The Best Friend

I'd been underdressing ever since I snooped into my Mom's lingerie and since then I'd been obsessed with wearing women's underwear. Really, I never wore men's underwear anymore apart from if I had appointments when I thought they may need me to drop my pants. As well as women's underwear, I also had stockings, tights and bodysuits, ones for daily use and lingerie style ones for an evening. My pyjamas were always nighties or slips. I'd recently had my 19th birthday and was attending university but locally meaning I was able to stay in my local city of Newcastle in the north-east of England. Thankfully, I had a very understanding Mom. She was involved heavily in a legal company and had a well-paid job meaning that even though there was only the two of us in the house, there wasn't much pressure on me to get into work and I was able to pursue a career of my choosing. That didn't stop me having a part time job though, so I had some money to spend on myself.

My Dad wasn't around at any stage of my life which meant that I was very close to my Mom. I came out as gay to her when I had just turned 18. Something inside me just clicked one day and I just knew. She was super understanding, and it was never an issue for her. I had her down as being the best Mom ever. One day, she found out my biggest secret. I bent over in front of her one day and didn't think once about my choice of underwear for that day. My jeans slipped down and about an inch of the thong I was wearing peeked out the top.

'James, are you wearing a thong?' She asked me quickly whilst I was still bent over.

Without even looking at her, my face turned a crimson red, 'Mom...'

'Stop,' she held the palm of her hand out in front of her. 'I don't want to know why you wear them, but I don't want you to hide it.'

'Really?' I was shocked.

'Yes, I want you to be comfortable when you're at home. I don't expect to see you walking round in them and nothing else, but if you want to put things like that in when you do a wash, I'm not bothered.'

'Thanks Mom, it's not sexual, honest,' I tried to defend myself. 'I genuinely find them more comfortable and feel more comfortable.'

'I don't need to know,' she laughed.

That was the day that I got rid of most of my male underwear. And from then on, I was still a little shy about washing them when Mom was in the house, but I was more confident when it came to coming home with some new purchases. I also expanded my wardrobe to include more female clothes including skirts, leggings & crop tops. I was definitely crossing the border into 'femboy' territory. We never talked about what I was buying, we had a boundary with stuff like that and we never crossed it. I think we had an understanding relationship. Sometimes I felt bad, my Mom didn't have much of a life outside of work and having raised me on her own, she hadn't had a relationship since my Dad walked out when he found out she was pregnant.

Life for my generation growing up was difficult. The cost of living was going through the roof which meant that even if I wanted to move away for university, I wouldn't have been able to live comfortably without working full time alongside my course. Like I mentioned earlier, luckily my Mom was willing to let me stay at home whilst worked part-time to help pay my way. And my best friend was in the same position. Me and Joey had been friends since nursery and had grown up going to the same schools and colleges, and now we were both attending the same university. Joey still lived at home with his parents as well and I spent plenty of time around their house. Joey had an older sister, Chantelle, who I'd always got along with as well seen as though she was only a couple of years older than us.

They both new that I was gay. It wasn't something I hid from people anymore so if people asked me, then I would tell them. I also didn't hide the fact I wore panties daily. Obviously, I didn't go around flashing them to anybody I saw but if people did see or asked me the question, I would never deny it. In fact, both Joey and Chantelle knew of my love for lingerie. I don't remember quite how Chantelle found out, but Joey caught me as well with an accidental slip. He wasn't fazed by it either and it never affected our friendship which was a relief. I didn't have many friends, but those ones I had, I didn't want to lose because I'd known them for a long time.

In terms of sexual experiences, I didn't have a lot. I quickly realised that topping wasn't for me, and I enjoyed the one being fucked. I lost my virginity to an older guy from Grindr not long after my 18th birthday. It wasn't the greatest experience, but I enjoyed it, nevertheless. Since that initial first time, I hooked up with a couple of students during freshers week which were better experiences. And after I became more sexually active, I made sure to sign up on PrEP. I hadn't tried bareback but it was something I'd like to do in the future. The only problem that I had with meeting guys was that I always had to do the travelling as it was easier than explaining who all the strange men were to my Mom.

