The Wife Ch. 02

To Whomever The Hell You Are,

So, apparently this was a good start. When I showed this to my therapist, she seemed to think so. She said I've started breaking ground. Even still, it's taken me a month of courage building to get the nerve to continue these. Like the woman said though, gotta start somewhere. So here I am, back at another letter to you, my former self. Still think it's a little cheesy but my therapist says life without a little cheese is dull and honestly, I do like it a little cheesy.

I thought long and hard about what I saw that morning. Quite often, too. I would imagine their voices, whispering in my ear as I masturbated to their sight, and each time would send shivers running through. That initial feeling of excitement though grew into something more. It became a hunger that I wasn't going to fill just by masturbating to the memory. I needed more but I was still a little nervous. This whole thing would be much more overwhelming if I stopped to process, but I was swept up in the cravings.

Only problem was, I couldn't decide how to fill that craving. I was too shy and new to just ask another man out and dating apps like Tinder were always a bust in the past. I tried supplementing the feeling by browsing porn, but that only touched the surface. Every time I finished, I would be ready to go again. The hunger only intensifying as the day's drew on. Eventually, I found myself perusing porn when I found a link to a website.

'Tired of dating apps?'

I'd seen plenty of these sites before. Post an online ad and someone in your area can message you to meet. I'd always thought they were redundant but since dating apps really hadn't been working and I was getting desperate to find a way to satisfy this newfound hunger, I clicked.

Somewhere in the back of my mind, there was a little voice saying it was a bad idea, but I ignored it. Found it pretty easy, too. Once I entered an approximate area to search, I found several profiles of men, looking for someone to spend the night, or an hour, with. That voice seemed too far away now. I spent hours searching. I had no idea where to begin or what to say once I did, until I decided the easiest way would be to make my own post and have them come to me.

It was easy enough to make a post, all I had to do was put in that I was looking for someone to have fun with. I included that I was new to having sex with guys and that I wanted to find someone to help show me the ropes. Surely they would line up for a newcomer. The hard part was the anticipation. Everyone likes to think they're super attractive and I'm no exception, when I made that personal ad, I thought I would have mountains of replies withing seconds. It took four days to finally get a message and the message was short.

'Are you real?'

The excitement of getting a message faded pretty quick. Not an altogether unrealistic question, but not quite the one I had been expecting. I had been expecting flirting, or a witty remark. Something I might have opened up with on Tinder. Which, thinking back on now, is probably why I didn't have a huge amount of success on there.

'Yes, I am real.' I typed, not knowing what to say.

'If ur real, why no pic,' the messenger responded.

I hesitated. Partly because the sudden change in spelling and grammar, and partly because I hadn't thought of putting an image of myself with the ad. Did I really want to put an image of myself for some stranger on the internet?

'I'm not sure I want my face out there,' I replied.

'Not your face,' the response came, 'ur body, heres mine'

As soon as the picture loaded, I noticed his most distinguishable trait was his manhood. I don't know how long I stared at that monstrosity, admiring the girth and length. It put my own to shame by a long shot. Not that I was small by any means, at least at that time, before the transition. This thing could choke the life out of me just by looking at it. I could imagine it in my hands, growing and twitching, ready for me to...

'Do u like,' a new message flashed, bringing me back to reality.

'Yes,' I replied, noting the stiffness in my own jeans and the drool on my chin. It was unmistakable at this point.

'Show me u.'

I hesitated again. This could be anyone. That could be anyone's picture. The greed of my lust took over my thought process though. What harm could this do? It's not like my face was going to be attached. Besides, I told myself, it's not like I have to meet the guy. I could just see where this goes. With that thought fueling me, I eagerly stripped down and took a photo of me in the mirror. Making sure to show my stiffness as well.

Comparatively, he was definitely bigger than me, not just in the size of his cock, but he looked taller, more manly. Even if he was more average build. I on the other hand was short, about 5' 5", and had way less definition in my muscles. I wouldn't say feminine at that time, but definitely not manly. It was because of that though that as soon as the picture was sent, the panic set in. I wasn't manly enough to like men or he would think I wasn't enough. Until the reply came through.

'Looks like ur all ready to see me now, lol,' the message read. 'u look delicious.'

I could feel my cheeks redden and burn.

'Well, you're quite something to be excited for,' I sent, feeling both stupid and flirtatious. Luckily, he liked it.

