Sweet Wednesday Ch. 02

Hands shaking, I pulled my phone out and checked the text. Surely enough, it was from Eva.

"Hey baby, so glad you got in touch. What took you so long?"

"I'm really sorry, kind of a long story. But I'm here now and I'm definitely keen if your offer still stands?" I replied instantly.

The message showed up as Read straight away and those three little typing dots flashed up. She was here and engaging with me. It was happening!

"Of course it does. I think you're just like me and I want to help you. But also, you're pretty sexy too baby. When are you free?"

I couldn't believe the honour she was bestowing on me saying I was anything like her. How could little old me be anything akin to her? And she wanted to know when I was free. I wanted to reply that I was free NOW, could I come over NOW, fuck me NOW Eva! Fuck it, what was stopping me?

"I'm just at a club with some mates, pretty drunk to be honest, but I could come over now?"

I sent the text. What's the worst that could happen? Well she'd read it and not instantly replied, so in my dumb little head I obviously assumed she'd reacted badly and I'd fucked it all. Within a minute though, she had replied with an address and three simple sentences.

"I'm at a bar too but will be home in twenty minutes. Call me when you're here, baby. Don't be late."

I had to reread the text to make sure I wasn't imagining it. No, it was definitely real. And now I was in a hurry. I bolted up out of my corner and went to say my goodbyes to the group, saying I had probably had too much to drink and needed to go home and sober up if I had any chance of waking up alive tomorrow. I hugged them all, giving Curtis a particularly affectionate squeeze and promising to text him tomorrow. Five minutes later, I was cruising through London in a cab, bound for Eva's place.

A whirlwind of emotions flooded my brain on the drive over there. Utter excitement at the idea of worshipping her feminine body the way I had in that basement last week. Total anxiety that I was in way above my head. My clitty in my trousers growing harder thinking about being on my knees in front of her. Finally, there was some discomfort there around how different I was going to look from the last time we saw each other. Maybe it would be best to text her to let you know.

"Hey, I'm in a cab now, won't be long. Just so you know, I'm not dressed 'as Amy' today, so I'll be turning up as a guy. I hope that's okay?"

"Of course baby," came her reply a couple of minutes later. "I maybe have something your size you can slip into if that would make you feel more comfortable."

"Yes please, that would be amazing." I typed back as far as my fingers would let me.

We were driving through West London now, a part of the city I wasn't too familiar with and definitely out of my price range.

"Here we are, mate." The taxi driver announced our arrival and I handed him a £20 note, telling him to keep the change in my inebriated gratitude.

I was standing outside a block of flats with a keypad in front of them and a shining metallic silver door. Nervously, I dialled Eva's number and a soft, breathy voice answered.

"Hello Amy. Number 21, I'll buzz you in."

I pressed the button and duly there came a buzz, allowing me to push open the door and enter. Luckily there was an elevator and I got in and rode to the second floor. When I stepped out into the corridor, I could see the doors lined out from 20 to 29 along the hallway. I took the opportunity to take my last deep breath before I descended into more delights as Amy and then gently knocked on the door showing 21.

The vision that greeted me was even lovelier than I remembered. Outside of a dingy basement, with considerably more clothes on and more at home in her natural setting, Eva gave off an aura of supreme confidence and ease in herself. Her chesnut brown hair fell just past her shoulders, tickling the collar of her white cotton button-up shirt she was wearing, with rolled up sleeves and a couple of buttons undone to show off her modest cleavage.

Her slim figure was hugged by a pair of black jeans and her make up was once again natural and subtle, with the only showy aspect being her pronounced and defined painted lips. Her eyes twinkled in a way that suggested to me that she'd had a few drinks and was tipsy. I couldn't help notice that she was wearing what could be considered by some to be a fairly masculine outfit. But then again if you looked as naturally feminine as she did, you probably didn't feel the need to combat any dysphoria with societally recognised female clothing, unlike some transsexuals. Eva broke off this mini gender analysis in my head with a simple greeting.

"Hi Amy. Would you like to come in?"

I stepped in and she shut the door behind me, taking my jacket and hanging it up on the back of the doorframe. Given the part of town we were in it was hardly surprising, but her place was gorgeous. It was all one room, kitchen, dining room and lounge area all in one large open space, with three doors to the sides for what I assumed were two more bedrooms and a bathroom. The floors were wood panelled and the furniture was all clearly not standard flat pack, but had instead been picked out with care.

