My wife Dawn had surprised me by saying we were spending the night in as two girlfriends, laying out my clothes so we matched. Then after having amazing sex, Dawn surprised me by telling me that she had invited her friend, Maria, and Maria’s husband, Mark, over for some fun with the two of us and to fulfill the fantasies of all of us.
So I was standing there with my red plaid skirt, white top, and red high heels, and my cock was rock hard underneath my skirt, and my mouth was wide open at this news.
"You invited people over to our house? No one has ever seen me dressed but you, and now people will be here any minute?" I asked in a panic, but yet still excited by it. "And what did you say was going to be happening?"
"Honey, first of all, you look great, so don't be worried about people seeing you. Just trust me. As for them coming over, you and I have talked and fantasized a million times about you being with someone else, especially while you're dressed. And many of those fantasies involved being with a man, so after talking to Maria and she started telling me about what her and her husband fantasized about, it seemed perfect. Her husband wants to in a threesome, and Maria wants to watch Mark with twins. I told her about you dressing, and she was totally turned by it, and she somewhat joked about you and I being the two girls in her fantasy. We laughed for a second, but then I said why not? Next thing you know we were planning it out."
"Wow you're serious aren't you?" I replied. I was stunned, but definitely excited that this may really be happening. This whole idea is definitely something I have thought about a million times but never thought it would really happen.
"Okay honey, they're going to be here soon, so why don't you go freshen up your makeup and I'll get us some drinks" Dawn told me. I re-applied some extra lipstick, brushed up my mascara, and made sure my stockings were staying up. I thought I still looked pretty good. But for other people to see?
Dawn and I sat down and had some of our drinks when the doorbell rang. Dawn answered the door and led Maria and Mark in and headed towards the living room. I was totally stressed and excited at the same time as the moment I've been thinking about was here.
"Maria, Mark, this is my girlfriend Ashlynn," Dawn said to them.
"Hey, Ashlynn, it's great to finally meet you! You look fantastic! I love those shoes, and that skirt looks great too! We should go shopping together sometime!" Maria said to me. This of course immediately put me at ease.
"Hi, Ashlynn. I'm Mark, it's nice to meet you," was all Mark said to me. Although that was all he said, he looked at my breasts. Then Mark looked Dawn up and down and I could tell he liked what he saw and then he said, “Wow, you two are like a hot set of twins,” at which Maria smiled devilishly. Mark definitely didn’t seem to mind that I was dressed as a woman, and in fact treated me like I was one, which was a great feeling.
We all sat around drinking, laughing, and getting to know each other. After a few drinks, Maria came over and started putting her hands on me and stroking my hair. Then Maria started kissing me deeply, and then she even fondled my breasts. I definitely did not expect this but was totally turned on by it. Even though I dress as a woman, and want to be with a man, I am still way more turned on by women, so this was very hot. But Maria had said she wanted to watch, so I was still a little confused.
Suddenly she stopped and whispered in my ear, “I kept thinking about what you are getting ready to do to my husband and just couldn’t resist at least a little kiss.” Then she walked over to Dawn, whispered something in her ear, and then went over to her husband.
I saw Maria and Mark head towards the living room, when Dawn came over, said, “Just follow my lead, then you’ll know what to do from there," and took me by the hand and led me into the living room as well. Maria stopped Mark in front of our sofa, and started kissing him deeply, then she told him to stay there and she went and sat on the loveseat. Dawn led me over to Mark as he was standing there looking us both up and down as we approached him.
We stood on either side of Mark, two red heads in our red plaid skirts, white shirts, white stockings, and red high heels. I’m sure we were quite a sight. We each started touching Mark, and I felt him put an arm around my waist. Wow, was this really happening? It felt so good. I rubbed my hand across his chest, and the other went down and started feeling his ass. I looked over at his wife, and she seemed to really be enjoying this. She was already rubbing herself through her clothes. I could see Dawn on the other side of Mark doing the same as me. Suddenly he turned and kissed Dawn, and my cock got wet almost immediately under my panties.
I reached around front and started unbuttoning Mark’s shirt as he was kissing Dawn. There was something surreal about all this in the moment. This guy kissing my wife inches from me, and me dressed almost identical to my wife unbuttoning his shirt. But it was so hot too. Mark obviously liked this and turned and started kissing me.
This was the first time I had ever kissed a guy, but it still felt good. I have this habit of opening my eyes when I’m kissing, and as I did, I could tell my wife was turned on by this. She took over unbuttoning his shirt for me as Mark and I kissed even deeper and I felt his tongue searching all over my mouth. I couldn’t help myself and reached down to feel his cock. It seemed like such a natural thing to do, and his cock felt so hard in my hand through his pants. And I could tell it was going to be a pretty good sized cock as well. Mark moaned as I did it, and Dawn smiled at me approvingly.
Then I felt Dawn push Mark away just enough so we could each remove his shirt all the way. He was built fairly well. He wasn’t a body builder or anything, but Maria definitely was lucky to have a guy in good shape like this.
Speaking of Maria, I noticed she loved watching this part. She was unzipping her pants, and moaning the entire time, never taking her eyes off us. I leaned over and kissed his chest a little, then Dawn reached over to me, and we started kissing each other passionately right in front of Mark, and you could tell he loved every second of it. He reached in and squeezed both our breasts for a second while we were doing this.
Once we had Mark’s shirt off, Dawn and I got down on our knees in front of Mark. This was totally the moment we had fantasized about probably fifty times. Dawn let me unbutton his pants and she rubbed her hands up and down his legs and around back to his ass. Then I unzipped his pants, and pulled them down, the entire time thinking about how often I’d imagined this.
My cock was soaking wet by this. Mark had boxers on underneath, so I reached in and felt his cock in my hand.