Although my Mom had never had relationships since my Dad, I knew she was sexually active. And I knew because I came home early one day and caught her in the act. With our house, we rarely used the front door to get in and out. Because we parked our cars on the driveway, we would often use the backdoor to get in. One day, my lecture at Uni had been cancelled early due to staff shortages, so I cycled home that day and parked my bike around the back of the house. As I walked in the back door, I immediately heard the noises coming from the living room. The sound of body slapping against body and the moans of two people who were having sex. Rather than just leaving the house though, curiosity got the better of me and I edged towards the living room before I was able to see through the glass on the door.

'Oh fuck,' I heard my Mom moan. 'Keep going, don't stop.' The sight in the living room made my cock stiffen inside my panties. Clothes were all over the floor and my Mom was riding some dude who I'd never seen before. She was naked except for a pair of stockings, her tits bouncing freely and the juices from her pussy glistening on his cock. Before either of them saw me, I managed to get back out the house and made myself scarce for a couple of hours before coming back home later but I digress from the story.

When I came out as gay to my Mom and friends, it's safe to say that none of them were shocked and everybody I met always said I gave off the 'gay vibe,' whatever that meant. But I did think I knew what they meant. It's safe to say that I was quite a feminine guy, and I know that comes as a shock to you all given that I love lacey underwear. As well as the underwear, I had shoulder length brown hair and depending on how I was feeling on the day, I would do all kinds of different things with my hair. It might be straight, curled, tied up, platted, or just simply wearing a headband but I didn't see why I should have all this hair and either have it down or in a boring ponytail. I loved to shave all my body as well, there was just something about having a smooth body that turned me on. I was only small as well, or what I considered to be small. I was just over 5ft 8, whereas a lot of my friends were well over 6ft, and Joey was at least 6ft 3. In terms of cock size, I wasn't less than impressive. A solid 3 inches when flaccid which increased to just under 6 when I was fully erect.

One day after one of our lectures, me and Joey were heading through the city centre so we could catch the metro back home. On the way through, I asked Joey if he would mind if I popped into a shop. The shop I wanted to go into was called Next, but the real reason I wanted to go in there was because they did Victoria's Secret lingerie in the store. When in the shop, I was in my element. I was looking through the different styles of panties trying to find enough to get the offer of 5 panties for £30. I could sense that Joey was uncomfortable as I looked through the different styles and holding them against my body to make sure I was getting the right size.

'Doesn't it annoy you?' He asked as he looked around, 'all these people looking at you?'

'You get used to it after a while,' I told him, holding a lace pair of panties in the air. 'Plus, sometimes I just tell them I'm shopping for a girlfriend and we're about the same size.'

'And I bet they fall for that don't they?' He laughed.

'They do... sometimes.' I grabbed the last pair of panties I wanted before walking towards the checkouts. 'But it is a bit of a giveaway when you've got a VPL or VTL depending on the trousers I'm wearing.'

I paid for my panties, and they placed them into one of those cute little Victoria Secret bags before handing them to me. 'God, if looks could kill,' Joey said as we were walking out.

'You know what the problem is,' I whispered to him as we reached the exit. 'They're just jealous that I look better in panties than they do.'

He laughed, 'are you coming back to mine for a bit?' We headed towards the metro. 'Bit of gaming, and watch TV.'

'Sounds good to me,' I told him. We quickly made our way onto the metro and were soon heading towards Joey's home. It was great that he lived so close by, when I was ready to go home, I'd only have to walk for about 5 minutes before getting home. As we approached his house, there wasn't any cars in the driveway.

'Looks like Mom and Dad must still be out,' he said as we walked towards his front door. He turned the handle and it opened, 'but obviously Chantelle is home.' We walked into the house, leaving my shoes in the hallway, and headed through the living room and towards the kitchen.

'Is that you bro?' We heard from the kitchen, and then Chantelle appeared in the doorway. 'Hi James,' she said and waved at us both before turning back into the kitchen.