From behind me, I felt two soft hands fleetingly rub my shoulders before she appeared in front of me again, heading over to the corner of the space where the kitchen was located, complete with an island table which she strolled over to and pulled out a bottle of wine from a shelf built into it.

"Can I get you a drink?"

"Yes please. Can I just have whatever you're having?"

"Oh you are compliant, aren't you?" She teased.

She fished out two glasses and poured us both a red wine, then brought them over to a black leather sofa. She sat down and beckoned for me to join her. I took my wine, thanking her and sipped nervously.

"Amy, I'm so glad to hear from you again. The way you bolted out of there, I doubted I was going to get a reply."

"I'm sorry about that, I really am. It was all very intense there and after I came, everything just felt wrong. It was nothing personal, I absolutely promise."

"Don't worry, honey. I understand. When you're starting out on your journey, women like us, we wrestle with SO much guilt. I wanted to help you with that, that's why I was so keen to give you my number."

Something in her words, women like us, didn't sit exactly right with me but I didn't want her to stop talking and stop being interested in me. I just couldn't believe I was really here. My hands were shaking hard. Eva reached out her fingers gently to steady them.

"Are you okay Amy? You seem a little on edge."

"I'm okay, I'm just so happy to be here. You're so beautiful and I don't really understand why you've asked me here."

Eva's face softened into a gentle, knowing smile.

"I told you, I see a lot of myself in you. Before I transitioned, I was hanging around disgusting clubs like that place I found you and putting myself in danger all because I wanted to be a woman so bad. I know what it's like. And I want to help you. Help you become Amy, the woman you were meant to be."

The question that immediately came to mind though was did I want to be a woman? I definitely wanted to be a sissy slut. Somehow without knowing exactly why I knew that wasn't quite the same as becoming a woman, being trans. Before I could put this to Eva though, she slowly raised a finger and brought it to my lips.

"But also if I can say selfishly, I've also been thinking a lot the last few days how talented these cocksucking lips are."

Her finger probed the entrance to my mouth and I instinctively began to gently suck on it. My body began shaking even more with how turned on I was.

"Mmm, good girl, Amy."

There it was again, my trigger word, that phrase that could send my cocklette from soft to diamond hard in seconds. It was all too much and my body gave a little involuntary spasm, and my wrist twitched. Red wine spurted out of my glass and onto my top.

"Oh shit, I'm so sorry Eva!" I squealed, standing up to make sure none of it had got on her furniture.

"Don't worry, I think you caught it all on your shirt."

I looked down to see a great big red stain all over my white tee. Serves me right for wearing white tonight I thought.

"Why don't you let me put that in the wash for you?" Eva kindly offered. "I said to you before I might have something of mine you could slip into, well it's lying on the bed for you."

"Thank you so much Eva, I don't know what to say!"

"You don't have to say anything Amy. Now let's get you out of that."

Gently, I pulled the sticky t-shirt over my head, leaving me standing there in just my jeans presenting my bare chest to Eva. As a sissy's should be, it was completely hairless, not that I'd ever have to shave it. Eva smiled and stroked one nipple.

"Go in the bedroom and try it on. I'll be with you in a minute."

Eva's bedroom was just as stylish as the rest of the flat. A king sized bed took up most of the room, with black sheets and pillows. The cream coloured walls were adorned with various pieces of artwork but aside from that the rest of the room was pretty bare, although minimalistic rather than boring. On the far side of the room, a large wooden wardrobe took up the whole wall space. Who knew what treasures were stashed away in there?

My eyes fell upon what had been laid out on the bed for me. There lying on the black sheets was a baby blue lace chemise, or was it called a babydoll? Whatever it was, I couldn't wait to slip into it. Off came my jeans and my boy boxers, which seemed disgusting now in comparison to what was coming next. Freed from its confinement, my dick was standing to attention, it too desperate to feel the caress of lace. I took the chemise by the dainty shoulder strings and stepped into it, pulling it up my naked body. When it had all settled into place, the hem stopped just above my knees. As I was admiring myself in the mirror, the door clicked open and in came Eva.

"Don't you look wonderful, Amy?"

I blushed as she slowly stepped towards me.