'I like what I see, too,' he said and a video popped up of him stroking himself to what I assumed was me.

'Is that for me?' I asked.

'If u want it to be bby,' he replied. 'Let's meet.'

My heart froze. So soon? No coffee date or dinner just an exchange of pictures and he was ready to go. Part of me wanted the traditional date but a greater part found the whole thing hot. The lustful side won.

'I would love to,' I typed.

'Cool,' the reply came followed by an address. 'Let's meet here, its easier to go from there. 8 pm.'

'See you then,' I said.

8 PM was only an hour away, not leaving me much time. Although I knew this wasn't a date, I still wanted to look semi decent and threw on some clean button up and a new pair of underwear and jeans. Twenty minutes later, I was dressed and ready to go. The jeans felt a little tight, but I couldn't tell if they were just smaller than I remember or if my cock was busting through from excitement.

I didn't waste anytime, heading straight to the address. Turned out the place he wanted to meet was a hotel restaurant. It was one of the nicer ones too. I checked the site messages on my phone, nothing. I was still a little early, but my nervousness was playing hell with my anxiety. Telling me that he wasn't coming, that I was a fool and I wasn't brave enough anyway, until I heard the ding of a new message.

'R u here?' it read.

'Yes, at the entrance,' I said. I looked around to see if I could spot him, but there were so many people and without a face to the body, I was lost. Suddenly, I felt a tap on my shoulder. I spun around to see an attractive face on an even more attractive body. Even before he spoke, I knew this was the man. My reaction surprised him as if he didn't expect me to recognize him. Honestly, I surprised myself, as a small bout of anxiety was still telling me to run as fast as I could.

"Are you looking for someone," he asked. "Perhaps a strapping young fellow?"

"I suppose I am," I sputtered nervously. "He told me to be here at 8, you wouldn't know where I can find him?"

The man laughed heartily, turning several heads.

"That would be me, babe," he said. I shivered at 'babe' getting a soft reminder of the muscular man saying 'sugar.' I thought it strange, but I liked it at the same time. The confidence was definitely needed because otherwise, I might've screamed at my own lack thereof. He motioned me to the bar of the restaurant. I was relieved it wasn't going to be a sketchy encounter and that we would talk first. It eased my nerves a bit as the bartender handed me my drink order.

"My name is Tom, by the way," Tom introduced himself.

"I'm Max," I said.

"So I take it this your first time," Tom said, sipping his whiskey sour.

"Sort of," I replied, not wanting to sound, perish the thought, inexperienced.

"Sort of?" Tom scoffed with a light chuckle. "What the hell is a sort of?"

Tom never broke his attention from me. He had a sort of directness and attentiveness that made me feel like every word I said was super important and that he didn't have time for anything else. The most complex emotions I've never felt before washed over me. I was intimidated but fascinated by him. His green eyes pierced through mine as if searching for everyone of those feelings and he wasn't going to be satisfied until he got them.

"I..." I started. "No, this is. I'm just super nervous."

Tom laughed knowingly, helping relieve some of that nervousness.

"How did you know?" I asked.

"Your ad, love," he said, smiling. "You mentioned in your ad."

"Oh, right," I smiled sheepishly. Tom didn't seem to mind the slip of the mind though as he continued to probe me with his eyes. I couldn't help but blush, which surprised me, because I never really blushed before. Which just caused me to blush all that much more.

"You look so cute blushing so hard," Tom said. Goddamn he's coming on strong, I thought.

"Don't worry," Tom continued, placing his hand on my knee. "Everything is up to you tonight. I was right where you were once too. I'll help you."

I smiled, reassured by his calm demeanor.

"I don't know where to begin," I said.

"Well, lets start with what you like," Tom said, taking another swig from his drink. I realized that until now, my vodka cranberry had sat mostly untouched. I didn't want to get carried away but liquid courage didn't sound too bad either.

"I don't know," I said sipping my drink. "I've never had success in the sex department."

"Well, that just means you need a wonderful teacher," Tom smiled. "Lucky for you, I am a wonderful teacher."

He gave a little wink at the end causing me to blush again.

"Really," I said, feeling warmth in my cheeks.

"Really," Tom responded, moving his hand from my knee to my hand. I breathed in as I let him hold it. "Do you want me to be your teacher?"

