Miss Alyssa's World Ch. 01

Another boring Friday night on the horizon! I had been single for 6 months now. After a solid 10 year relationship, Emma and I had split up. We had a good run, but we both agreed that over the years, we had transitioned from passionate lovers to best friends. I was still in contact with Emma, but our chats were always friendly; no more flirting.

I'm far from being vain, but I consider myself to be a pretty good looking guy. 6'1, 180 pounds, good abs and tight pecs, dark black hair and green eyes. I take care and pride in my body and image. I train everyday, either in the gym, running on the track or cycling in the trails. I don't drink too much (except red wine and a few cocktails), but I do enjoy cannabis edibles. After all, they are legal here in Canada.

Montréal's nightlife can be fun and crazy. I sometimes go out with my friends or colleagues from work, and I did end up going on a few dates in the past few months. However, nothing really clicked. I'm looking for that special connection, and for some reason, I can't seem to find it.

About a month ago, I met this girl on Tinder. Alyssa. Oh Alyssa. Funny, energetic, flirty, smart! She's about 5'7, has dark black hair and deep blue eyes, a lean figure, a nice tight ass and firm small tits. We have so much fun. We share similar interests when it comes to staying healthy, and she works in the same field as me. I'm a nurse at one of Montréal's largest hospital; she's a psychologist in another hospital. Needless to say that this helps, because Alyssa understands my sometimes difficult work schedules.

We text many times a day. We have shared pictures, but no nudes yet. I love the way things are going. I feel super comfortable sharing my most personal thoughts with her, and she does as well. Honestly, I see a possible relationship with Alyssa, and I can't wait to meet her.

Last weekend, our chat took an unexpected turn. Alyssa asked me about my fantasies and kinks. We talked about the type of porn that we like to watch, and discussed our deepest desires. She told me that she always felt as if she had an unexplored dominant side. I answered that I was curious to learn more, but I didn't go as far as telling her that I have been jerking off to femdom porn for a few years now.

Alyssa then asked me what I thought about wearing her panties. I laughed and blushed. Although that was kind of hot and kinky, I had actually never considered wearing girl clothes. I basically said that with the right girl, I might do it, but that I would definitely need some encouragement. She sent me a photo of her in her silk pink panties, and told me that I would look amazing in them.

I wondered if Alyssa had been drinking that night, because it was the first time that we had this kind of conversation. It was hot and intriguing and I admit that I jerked off to her picture, imagining what this kind of experience would be like.

So back to my boring Friday. I was off for the weekend, and didn't have any plans yet. And then, a message from Alyssa.

''Hey sweetie! I think it's finally time we meet in person. I don't have any plans this weekend. Wanna come over, either tonight or tomorrow night? We could have wine and chat. Let me know what you think!''

''Hey Alyssa! That sounds like an amazing plan! I was actually feeling depressed about another boring night by myself. I can pick up some sushi and few bottles of cab sav and meet you at around 8, if that works for you?''

''Yes, that works for me Danny! I'll send you my location. Talk soon!''

The day went by pretty fast. I made sure to groom myself, and chose my favorite clothes. My wardrobe is very simple: I love dark blue fitted jeans, and fitted white or black tshirts. It might sound boring, but that's my style. I hesitated between my white sneakers or my Dr. Martens boots, and decided to go with the boots. I put my favorite perfume on, and made sure that my hair looked good.

I was a little bit nervous about meeting Alyssa. I was really, really into her, and I didn't want to screw this up. Plus, Alyssa had told me that she was seeing this guy for a few months, but that they had recently decided to stay friends. Dating was definitely not easy.

I walked out of my building, and walked to the closest Société des alcools du Québec (our liquor stores). I grabbed two of my favorite wines. I then stopped at one of the best Sushi restaurants on Rue Sainte-Catherine, and grabbed a mixed sushi plateau.

Alyssa's place was about 30 minutes away from my place, but only 10 minutes away from the sushi place. She lived in the Village, one of Canada's most important LGBTQ+ districts. The fact that she lived there made sense, because she had an office in the area. She would alternate between hospital work and office work.

When I got to her door, I noticed that Alyssa had a camera doorbell. I rang.

''Hi Danny! So happy to see you. What's the password?'' I heard her laugh.

