Wearing buddies wife's clothes
My fantasy.
I was watching the game at my friend's place, and we were putting back drinks. Every time the cheerleaders came on, he kept saying, “Man, I haven't made love to my wife in forever. I'm going crazy.” Well, on a trip to the bathroom, I noticed a pile of laundry on the bed, and right on top was a bra. An idea popped into my head: I'll dress in his wife's clothes and tease him.
I snuck into the room and closed the door. After putting on the bra and panties, I realized I needed more. After some searching, I found the jackpot: a cute teddy, thigh highs, and a garter belt, a lacy shoulder shrug, and a pink wig. I got excited as I put all of it on, and I then found some high heels to complete the look.
I walked back into the living room, dimmed the lights, and in my most girly voice, said, “Glad to see your friend left. We have the place all to ourselves. What do you want to do?” He turned around so fast with the happiest look I’d ever seen on his face, only to fade it to complete sadness when he realized it was me. I couldn't even laugh. I immediately felt bad. I immediately told him, “I'm sorry. I thought it would be funny, but the look on your face makes me wish I hadn't done that.”
His eyes started watering. He said, “I remember that outfit. She wore it for me for my birthday. We had the best sex ever that night.”
I said, “I'm sorry. I'll go take it off.”
He said, “Wait, since you're already wearing it, could you just do me one favor? I have one more item you can wear with that.” He ran to his room and brought out some breast forms that he bought for his wife after her mastectomy in hopes it would make her feel better.
As soon as I saw them, I needed to know what it would feel like to wear them. As I was putting the corset back on, he said, “Let me help you with that.” He pulled it so tight I could barely breathe, but the hourglass figure started to appear. The breast forms were getting pushed up and squeezed together, and my hips started popping out, making my booty look huge in this mini skirt.
He asked if that was too tight, and even though I could barely breathe, I wanted to see how far it would go, so I told him to go tighter. At this point, I was getting excited, looking in the mirror, grabbing the fake breasts, and squeezing them together. I realized I couldn't pull my cock out because the thong was pulling back so tight it felt like it was tied in the back somehow. I started rubbing the smooth little hump that was trapped under the thong. I envisioned I had a pussy as I gropped my breasts and pinched the nipples. I was feeling some type of way.
I snapped out of it as my friend slapped my ass so hard my dick tingled. I don't know why, but I was dreaming about being at the bar dressed like this and guys buying me drinks. I turned to my friend and said, “You did always say I had a fat ass. How does it look in this skirt?” I realized he was grabbing his crotch like it was hurting him. I bent over, and he came up behind me, pulling me tight to him as I felt his huge bulge.
I pulled away. “Damn dude, I didn't know you were packing that!” I was excited that I was the reason for that erection. He then asked if I wanted to see it. I was curious and said sure. As soon as it popped out, I uncontrollably licked my lips. My friend noticed and smirked, asking me if I wanted to touch it. As much as I did, I snapped out of it, saying, “No dude, I'm not gay. You obviously are though, getting a boner from a man.” At that point, I had to prove I wasn't gay and said, “Okay, I’mma take all this stuff off now.”
Then he said, “Wait, one more favor since you started this cruel joke. Can we spoon on the bed for a little bit?”
I resisted for a little bit but then realized I wasn't ready to take off this lingerie. It felt so good and was sending a rush all over my body. So I said, “I feel bad for tricking you, but you need to leave your clothes on and put that thing away.” He smirked and agreed.
I crawled up onto the bed and as I did, looking in the mirror, I bent forward, sticking my ass as far as I could in the air. Then I lay on the bed with my back to him. He crawled in behind me and cupped my breast. I was waiting to feel his bulged, pressed up against me, but it never came. Suddenly, I felt empty. I wanted to feel it again. I scooted back until I felt him. He laughed, “Yep, it's still there.”
As we lay there, I felt him with his hand by his crotch. I assumed he was just pushing it to the side until I felt it poking at my thigh gap. I said, “Hey! What are you doing? I said keep your clothes on!” Secretly I wasn't mad though.
He said, “Just let me rest it there. It was uncomfortable tucked in my pants.” Then he spat in his hand and rubbed it on his cock and slid it between my thighs. It was so long the head was sticking out the other side.
I instinctively grabbed it and said, “Wow, dude, if I had your cock, I probably wouldn't have been cheated on in my last 2 relationships.” I moved it next to my crotch, hoping he wouldn't notice what I was doing.
He chuckled and said, “Thank you, this is nice.”
I said, “Well, the look on your face made me feel bad, so I hope this helps.” Next thing I know, he's humping my thighs. I didn't say anything at first, but then the friction was getting annoying, so I said, “That can't feel good for you. It doesn't feel good for me.”
He said, “You’re right, but this thing just won't go away. Can I ask one more favor? There's something I want to try that I can't do with my wife after her mastectomy. Can I tittie fuck you?” I was excited; I wanted to see that nice cock fuck these perfect tits like I was up close at an actual porn shoot. He pulled me to the edge of the bed, with my head hanging over the side, and pulled out so lube from the nightstand. He started tittie fucking me. I was squeezing them together, like the girls do in porn, getting excited for the cum shot that he would leave on these titties.