"But if you're really going to pass, we're going to have to do something about this."

Her hand floated down to my waiting cock. Her small hand enveloped it and I felt it throb back in appreciation of her touch.

"We need to get this down if you're going to be able to tuck. Good job I know a way of solving that problem."

Eva held my gaze and I gulped. She began to lower her body and she slowly sunk to her knees before me. She gathered her hair and pushed it out of her vision and then opened her mouth to take me inside of her. I couldn't help a short sissy gasp escaping my lips. As far as receiving oral went, I was a total virgin. In all my Grindr hookups so far, I had made clear to the guys that they were the alphas and I was the beta sissy and as far as I was concerned I was here to service them and not the other way around. And in fact, the only time anyone had ever really stimulated it was when Eva herself had made me cum at Sweet Wednesday. Again, here she was, taking another one of my firsts, starting to blow me as I stood above her panting softly.

My clitty was swelling in her mouth as she began to apply sweet pressure. I saw now why the guys I did this to loved it so much and I just wished I could return the favour.

"Eva, hang on a sec? Do you think we could maybe 69?"

She grinned wickedly at me.

"You read my mind, baby."

She raised herself up off her knees and began to unbutton her shirt even further. Underneath I could see a dark green bra holding her B-cups. Turning on the spot so her back was to me, she asked.

"Would you do the honours?"

Unlike some of her other male conquests, I'd had enough experience taking off bras, albeit off myself and I slipped it off with ease. When she turned back around, her gorgeous brown nipples were pointing up at me. I couldn't help picture the last time I'd seen them I'd just shot my cum onto them. Gingerly, I bent down and took a nipple in my mouth and sucked. Eva just sighed in ecstasy.

Reluctantly I pulled away so Eva could get out of her jeans. She left her panties on briefly so she could tease me with their removal, a matching green pair that were on the floor a second later. Her member was only semi-hard and depsite it being a cock, the ultimate symbol of manhood, there was no denying Eva's somehow had a dainty quality of femininity.

Positioning ourselves was slightly awkward at first, this was another first for me but eventually I found myself lying on my side on the bed, eyes next to Eva's dick. It was as I had remembered it, not too big and perfectly in proportion to her petite frame. As if in sync, we both leaned forward to take the other in our mouths, both emitting little coos of pleasure as the other's tongue swirled over the tip.

I would love to say we did that for hours, orally pleasuring each other side by side until we both came in unison. However being the oral virgin I was, it really wasn't long before I felt that familiar feeling of the orgasm creeping up on me. I tried to give a warning but my mouth was too full with Eva's hardness to get any words out.

Before I knew it, the dam had burst and for the first time in my sissy life, I was cumming down someone's throat and not the other way around. I filled Eva's mouth with spurts and spurts of hot semen. When it subsided, she pulled away and grinned at me.

"Wow Amy, you do have a big load!"

"Haha, sorry! I really want to finish you off as well though."

"Are you sure? You don't have to if the vibe has gone for you now?"

"Are you joking?" I wasn't going to waste any opportunity to taste her. "You just lie back against the pillows and let me do the rest."

"OK, OK, no arguments from me. You are one keen girl though."

Every time this woman called me a girl my heart sang. We sat up and changed position, her now lying on her back with her body slightly propped up on the pillows, me lying between her legs with her cock filling my mouth. And while it was maybe not hours, this time I can proudly say I was able to pleasure her, slowly and surely, for a considerable period of time, maybe an hour. She'd pause sometimes to check I was still into this and wanted to keep going. Absolutely I did, all I wanted was to give Eva the long, slow, drawn out, sloppy blowjob she deserved, to thank her for everything she'd done for me. I was still wearing the chemise she'd lent me and to thank her for that, I wanted to make love to her genitals. Besides, unlike some of the well-endowed guys I met with, her dick was on the smaller side, so jaw ache wasn't a thing to worry about thankfully.

I'd mix it up every now and again with a kiss to her thigh or a lick of her balls, before going back to the main prize. I couldn't get enough of the taste of her precum. Eva ran her hands through my hair as I bobbed up and down on her, gently guiding me where she wanted me. I loved that feeling, loved being used by her, like my face was just her fucktoy. It was maybe 3am by this time honestly, and I honestly felt like I could do this till sunrise, until Eva interrupted that thought.