''Hmm... Ha ha ha. I don't know. Sushi?''

''Nope! Maybe if you beg to come in? Try that.''

I chuckled.

''Hmmm ok, Alyssa, may I please come in?''

''Close! Try Miss Alyssa and we'll see.''

She was in a playful mood! I smiled and tried again.

''Miss Alyssa, may I please come in?''

I heard the buzzer. That was an interesting start to our first date.

I walked up the stairs with a smile on my face. I was really happy to finally meet her.

When I got to her apartment door, I noticed that she had left the door partly open. I knocked and pushed the door open. She was there, sitting at the kitchen counter. She looked up at me, and I froze. Alyssa was more beautiful than in her pictures. She had all the attributes to be a model.

She was wearing a tight black top and black leather pants. Her hair was darker than I expected, and she was wearing bright red lipstick.

When she looked at me, I felt hypnotized. It was the first time in my life that I had this kind of feeling, and I was not able to explain it.

''C'mon in Danny, I'm so happy to finally meet you!''

She took the bottles of wine and sushi, and placed them on the counter. She then came closer to me and give me huge hug. She smelled wonderful. I tried to guess what type of perfume she was wearing, but I wasn't able. Everything was just perfect.

''Wow Alyssa, you look amazing! I'm so glad that we can finally meet in person.''

''Me too, Danny! Sit down, let's eat!''

Our supper was amazing. We laughed a lot, talking about our dating experiences, the weirdos we had met on dating apps, and the struggles of meeting new people. I felt so comfortable with her. She was caring, really took the time to listen to me, and spoke without filters.

When we were done with supper and the first bottle of wine, Alyssa gave me a quick tour of her apartment, and we ended up on the couch with our second bottle of Cabernet Sauvignon. She had also thought of everything, because she had cannabis chocolate just for me.

''So have you always been vanilla, Danny?''

''What do you mean?''

''Well, you sound kinky when we text, but I feel like you haven't have too many opportunities to experience other things. For example, you've only been with girls. You didn't really explore the wonderful world of BDSM. Do you feel like you need to get out of your comfort zone sometimes?''

''Hmm well that's a good question. I mean, when I watch porn, or read stories on Literotica, I don't always pick vanilla stories.''

''Ok, interesting. Tell me what categories you like then.''

I was a little bit embarrassed to talk about that, but I was already tipsy and the chocolate was slowly kicking in.

''Well I mean I have read stories about gay couples, or bi curious stories. I've watched some domination videos. I don't always pic the vanilla stuff.'' I was bright red.

''Ok, that's a step in the right direction.''

She was smiling. I was listening to every single word she was saying. I was clearly hypnotized.

Alyssa got closer to me, and put a hand on my crotch. We started kissing. She was an amazing kisser, and the fact that she kept pushing her tongue in my mouth made me even harder. She stopped and looked at me. She squeezed my cock through my jeans.

''Can I?''

I nodded.

''Hmm of course you can Alyssa.''

''Beg for it baby.''

''Miss Alyssa, could you please touch my cock?''

''Oh I don't want to just touch it. Beg for it sweetie.''

''Miss Alyssa, please, can you suck my cock?''

I couldn't believe that I was saying these words. I had never role-played like this, and it was so hot!

''Why do you want me to suck your cock, baby. Do you like cocksuckers?''

I blushed again.

''Hmm yes, I do love cocksuckers.''

''Good answer, sweetie.''

She slowly unzipped my jeans, pulled down my CK boxers, and took out my hard 8 inch cock. It was wet with pre. She kissed the tip, and then took it in her mouth. Inch by inch. I was surprised at how good she was. She had all of my cock in her mouth. She was looking up at me. I was smiling. I was in heaven. This girl was something else!

She kept on sucking my cock, making loud suction sounds. This made me even more aroused. I wanted to last longer, but I knew I was already close. I didn't know Alyssa too well, so I wasn't sure if I could cum right there, in her mouth. Would she be mad? Did she want me to warn her?

''I'm really close, Alyssa.''

She stopped for second.

''Ok you will beg to cum, sweetie.''

And she started sucking me again.

''Miss Alyssa, please let me cum. I beg you.''