"Yes," I breathed, as he drew in close. His cologne was intoxicating, filling my nose as he drew in and gave me a soft kiss. I wasn't expecting a kiss but I didn't resist as his lips met mine. Even though he was clean shaven, I could feel a small tickle from some stubble, which sent shivers down my spine as he gently put his other hand on my cheek to draw me in closer.

You know that feeling after a first kiss, where sparks fly and you're left seeing stars? The rest of your body goes numb with anticipation. I felt three times that sensation. It was as if I had spent my entire life thirsty and had just now found a way to quench that thirst, and each moment Tom held that kiss felt like an eternity. When he broke that kiss, I was already melted breathing in as if to fill my lungs with air that he had stolen from them.

I had never felt this way before. It was like I had opened my eyes to see me, the true me. I didn't resist. I drew back unwillingly, wanting more of his lips. His smell, his hands. I was crossing a bridge I couldn't uncross, and I was ready to cross it for him.

"I have a room here," Tom said. "I got one just in case, if you still want me to teach you."

"I think I do," I said.

It was all I could manage not to throw myself on top of him here. I was overcome with lust and horniness. I didn't even know all that much about him, but I felt strangely safe. I can't explain it, even to this day. Some people you meet just make you feel that way. I followed his lead to the elevator, his hand in mine guiding me. There were other people in the elevator, all doing their best to ignore one another, which was easy for me as Tom was running his fingers along the skin of my arm.

Finally we reached his room and before the door to the room was even shut, I couldn't take it anymore, I needed to be kissing him. I needed the feeling that I felt in the bar. I didn't get that feeling though, it got better. Tom pulled me in close and twirled me against the wall, never breaking the kiss. I let out a small gasp that was muffled by his tongue entering my mouth. His hands ran down my sides gently and firmly feeling every inch of my torso. All I could do was hold onto him, my arms curled around him as he sandwiched me against the wall. His hands finally found my crotch that was nearly bursting out of my jeans. I could feel his own pushing against me, though as he was nearly a foot taller than me, it pressed just above my own. Tom finally broke the kiss, leaving me gasping for breath.

"Remember," Tom said, pulling me towards the bed. "Tonight's about you. It's important to know each other's limits. If you feel uncomfortable, you need to say so."

"OK," I said, reaching for his face again. He smiled and leaned in to kiss me again. This time leaning me back onto the bed as his lips met mine and our tongues leapt to dance with each other. I felt his hands exploring my body again and then gently undoing my belt and jeans. I shifted to help him, not wanting to stop making out, but desperate to free the stiffness in my pants. Tom pulled them off so smoothly, I was caught off guard by the sudden air on my legs, and I realized, my underwear had come off as well.

Tom broke away again to look at my cock which twitched eagerly for him. I was so excited, precum was already leaking out of it. He reached down and gently grabbed it, using his thumb to swirl the precum around. I gasped as a wave of pleasure shot through my body as his thumb made circles the head.

"Someone's excited to be here," he smirked. "Let's give him a proper introduction."

Shifting his position, Tom took my whole cock into his mouth and started to suck it while his hands began exploring my legs. One found my balls and when he cupped them, I tensed up. The pleasure mounting from each second he moved his mouth up and down my shaft and the gentle massage he was giving it's two companions. The pleasure was too much and I couldn't contain it.

"Tom...OH SHIT.... TOM, I'm gonna...FUCK!" I exclaimed as he squeezed my balls firmly while I shot load after load into his mouth. It was the second time I had the best orgasm of my life.

"Oh fuck," I gasped. "I'm so sorry, I can't believe I came so fast!"

"Don't worry about it," Tom said, licking the excess cum of his lips. "We're not done yet."

"But..." I started, but Tom just pressed his lips to mine. I could taste my cum on his breath, and at first I thought I was going to be disgusted, but the opposite happened. Even though I had just cum, my cock was still rock hard and the taste of my own cum was making me go crazy again. God what a kisser, I thought. I was so caught up in the new taste of his kiss that I didn't notice he had taken off his own pants. My hands started to explore him, mimicking the paths he had just taken on me. That's when I felt it, his massive cock stretching up to my hands. I gasped and broke away my eyes staring at his impressive tool.

"He's been dying to meet you," Tom said, guiding my hand onto his cock. I instinctively wrapped my fingers around it. He was so thick that I could barely fit my fingers around. I gave it a small stroke and he twitched in anticipation.