All of a sudden, he stopped. I was disappointed and asked, “Are you done?” He said it was starting to hurt.
“I need more lube, but the tube is empty. Can you spit on it?” I did, and he said, “That’s not working.” I looked up and saw he was filming me.
I asked, “What are you doing?”
He said, “I needed some incentive for what I'm going to ask next,” as he flipped the phone showing a group chat with my family with the video attachment and his finger hovering over the send button.
“You started this. Now you gotta finish it. Open your mouth.” I saw evil in his eyes. I tried to get up but realized I couldn't move with how tight the corset was tied. “Don’t test me. Open your mouth.” So I did. I was gagging instantly. I had both my hands on his shaft, trying to keep him from pushing it further down.
He grabbed my wrist and moved my hands to my breast. “No hands. I want you to play with your breast.” He started to force himself down my throat as it opened up. I thought I was going to pass out. He grabbed my hand and moved it to my neck. He said, “Feel that? It’s in your throat.” I started squirming. I felt weak. He finally pulled out, and I was able to breathe again; but that relief ended quickly as he was pushing himself back into my throat over and over again. I reached up out of curiosity and felt my neck. Wow, I could actually feel it.
Finally, he pulled away and twisted me back on the bed. I was exhausted and gasping for air. I turned away from him, and next thing I know, he's on the bed, straddling me, flipping me on my stomach. He ripped the pantyhose open, and I felt his cock pressing against my butt hole. He said, “This will be easier if you rub some spit on it.” My face is covered in it, so I wipe my face and slide the saliva down my butt crack. He said, “I'm sorry for earlier. I'll go slower here. I don't want to hurt you.”
I don't know why, but I said thank you. Now, mind you, this isn't the first time I had something in my butt. I had a girlfriend who would peg me anytime I got whiskey-dicked as punishment. When he realized how easily it slid in, he laughed and said, “This isn't your first time, is it?” I told him Sarah and I used to explore. “Ever had anything this big?” I told him no, but I was curious if I could take it all. “I should warn you, I can make it to the first bend, but I've never had a girl get past that point. Here, I'll show you.” I felt it, it hurt, I pulled away. “Yep, there it is. I still got a couple more inches if you want to try.”
I reached back, pulled his cock out, and asked if I was bleeding. I immediately felt an emptiness and was desperate to get him back in me. I asked if he was close to finishing. He said, “I don't see any blood, and I'm so close. If you haven't stopped me, I would have already finished.”
I said, “Okay, let's get this over with.” When he was back in, I didn't want it to end and was sad that he was almost finished. I said, “Hey, wait, can you take a video and show me what it looks like?” He did, and I saw there were still a few inches, and now it turned into a challenge. I've seen girls go deeper, why can’t I? Plus, I want to feel him slap my cheeks as he was all the way in. “I want to try and take it all. Just go slow.” He was rock hard at this point, and it got me excited knowing I was the reason for this.
So he slowly starts pushing it. It could feel it creeping in more. I tried to relax as much as I could. This feeling was insane. I felt like I was going to explode. I wanted to rub my stomach to see if I could feel it, but I was wearing the corset. He asked if it was okay and said he's never been this deep in anyone. I said, “This is an intense feeling.” He said he didn’t want to push any further and told me to push back if I wanted more. I said, “Try going in and out a couple of times.” Each time he did, his cock hit that curve, and it hurt but felt like it was getting easier. I told him to stop, and I closed my eyes and grabbed handfuls of the bed sheets and pushed back. I felt it go deeper. I said, “Just do it, push it all the way in. I have to know.” He pulled back a little and thrust all the way. It hurt, and I tried to pull away, but I couldn't go anywhere. I was flat on my stomach, and he was laid out on top of me. He stayed in me and told me to relax and not to clench.
He said, “You did it.”
When I came back to reality, I realized my ass cheeks were being smooshed by his thighs, and he was all the way in me. “Now relax. I'm going to pull out a little and go back.” I told him to take another video. I wanted to see. While he was videotaping, I pulled my ass cheeks apart.
I lay there watching the video as he went back and forth a couple more times. It was getting easier now. I said, “Okay, I think I'm good. Can you go faster?”
He said, “If I do that, I'm going to cum soon. Where do you want me to finish?” I told him I want him to cum as deep as he could in my ass. He went hard for about another 5 minutes. I could feel his cock get even harder, and I knew he was about to cum. I pushed back as hard as I could. He grabbed my hips and pulled me close and erupted inside me. I felt completely full as shot after shot of his cum painted my insides. As he pulled out, I handed him the phone and told him to video the cum dripping out of my ass.
Now it was my turn. I climbed on top of him and started throating his cock clean. He said he was too sensitive and was begging me to stop as he tried pulling me off of him. I said, “There, there's a little payback” with a cocky smile on my face as I wiped his cum with my finger and liked it clean. My smile faded when he reminded me who had the videos.