She stopped again and looked at me.

''Ok baby, you can cum in my mouth.''

And as soon as she wrapped her lips around my cock again, I came so fucking hard. I swear, this was probably the biggest load I had shot in a few years. I could hear Alyssa swallowing my cum. She was an expert at this. And then she moved up, and our lips met.

I had never tasted cum before. While I thought that Alyssa had swallowed my load, her mouth was full of my cum when she pressed her lips against mine and proceeded to push all of my cum in my own mouth. She had both hands behind my neck, and there was no escaping. She really wanted me to swallow my load. I had no choice, so I did.

When it was clear that I had swallowed all of it, she stopped kissing me, put both hands on my cheeks, and looked straight in my eyes.

''I think you're a cocksucker too, Danny.''

I turned bright red.

''Hmm well I don't know Alyssa. I mean this was fucking hot, but I love women. I haven't really pictured myself with guys.''

''I think that you have so much to discover, my sweet Danny! You have lived a very vanilla life, and that ends today. Want to experience new things with me?''

One thing was clear, I would never, ever be able to say no to this woman. I was mesmerized by the way she looked at me.

''Yes, I do want to experience new things with you Alyssa.''

''Good! I love that. I knew from the day we met that you would be open to trying new things. You'll get to know me better, and you will soon find out that I'm nothing like your ex girlfriends.'' She started laughing and took another drink of wine.

''Let's play a little bit. Try this.'' She handed me her lipstick.

I was confused.

''You want me to try to apply it on you, you mean?''

''Don't be silly Danny. You're so cute. You know what I mean. Try to apply it on your lips.''

''Oh... ok!''

She handed me a small mirror. The lipstick that she had chosen was a bright pink color. I opened the tube and did the best I could.

She laughed.

''Oh my god, that is so fucking cute.'' She took her phone out and took a quick picture.

''I promise we will look back at this photo one day and laugh! Let me help you.''

And she applied it expertly on my lips. She then showed me the result in the little mirror. It made me laugh, but my cock was hard once again. How confusing!

She obviously noticed and touched my bulge.

''I think you like putting make up on, sweetie. Say it.''

I hesitated.

''I love putting makeup on.''

''You know who loves putting makeup on, baby? Good girls. Are you a good girl?''

I giggled and blushed.

''Hmm well yes, I guess I'm a good girl.''

''I think I'll call you Danielle, or Dani. That suits you well my love! Now, remove those boxers sweetie.''

I did as she told. Alyssa got up, walked to her room, and came back with a pair of bright pink panties and a bottle of perfume.

''Put these on, Dani.''

I put the panties one. I was surprised at how good it felt to have silky tight panties. My cock was rock hard.

''Fuck you look amazing, sweetie! I swear!'' She took another picture. She then sprayed some perfume on my neck.

''That's much better! How does it feel, Danielle?''

''It actually feels pretty good, Alyssa.''

''Miss Alyssa to you, sweetie.''

''Yes sorry, Miss Alyssa.''

I poured two more glasses of wine, and Alyssa turned on her tv. She said it was time to watch a little bit of porn, and she picked videos showing men being turned into women. In one video, the guy was all dressed in pink. He was wearing a pink collar, and was kneeling in front of a woman dressed in a black latex suit. The woman was wearing a black strap-on, and the guy was about to suck it. It was actually really hot.

She touched my bulge once again.

''I think our sexy girl loves what she's seeing. Tell me what turns you on in this video?''

''Well... I mean I kind of like the fact that she's telling him what to do and he's doing it.''

''Yeah, so my little Dani loves it when her woman takes control, right?''

''Yes, well I guess I do.''

''Good girl. And does my little Dani love the fact that the guy will soon have the huge dildo in his slutty mouth?''

''Well I mean it looks hot too I guess.''

''Nice. You're a quick learner sweetie!''

I then heard someone at the door. I looked immediately in that direction, and Alyssa noticed how panicked I was. I wondered who was going to open the apartment door and see me wearing lipstick and bright pink panties.

''Don't worry sweetie, it's my roomie! Mika is super nice. He won't be shocked by what he sees.''

And Mika walked in. He was clearly coming home from a night on the town, and he was very tipsy. He smiled at Alyssa. When he saw me, he smiled but I also noticed something else in his eyes: desire.