We walked into the kitchen, and I placed my VS bag onto the breakfast bar, my eyes locked onto Chantelle who was reaching into one of the cupboards below the sink. She had nothing on apart from an oversized t-shirt and a pair of lace cheeky panties. I recognised the panties straight away, seen as though I'd just bought myself a pair. Chantelle was an attractive girl; she'd just turned 22 this year. She had long blonde hair, was very petite, had small tits but a big round butt from all her workouts. And she obviously wasn't shy when it came to showing off her body. She'd been seeing a guy for a few months now. He was a lot bigger than she was and he was built like a rugby player.

'For fucks sake Chantelle,' Joey said. 'Will you put some clothes on.'

Chantelle just laughed at him, 'you need to lighten up a little bit bro, what's the matter? Has it been too long since you got laid?'

'Fuck off,' Joey snapped back whilst I tried my best not to smile.

'Oooo I see somebody has been treating themselves,' Chantelle said when she noticed the bag on the counter. 'Is there a lucky someone who gets to see those?'

'No,' I blushed. 'I'm the only one who's enjoying them at the minute.'

'Well, there's someone out there for everyone,' she said laughing. 'I'm going back upstairs; Chris is up there do don't be too weird down here.'

Joey pulled a funny face as Chantelle disappeared out the kitchen and upstairs. Me and Joey then headed into his garage, which had been converted into another room and was no longer used as a garage. His parents had converted it because Joey had been stuck in the smallest room in the house. He still used it to sleep in, but the garage was now where his TV and games consoles were. They'd furnished it nicely so must've put a decent amount of money into it. Over the next hour or so, we sat and played different games whilst chatting and eating snacks. These were the days I enjoyed the most, when we could just sit and do nothing, like we had no responsibilities.

'Do you mind if I use your toilet?' I asked after drinking what felt like a full 1.5 litre bottle of Pepsi.

'Dude, why are you even asking?' Joey said laughing. 'You're in this house as much as me.'

I knew that I didn't need to ask, but I always thought it was polite to ask before doing something in someone else's home. 'Do you want anything getting on my way back?' I asked as I started to stand up from the sofa and walk towards the door.

'Just a refill on my drink if that's okay?' I turned back and grabbed his cup from the table and headed through the kitchen, leaving the cup in there before heading upstairs to the bathroom. When you reached the top of the stairs in Joey's house, the bedrooms were at the other end from the top of the stairs and the bathroom was straight in front of you. It usually meant you could get into the bathroom without anybody even realising you were upstairs.

I quickly peed and cleaned myself up before heading back out of the bathroom. As I stood at the top of the stairs, I could hear feint moans coming from further down the hallway. I went to take my first step down the stairs before I heard someone moan, 'oh fuck.' Curiosity got the better of me and I wanted to see what was going on. I tiptoed down the hallway towards Chantelle's room. The door was open a couple of inches as I got closer, and the noises got louder. The closer I got, the more I could hear skin-on-skin contact. Even though I was gay, I was something of a voyeur. Ever since I saw my Mom getting fucked in the living room, the thought of watching people having sex turned me on.

'Fuck me,' I heard as I got closer. I got as close as I could and peeked into the room. Chantelle was on top of her boyfriend and was riding his dick. Panties still on and shirt pulled up as he reached for her tits. My cock started to stiffen in my panties, and I wanted to pull it out and jerk off, but I knew I couldn't stay here for long otherwise Joey might come looking for me.

Just as I was walking away, I seen Chris flip Chantelle onto her back and immediately start fucking her again. I quickly got a glance of her petite pierced tits as they bounced up and down. The way Chris was pulling out before slamming himself back in must've meant he had a decent sized dick. 'I'm gonna cum,' I heard him moan.

'Yeah? You gonna cum for me,' Chantelle moaned back at him. 'Fill me up, please, I need it.' I heard Chris climax and quickly but quietly made my way back downstairs in case they came out to go to the bathroom. My own dick was rock hard, so I took a minute or so before filling Joey's cup up and returning to where he was.

'You alright?' Joey asked me as I got back into the room and sat down.

'Yeah, sorry. Mom phoned me as I was on my way back down,' I lied, thinking on the spot of something he would believe rather than the truth of me watching his sister getting fucked.

We continued playing games for another hour or so before his parents eventually got back from work. His Mom popped her head into where we were so she could say hello and tell Joey what time she planned to have dinner ready. She kindly offered me some as well, but I was planning on heading home before then. His Mom came back in shortly after and when she asked Joey something, he was a bit snappy in response and was quite rightly shouted at.