"Your fingers feel so nice," Tom breathed. He pulled me close and kissed me as I stroked.

"Do you want to taste it?" Tom asked. I could only nod in answer as I was hypnotized by the whole sensation. Tom shifted into a position to make it easy for me to access. My heart was pounding, and each breath seemed to fill less and less of my lungs. I could feel his body heat emanating from him mashing with my own. He smelled sweaty, especially as I got closer, but it just turned me on even more as he guided his cock to my lips, I remembered some of the videos I'd seen before and tried to mimic that.

I opened my mouth and welcomed his cock in. The first thing I noticed was how full it filled my mouth, and how right it felt. The second was the taste, it was salty. It didn't have a dirty or a sweaty taste, just like salty skin. I thought that I was going to hate the taste, but I loved it. I eagerly went down as far as I could, wanting to take him all in as he had me. But before I could reach the base, his cock hit the back of my throat, causing me to gag.

"Slow down, babe," Tom said. "You're not ready for that kind of thing yet. Take it slow. Go down as far as you can and repeat that. The rest will come with practice."

"Are we going to practice a lot?" I asked hopefully. Surprised at myself.

"As much as you want love," Tom responded. "First, take it slow. Enjoy it and savor it."

I did as he instructed. Lowering my head to just the point where my gag reflex wanted to kick in and returning. Pretty soon, I had a pretty good rhythm going as I sucked as hard as I could.

"Oooh, that's it baby," Tom moaned. "Not too much teeth now, there you go."

I felt his hand run through my hair as I bobbed. His touch caressing whatever part of me he could find. I loved his touch, encouraging me as I blew. After a few minutes, Tom effortlessly pulled me up into his arms, kissing me firmly.

"I hate to take away from those fucking awesome lips you have, but I need you," Tom said.

"You mean like..." I trailed off.

"Mmmmh, baby," Tom said. "Only if your ok with it."

Up until now I hadn't thought of having someone fuck me in the ass, but now that it was here, I wanted nothing more. Tom turned me onto my back and in one smooth motion had my legs spread as he massaged my asshole, which clenched in anticipation.

"Hmmm, you look so beautiful right now," Tom said. I couldn't understand how as all I could focus on was his fingers massaging my hole. Wave after wave of pleasure with each pass he made. Followed by a sudden cold wet feeling. I glanced down to see a bottle of lube in his hand and suddenly his finger was pushing the lube in. I gasped at the sensation as it sent a fresh wave of pleasure. Tom quickly applied a condom and more lube, only pausing just as he was about to enter my ass., looking me deep in the eyes.

"I'm going to start slow, and gradually pick up speed," He said. "If it's too much let me know and we can slow..."

"Please just fuck me already," I gasped as I felt his cock pressing. I couldn't wait anymore, I needed him now. He smiled and laughed.

"All right then, love," Tom said and slowly pushed into me.

A blast of pain and pleasure crashed into me. I gasped audibly arching my back, pushing him farther in, intensifying the feeling. I felt all the pressure as he pushed in and stretched my virgin hole. I could hardly believe it when I looked down and he was almost all the way in. His massive cock sat there filling me as Tom paused giving me a moment to get used to it, before he began pulling back out.

Gradually he began to thrust, taking my moans of pain mixed with pleasure as a sign to continue. Each thrust of his cock would tap back of my ass, causing intense waves of pleasure to course through me.

"OH GOD!" I screamed. "OH FUCK, THAT FEELS GOOD."

Tom smiled and pumped harder, increasing the pressure of pleasure that was building inside of me. His hands held my hips in place as he leaned in to kiss me again. I sank further and further as each thrust made it difficult to maintain. I yelled out in pleasure again.

"FUCK TOM! HOW ARE YOU...OH FUCK! FUCK ME HARD! PLEASE DON'T STOP FUCKING ME."

He increased his speed and I could feel him begin to tense, his balls slapping my ass. I heard him grunt with each thrust until he gave one final push. He groaned as he filled the condom in my ass, which sent me over the edge. I came so hard it shot up and hit us both in the chin as Tom held his head close to mine, until he collapsed beside me. I lay stunned, as the orgasm was still washing over me. So many new things today, it was hard to appreciate that not only had I cum twice, I had cum from being ass fucked.