"Are you sure you're okay to keep going, it's been ages babe?" Eva asked, propping up her neck to look down at me.

Jokingly annoyed, I removed her from my mouth and told her frankly.

"Will you just shut up? You're getting an amazing blowjob right now and you will until you cum, stop fretting about me! I'm fine. Please take your time. I wanna do this for you. I love doing this."

"OK understood. I just don't want you to feel you have to and I've never met anyone who loves to pleasure me as much as this before. Ever."

"Well I don't feel like that. So just enjoy!"

She laid back and I continued my work with devotion. Over the next couple of minutes I felt her body begin to shake and convulse more and I knew she was approaching the point of climax. I picked up my pace and began to cup her balls gently, which Eva clearly loved by the sounds it produced.

"I'm gonna cum, Amy. Oh god, I'm cumming. Fuck, I'm cumming. FUCK!"

Heat and sticky cum flooded my mouth and dripped down my throat. Like a dutiful sissy I made sure I swallowed it all and didn't remove her dick until I was sure every last drop had been squeezed out of her. When I was satisfied with a job well done, I slid her out and licked my lips. Eva was just lying there, her hair a mess and her eyes glazed, looking at the ceiling. When she came down to earth, our eyes met as she mouthed a silent thank you.

"You know Amy, when I said I was missing those cocksucking lips, I wasn't lying but I couldn't possibly have hoped for something that good!" She shuffled over from the centre of the bed onto one side and patted the pillow for me to join her.

After sidling up next to her, she pulled me in for a deep, passionate kiss. My mouth was still full of her cum, there were still undoubtedly traces of my load on her tongue but neither of us seemed to care. It had been a while since I came and I'd started to get hard again. Eva noticed and reached down to give me a teasing stroke.

"Are you ready to go again?"

"Hehe, I guess so," I giggled.

"Do you want to fuck me, Amy?"

The question threw me. For a total bottom bitch like me, the thought of topping someone else had barely scratched my mind before and I said so to Eva.

"No worries, I'm mainly a bottom but I do vers too. Maybe another time."

"Maybe. Besides I think I'm so tired after today I don't think I'd have the energy."

"How about just me playing with you like this? Eva said, fondling my cock.

"I'd love that Eva."

I laid back and Eva put her free arm around me, so that I was cradled into her chest while the other hand gently pumped my cock. Her hard nipples were in my face and I licked them slowly, enjoying how different they felt to the usual coarse and hairy chests of the men I had hooked up with before. Her breast under my tongue was so soft and smooth, so decidedly female. I was just envious that I didn't have any of my own but the way things were going maybe I would one day.

"Mmm is that nice Amy?"

I moaned my approval. Eva was getting me closer and closer to cumming again. I could tell the second orgasm wasn't going to be as powerful but it would still be delicious. Eva was cranking up the dirty talk now as she milked me. I closed my eyes to heighten my senses.

"You're so sexy Amy. You're a beautiful young woman."

"Am I a good girl?" I pleaded.

"Oh, such a good girl. You'll do whatever I say, won't you?" I nodded vigorously.

"Yes, I'm pathetic. A pathetic little slut."

Suddenly the pressure on my cock stopped, the rhythm broken. What had happened? I opened my eyes to see Eva looking at me with concern.

"You're not pathetic, Amy! Don't say that!"

"Oh no, don't worry, I like it. It's a bit of a turn on for me to hear that."

Eva looked as if she completely didn't get it, if anything she just looked worried.

"Do you want me to stop?"

"NO!" I begged. "No, no, please don't, I'm so close."

She nodded and moved down my body, wrapping her lips around my cock again and started to give me a powerful blowjob, milking me dry. I squealed and a wave of flutters came over me. Clearly it was not as much cum this time, as when Eva surfaced and licked her lips, her mouth was clear. Completely spent, I lay back on the bed. Eva moved off it and walked over to the wardrobe. She pulled out a chemise that was almost identical to mine but for the colour, hers pink.

She snuggled into the bed with me and pulled me close into her so that we were spooning. Neither of us felt the need to say anything necessarily, we both just basked in our post-orgasm glow, totally content to lie in silence with our sticky bodies pressed together until sleep took us. I still didn't know what I had done to deserve such an experience but as I drifted off into my dreams in her arms, I felt like the luckiest sissy in the world.