''What do we have here, Aly! Your new girlfriend?''

They both laughed. Mika sat on the leather chair, facing the couch.

''Mika, this is Dani, or Danielle. Dani, this my best friend and roomie Mika! Mika works at one of the clubs close to here.''

''Mmmm so nice to meet you sweetie! Yes I work at the bar, but I was off tonight. Had a great time dancing, drinking and flirting!''

Alyssa poured a glass of wine for her roomie.

''I'm just going to go put something more comfortable, and I'll come back and join you guys.''

Mika smiled, winked at me, and went to his room. When he returned, he was wearing tight baby blue underwear and a white camisole. I immediately noticed the bulge in his undies. He grabbed his glass wine, and sat back down.

''So, Dani. Do you only like women? Have you ever played with guys?''

Alyssa answered for me.

''Dani has only been with women, but he tasted cum for the first time tonight!''

I wanted to hide under the couch.

''Hmm interesting! Who's load did you take, you little slut?''

They both laughed.

Once again, Alyssa answered before i could.

''He swallowed his own cum! Dani did a great job!''

I blushed and smiled.

Mika was touching his cock while looking at me.

''Well that was good practice. Maybe you need to try another man's cum now baby, what do you think?''

I looked at Alyssa. She knew I was scared. But she nodded and smiled.

''Go ahead my sweet girl, I think it's a good idea. And this is a safe space. Go on, go suck Mika's penis.''

Mika was smiling. I was frozen. I wasn't sure if all of this was a joke. But I was drunk and high by now. I was also obviously very turned on by the situation, and still had a huge erection in my panties.

Alyssa pushed me up, so I walked towards Mika.

''Go on, get your knees, and take my cock out.''

I got on my knees and slowly took out his cock from his underwear. It was bigger than mine. I felt intimidated. I turned around and saw that Alyssa had taken her phone out. She was recording the scene.

Mika placed his hands behind my head, and slowly pushed my face on his cock. I opened my mouth and took his cock between my lips. I didn't really fully comprehend what was going on. I was so fucking turned on. I was kneeling in Alyssa's living room, wearing pink panties and pink lipstick, and I was sucking a man's cock for the first time.

''That's it, you little slut. You're so fucking good at this for a rookie!''

Mika was enjoying this, so I figured that I was doing a good job.

I kept sucking his cock, and Mika started being a little bit more agressive, almost as if he was trying to fuck my face. He would move his body so that his cock was pushed deeper in my mouth, which made me gag a little bit. But I managed to stay concentrated.

While I was sucking Mika, I heard Alyssa moaning in the background. I didn't want to stop what I was doing, but I kept wondering what she was doing. Was she touching herself? Is this what she liked? Having two guys play together while she masturbated?

''I'm going to cum in your mouth little slut. Are you ready? Are you going to be a good girl and swallow it all sweetie?''

I looked up at him and nodded yes.

And that's when he exploded. He came so hard that I stopped breathing for a few seconds.

''That's right little bitch. Swallow my hot precious juices. You are an amazing cocksucking slut. Milk my cock you little whore.''

I was doing my best to please him. And I still could not understand why I was so fucking hard and turned on. In the meantime, Alyssa was still moaning and I wanted to turn around and see what she was doing.

''Good girl. You did so good sweetie!'' Mika took his cock out of my mouth and slapped it gently on my lips and cheeks.

I looked up at him and smiled. It's hard to explain how I felt, but I was confused by mixed emotions. I was both embarrassed and proud of myself. I mean, I had made a man cum by sucking him, so I kind of felt like I had done a good job.

That's when I turned around and saw Alyssa.

I could not believe my eyes.

My new girlfriend was sitting on the couch, her leather pants and panties down. Her eyes were closed, and she was moaning. She had put her phone down on the coffee table.

She had her left hand up to her lips and was sucking on her fingers, while her right hand was between her legs, stroking... her cock.

My girlfriend had a penis.

She opened her eyes and looked straight at me. She smiled. I blushed and smiled back.

And right then, I knew that I was where I was meant to be. Dani was born, and it was the beginning of a life changing relationship with the most special girl I had ever met.