'Dude, are you okay?' I asked after she'd gone.

'I'm fine,' he said quickly.

'Yeah, you really seem it.' I said, pausing the game and turning to him. 'You've been off for the last few days, what's going on with you?'

He didn't respond to me, but I wasn't going to stop so I tried to make a joke of the situation, 'was Chantelle right? Do you need to get laid?'

'I mean it'd probably help,' he said and smiled for the first time since we got back to his house.

'Seriously?' I was shocked. 'It can't have been that long, surely?'

'Well, it's been me and my right hand for 6 months now,' he said in a joking sort of way. And I was shocked. I mean Joey was in the middle of a sports science degree, regularly went to the gym and had a body most athletes would kill for. Hell, if I thought he was gay, I'd be jumping all over that body trying to get his attention.

'Man, that's rough,' I told him. 'Maybe we need to go out this weekend and get you some action.'

'Nah, I've been on Tinder for months and there's been no bites,' he laughed.

'Have you ever tried Grindr?' I looked at him and smiled.

'Fuck off,' he said with a smile. I didn't push anymore and instead went back to playing games.

After another ten minutes of playing, my controller's battery died. 'Argh, fuck sake, my controller has died,' I said frustratingly as we couldn't pause an online game.

'The charging cable is under the TV cabinet,' he said not taking his eyes off the game.

I moved off the sofa and down onto my hands and knees to grab the cable. Unintentionally, I was giving him a good view of my ass if he wanted to look. 'I hope you're not staring at my ass,' I said laughing whilst looking back towards him. And I caught him looking.

His face went red. 'Well, it's hard not to notice when all I can see the bright pink waistband of your thong sticking up in the air.'

I reached back and could feel the top of my thong, 'oh shit yeah, sorry,' I laughed it off. 'I hope you didn't get a boner there; I know it's been a while for you.'

'Anything is turning me on at the minute,' he replied laughing. I plugged my controller and set it down to charge as Joey finished his game, I then joined him back on the sofa.

'You know, it's such a shame you don't have a friend who likes sucking dick,' I nudged him gently. 'One that even can look feminine, dress up and help you out.'

'What are you saying?' He looked at me nervously.

Now was my time to be brave, I was still horny after watching Chantelle getting fucked. 'Look, as a good friend, I would happily help get you off, that's all I'm saying.'

'But I'm not gay, and that would just make things weird between us,' he said defensively.

'It's not gay when the person sucking your cock looks like a girl,' I told him.

'We can't do that though, it just wouldn't work,' Joey said.

'Why wouldn't it work?' I jumped up and sat on the sofa next to him. 'Or are you just scared you'll like it too much?'

He took a deep breath, 'why are you pushing for this? It's come out of nowhere and now you'll happily suck my dick.'

'Look, we both get something out of it, you get your dick sucked and get to blow your load, and I get to suck some dick which I haven't done for a while,' I put it plainly. 'And let's be honest, you were checking out my ass earlier for far too long.'

I think I was finally getting through to him, as he looked like he was starting to relax so I kept going, 'all you have to do is sit there, head back and eyes closed and let me do the rest.'

'I swear, if we do this, it's just a one-time thing and only because I'm so horny,' he said after a moment of thinking.

'Is that a yes then?' I asked him.

He looked at me and repeated once again, 'just a one-time thing.' I smiled and bit my bottom lip. I pulled my hoodie over my head, revealing my crop top underneath.

'Have you got your nipple pierced?' He asked laughing when he saw it through my top, I didn't respond to him, I just smiled.

'Are we okay here?' I asked him. 'If your Mom comes in, she can't see what I'll be doing.'

'No, you'll be fine,' he said as he unbuttoned his jeans. 'You'll just have to duck so she can't see where you are.'

I climbed down onto the floor in between his legs and hiked the straps of my thong up so they were above my joggers. Joey was now pulling his jeans and boxers down, revealing a major surprise to me. Joey was fucking hung. It laid flaccid against his stomach and must've already been about 5 inches and I had no idea how big it would go when he was hard. 'Fuck me, that's huge,' I said when it came into view.