling them gay. If he bumped into a girl, they’d scream as if he groped her. Dyke, tranny, faggot—any slur would do.”

It had been too much before, but, hearing all that, my heart actually ached. And it wasn’t just what he said that hurt. Seeing him so blank, as if he was talking in his sleep, or reading aloud something really boring. I wanted to ask him to stop so I could recover, but I couldn’t do that to him. I couldn’t ask him to close up right after opening up.

“I… started cross-dressing because I wanted to know how he felt. Even as I saw it all happen, even as I talked with him and tried to comfort him, I knew I couldn’t possibly understand how painful it was. So I wanted people to say the same things to me, just to feel some of the pain he did.”

He choked on his words there, taking a moment to dry his eyes and clear his throat.

“But the only person who knows is you, and you’ve only been kind to me,” he softly said. “And I’m too afraid to come out, afraid I’ll end up like him.”

I didn’t know what to say. It was too much for me to handle. But I slowly thought, and I slipped off the bed to walk over and hug him. He cried, more than I’d ever cried in my life, and I cried with him. It must’ve gone on for at least ten minutes, my legs sore and eyes puffy when we finally stopped.

“You’re, um, seeing a therapist, right?” I quietly asked, still hugging him.

“Yeah. She’s helped a lot.”

That took a lot of the weight off of me, and I was really glad to know someone who knew what she was doing was helping him. So I felt comfortable enough to say, “I think… it’s important to be who you are, but I also think you should do it for the right reasons. Otherwise, won’t it just be painful?”

That was my way of telling him that, if he cross-dressed, he should do it because he wanted to. I didn’t want him to hurt himself over a past he couldn’t change.

“You’d still love me if I was a woman?” he asked.

I hadn’t even used the L word before. Putting that to the side, I wasn’t entirely sure what he meant. There was a difference between cross-dressing and being a woman, so I thought he might have meant if he really did go the whole way, hormones and surgery. But then I felt he wasn’t really asking that. He would have said if he meant it so seriously. Rather, it was about whether I’d still love him if he wasn’t a man.

And, that answer was easy. I had already stopped really seeing him as a “gender”. Sam was Sam. Besides, I’d known both sides of him since the start of our relationship. However he looked, however he wanted to call himself, Sam would always be Sam to me.

“Yes,” I said, and I followed my reply with a kiss. Not an innocent one. I wrapped one arm behind him, the other hand settling in his hair, and I pressed down on him with the height difference I had standing while he was sitting.

I needed that comfort. Hungry, I tasted his lips, stoking the fire inside me. He fed me, fanned the flames, his hands settling just at my waist, his nails pressing into my side. I wore the underwear he’d bought me, almost wishing he pulled down my skirt so he’d see me in the thong. Adjusting our positions, I sat on his lap, and I slowly grinded against him, unable to keep myself still.

He couldn’t take much more of that before standing up, forcing me backwards while we still kissed, hugged. My legs hit the bed and I buckled over, lying on it, and he followed me down, sandwiching me between himself and the mattress.

Man, woman—there was only Sam to me.

Before we lost ourselves, he slowly pulled back. I chased his lips, but I couldn’t find the strength to sit up and my legs were too weak to stand. Until that moment, I’d never realised that girls literally meant it when they said stuff like, “His kiss turned my legs to jelly.”

He was blushing. With makeup on, it was hard to tell. Maybe I’d actually seen him blush a lot and just hadn’t noticed. For me, it was a very erotic sight, finally seeing the calm and collected Sam flustered—I just wished I could actually do anything.

As it was, all I could do was ask him, “Was that the right answer?”

“I love you.”

He couldn’t even let me have one little win.

The only other bit of that day I can remember, I asked him a little later, “When I’m talking to your parents, should I, um, call ‘him’ your brother?”

He smiled warmly, gently nodding. “Yeah, we all remember him that way.”

After that day, we became more intimate, but still nothing really under the clothes. Not that I would’ve said no if he asked, his touches really knew how to leave me hot and bothered. I visited his flat now and then and even met his parents—surprised that they treated his cross-dressing so normal, his mum even thanking me for being such a good friend to her “daughter”. And he visited my home (as a “friend”), my mum apologising for her daughter being stubborn and moody but good at heart. He enjoyed hearing that. At university, I stayed in dorms, so I preferred going to his place, more private there.

In the back of my head, I started to ask myself: Is he trans? I didn’t really know much about it. Even when I looked online, it was hard to tell where fact and opinion ended, or how relevant other people’s personal anecdotes were. My feelings were that he was more comfortable dressing as a woman, that he seemed happier.