It felt so good, and was so hard. I was a little nervous, but I pulled it out to see it, and it was a nice 7” or so. I could tell because it was just a little bigger than mine. Dawn put her hand on it too, and so there we were – both red heads on our knees in front of Mark with our hands on his cock, looking up at him.
He loved it, and I think at this moment to him it was two women down here. To Maria, she was having her moment of seeing her husband’s cock being stroked by two twins, and she was totally turned on by it.
Dawn and I stroked his cock for a few seconds, then she moved my hand away, and she said, “This is for you sweetie,” and she guided his cock towards my mouth. I took a little in at first, then she put her hand on my head and guided me like she said she would. First a little, then a little more, then suddenly Mark’s entire cock was all the way in my mouth as far as it would go. My first real cock, and it felt better in my mouth than I even thought it would. No wonder my wife enjoys this so much. It’s erotic, and like some sort of sexual power.
Dawn leaned over and whispered in my ear, “I love watching you do this to him sweetie. I want to enjoy all of this. Now, remember to look up at Mark, and then sometimes look over at Maria too. I just want to watch you from this point on sweetie.” God she is so hot, I am so lucky she is my wife.
Dawn continued to guide Mark’s cock for a minute, but then put my hand on it, and took hers off. So now here was my turn, all my turn. I slid right in front of Mark, and now it was like all those videos I had watched, and all those times watching Dawn do this to me, but now I was the girl. And it felt so sexy to be the girl on her knees in front of this guy, and I got as close as I could so he could feel my breasts against his legs.
I wondered what I looked like from his perspective, and if he enjoyed the view. From the sounds of it, he did. Dawn stood up and started kissing Mark, and I noticed that he even lifted her shirt up to see and feel her breasts. I loved watching this from down below, as I was still enjoying my first cock going in and out of my mouth. But seeing him do this to her too almost made me cum without even being touched.
“Hold on one second, Ashlynn, I have an idea,” Dawn said. And she sat Mark down on the couch. Dawn took her shirt all the way off. I love her breasts myself, so I know Mark probably loved them too.
I slid up in between Mark’s legs, and came to his cock that was standing straight up, as hard as it could possibly be. I knew he could feel my breasts pressing against him, as he moaned the second he felt them. I leaned over his cock, and immediately started bobbing up and down on it, going faster and faster.
Dawn had been kissing Mark, and then out of the corner of my eye, I noticed he had pulled down her bra, and was now sucking furiously on her breasts. This was totally turning me on as well, and I didn’t even realize at first I had slowed down a lot because I was watching this. I looked over at Maria next, and as I went up and down on Mark’s cock, I noticed her pants were totally off, and she was touching herself furiously, never taking her eyes off us.
Dawn was up on her knees, and had Mark’s faced buried in her breasts. I was really enjoying all of this, but had sort of lost focus watching everything else going on. Then all of a sudden I felt Mark’s hand on the back of my head, and I could tell he wanted me to go faster. So I went back to being in the moment, and began furiously sucking this delicious cock.
My hair was all in his lap, and I was looking up at him out of the corner of my eye. I could feel his cock starting to swell, and his was moaning more than ever, so I knew this was going to be it. His hand pressed harder on my head, and he was going wild on Dawn’s breasts with his face. She’s not normally big on this, but she was going wild with her breasts.
“Don’t stop, Ashlynn, I’m going to cum,” I heard Mark say, breaking away from Dawn’s breasts only long enough to get that out. Maria moaned loudly when he said that, and I could tell she was having a really great orgasm.
Hearing him say that turned me on so much, I could not wait for him to cum. I bobbed up and down, using my hand and my mouth now, and I could definitely taste some of his pre-cum. Suddenly, he pushed hard on the back of my head, and I heard him moan deeply first, then there it was, my first time, and my mouth was filled with his warm salty cum.
It tasted just like I thought, but I focused on swallowing every drop of it. I was almost done when suddenly Dawn was there, and she started kissing me deeply, and I gave her some of it too.
My first time definitely went different than I expected. I always imagined Dawn and I sharing the entire time together, but she literally had me do almost everything. It was amazing.
Mark pulled me up on the couch next to him and started kissing me, and feeling my breasts. I loved this part of it almost as much. I loved having my breasts rubbed, and his hands were all over me. Dawn went over and sat next to Maria and I actually saw Dawn kiss her – wow! Dawn must really be getting into this. I heard Dawn asked her how she liked it and I assumed that was going to be end of it as the two women would start talking about it now. I couldn’t hear what they were saying, but there were a lot of smiles and dirty looks.
Dawn stood up, and Maria called Mark over. As he stopped kissing me, he whispered in my ear, “That was amazing Ashlynn, I’d love for you to do that to me anytime,” and got up.
Wow, I mean could he have possibly said anything better to me? After fantasizing about this for so long, and always imagining it, but also worrying about how it might all go. That made my night. I stood up and was straightening everything up. I wasn’t exactly sure what happens after all this so I just sort of stood there. Dawn came over and kissed me and told me how turned on she was. I was thinking about as soon as they left what I’d do to her.
Then Dawn said, “Maria wants him to fuck us. Well actually she wants him to fuck you.”
What? As much as I had been thinking about everything that might happen, somehow I hadn’t really imagined that would be part of it, probably for a million reasons. Then I realized there still may be an out from this – Mark.
I turned around and looked at them talking. And it was clear he definitely was more than ok with it.
“Are you sure about this Dawn?” I asked, maybe hoping she’d say no, but yet still excited.
“Sure? Mmmm…I can’t wait to see this! And you’re going to lick me while he does you, so not only will I get to watch, but I’ll get to feel every time he goes in and out of you. So I can’t wait to get started,” Dawn said very excitedly.
Well, this night has not gone anything like I thought it would. And I love it.
To be continued