It was especially noticeable when we were kissing and stuff like that. Before, I’d thought it was just that we were in public. But if I went out with him straight after class, even if we went to his flat, he just didn’t seem as comfortable touching me, always wanted to get “dressed up” first.

The more I felt he wanted to be a woman, the more I thought about what that meant for me. I wasn’t overly worried about being a “lesbian”. Maybe some people would care, but I didn’t think my friends would hate me for it, and I felt my family would be okay with it. Not happy, but okay. (At the least, my mum liked him, so that would maybe help.)

And sex, well, I’d read and heard that most women didn’t orgasm from it anyway, so I’d still have to finish myself off even if he did have surgery down there. Otherwise, foreplay and stuff didn’t actually change. He still had fingers and a tongue and there were dildos and whatever.

In the end, I didn’t really find or think anything that worried me. Well, that’s not strictly true. There were worrying statistics about suicide rates post operation that I had to really research before I realised why they were “wrong”, and there were still horror stories about botched surgeries—and some images to go with them, which I clicked on out of stupid curiosity. Things like that. I didn’t worry about us, though. I very much felt that I loved Sam and that had always included all sides of him.

My thoughts started to become months and years away rather than days and weeks. I wondered what sort of job he wanted, where he wanted to live, a garden, pets. Children, well, I wondered what he’d looked like as a child, but there were only pictures of him and his brother when they were teenagers around his flat. I wasn’t brave enough to ask to see childhood pictures since he might ask to see mine.

I loved him, you know? I loved Sam.

It was my birthday when the next “event” happened, the last one for this story.

February fourteenth, happens to be Valentine’s Day, so he obviously wanted to take me to a lingerie store. It was less embarrassing for me compared to before, those worries I’d had entirely forgotten. We’d been to the women’s sections of other clothing shops a handful of times, so I really was desensitised to it.

As always, he had a much better eye for this sort of stuff than me, picking out a few things for me to try on. A push-up bra, two nighties. He kept the knickers (that went with the bra) and a pair of stockings in the basket. I wanted it all, happy with the fit and the look.

And then I looked for something for him. I’d learnt his “sizes” from seeing what he bought, so I didn’t have to ask him, just said I wanted to look around some more. It was strange. I’d picked out a couple shirts and blouses for him, but I didn’t have a good feel for what really suited him. Our bodies were completely different shapes, tall and slim versus normal and… normal. He was cool and mature and I wasn’t.

Still, I wanted to do it. I thought that maybe we hadn’t gone further because he was worried or ashamed or something else about his body—underneath the clothes and makeup.

A bright red bra and matching knickers, that was what I chose. Lacy and sexy and the sort of thing that I thought would suit his image. When I put them in the basket, I just stood next to him, looking at nothing in particular, and said, “I’d like to see you in them one day.”

He didn’t say anything back to me. When we went up to pay, he let me buy them and he bought the rest for me. I evened it up a bit by paying for lunch.

Then he asked me if I wanted to come to his place.

He led me to his room, as girly as ever, and asked me to wait there while he changed; he took the bag of things we’d just bought with him.

My heart beat faster and faster in my chest. More than just seeing him nearly naked, I knew things wouldn’t end there. My own thoughts did as good a job as kissing him would have, my dirty mind overflowing with all sorts of things I’d been “researching” over the last few months. When I was reading diaries and stuff written by transwomen, or people dating transwomen, I wasn’t going to skip the intimate parts, was I?

So when he opened the door, I was practically squirming, flushed, full of anticipation. He only wore a bathrobe. I felt myself ache, this waiting almost painful.

As he let go of the bathrobe, all he said was, “I’m sorry for lying.”

Hiding beneath that bulky cloth was a very soft body, smooth and flawless. And it was a woman’s body. The boobs, in the bra I’d picked out, weren’t just pads. The knickers were fairly sheer, not enough to see through, but there clearly wasn’t a dick there, only the slight bulge of the mons.

As things clicked into place in my head, I felt stupider by the second, and Sam kept apologising. She said things like, “It got harder to tell the truth every day”, and, “I never meant to let it go on this long”, but I couldn’t really focus on that.

My thoughts settled on relief that she wouldn’t have to get surgery, and that she was so beautiful, and glad the stuff I’d chosen fitted her. Really, I was too horny to care about anything else. Maybe, if it had been a more calm reveal, I would’ve been hurt or something. But I was just a stupid and hormonal teenager with a beautiful and sexy girlfriend in front of me and I’d spent the last few minutes thinking about how I was going to lose my virginity.

And, well, I did.

That’s the story of how me and Samantha met.