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Filling in for GinaI had know Jay since I graduated from college. I met him when I started my first job. We were instant friends and hung out a lot. Our wives were friends until I got divorced. Jay and Gina, his wife, kind of helped me through it all. That was 10 years ago. Now Gina’s mom was sick and she was going there all the time, leaving Jay alone. I tried to go over as much as I could and every Sunday we would get together fans watch football. We had a fantasy league Jay ran, so it made sense to go there.What Jay and Gina didn’t know was my wife left me because she caught me dressing in her clothes. After she left I bought some of my own clothes and continued.Now to my story. It was late October, Jay and Gina were planning a Halloween thing. Gina insisted it was a party, more of a gathering. What’s the difference. Then I was over the Sunday before Halloween and Jay was trying to figure out what to do if Gina was at her mother’s. She said she be there, but he was sure she’d be with her mom and they’d have to cancel. Gina said no and I told him if she wasn’t there I’d help him out.Gina had to go and we watched the games together. Jay explained to me they already had there costumes and they kind of matched, so I couldn’t really fill in for Gina. I asked what he meant and he explained. They had planned on hosting the gathering and had purchased matching pirate costumes. Without Gina it wouldn’t be the same.Without thinking I said, “Well I can dress as a pirate if it helps.”“Oh I don’t know buddy. I’m not sure you understand.”“Oh come on. I’m sure I can be a pirate with no trouble.”Now maybe we were both a little drunk at the time, but he seemed to cheer up a little.“Well, the costumes kind of match… sort of.” He said.“Okay…”“I guess you’re kind of the same size as Gina.” He laughed.I was a little too drunk to put two and two together. “Yeah I guess I am.”“So you think you can wear her costume?” He suddenly got serious.“I guess I could.” I answered.“Buddy… I mean, it’s a girl pirate costume… you know, pirate’s wench.”I stopped and just stared at him, suddenly realizing what he was talking about.“Oh… I didn’t think… you know.”Now it was his turn to push me, “Come on… your right, you can help me out.” The smile on his face scared me.“No… I didn’t think. I mean about Gina’s costume. I can get my own.”“Not, it wouldn’t be the same… her costume or we’ll have to cancel the party.”We continued watching the game, I was getting nervous and excited. I so wanted to dress up for halloween. But this was too much. Jay was texting on his phone. Suddenly my phone buzzed and I looked at it. A text from Gina? She never texted me. “Jay told me you wanted to help us with the party. It would be so great if you could.”Looking at Jay, “You asshole. Why did you tell Gina.”“It’s her costume and wanted to make sure she didn’t mind you borrowing it.” He laughed.“Well, I’m not doing it.”“Oh come on. First it’s halloween, everyone dresses up. Second, I need your help… friend. And Gina said she’d help you with the outfit.”After a few more beers and a lot of pushing from Jay… and Gina, “Okay, let me see the costume.”Jay stood up,”now you’re talking, come on it’s in our bedroom.I followed him into his bedroom. He went into a huge closet and I looked inside. It was a big walk-in closet, full of Gina’s clothes and shoes.“Damn… she has a lot of stuff.”“Yeah, she has a bit of a clothes fetish. Oh here it is.” As he pulls it out and comes out, handing it to me.“Oh I don’t know. I mean a corset and stockings? And those boots. I mean look at those heels. I’ll never be able to walk in them.”“You’re right… what you need is practice.” Jay smiles as he goes into the closet. “Come on, pick out a pair to try.”I don’t know if it was the beer, or my desire, but I stepped into her closet and started to stare at all the shoes as Jay said, “Maybe kurtköy escort you should put on a skirt to. You know, to get use to it.”I looked at him and he almost seemed to be checking out my ass.“Yeah… maybe.” As I picked up a pair of heels and then sat them back down, only to pick up another pair. “Maybe these.”“Yeah, they’re sexy as hell… and about the same height.”“So you think a skirt too?” I asked.“For sure.” Jay answered. “And pantyhose or stockings.” He pulled open a drawer full of panties and another of lingerie and a third with stockings. “Sorry I don’t know much, but maybe we can find something in this mess.”I almost came in my pants as I look at all the lingerie Gina had. I was suddenly jealous.“Ah… yeah maybe.”Jay said, “You look around, I’ll grab us a few more beers. Try one anything you want.”When he came back with the beers I had picked out a few thing. A gartered corset, to give me a little shape and because the costume had one. Some stockings and a blouse and skirt. Seeing what I had he said, “put it one let’s see.”“Well, not with you watching… go downstairs and I’ll come down.”“Okay. Oh and Gina’s make-up and stuff are in the bathroom. Oh yeah…” he went into the closet and came out with a long brunette wig. “This came with the costume.” And he went down stairs.Once he left I stripped out of my clothes and started to dress… as Gina… for my friend. What the hell am I doing. Before I knew it I had the corset and stocking on. It felt so good. Her panty drawer was stuffed, but I quickly picked out a black thong and slipped it on. It matched the corset I told myself. Next came the make-up and wig and finally the skirt and blouse. I looked in the mirror and couldn’t believe how feminine I looked.Then I heard Jay, “Come on, what’s taking so long.”With a deep breath I walked down the stairs. As soon as he saw me he whistled and watch me.“Stop staring, walking in these shoes is hard enough.”“Sorry, but fuck, you look amazing.”Once I made it into the living room, he had me walk around a little and turn around so he could see me from all angles. As I turned back to face him, it looked like he had a hard-on.“Come here and sit by me on the couch.”From his voice it was not a request, but a command. One I eagerly obeyed.We sat and watched the game for a while. Then he said, “Why don’t you get me a beer.”I smiled and got up, walking slow in the extreme heels I had picked. Glancing back I saw him watching me. I got him a beer and returned, lean forward a little to hand it to him.“Thanks babe.”I sat down again. “So thanks babe?”“Oh sorry. But you have to admit, you look like a babe. What should I call you?”“Babe will do for now I guess.”“Good, so thanks babe.”At the next commercial break, “How about you fixing me a sandwich… babe.”I look at him for a few seconds and then ask, “What kind of sandwich would you like?”“There’s ham in the fridge babe.”I walk out to the kitchen and fix him a sandwich. I put it on a plate and take it in to him,“Need anything else… Honey?”With a smile, “No babe, I’m good for now.”We watch more of the game. At one point there is a shot of some cheerleaders. Without really looking at me, “You could be a cheerleader babe.”“What?”“You could be a cheerleader, you got the body for it.”“I could never do that.”“Well, I think you could… hey grab me a beer babe.”I stand up and Jay says, “Do a little cheerleader bounce for me babe.”I look back at you.“Oh come on babe, just a little for me. Show me how sexy you are.”I blame the beer, but I had stopped drinking when I got dressed. I stop up and did a little dance, trying to look like the cheerleaders. Then Jay moved to the edge of the couch and placed his hands on my hips… I froze. Then he started to push them side to side, “Come on babe, but a little more wiggle into it.”I did my best and he sat back and just maltepe escort stared. I looked down and saw his all to obvious bulge in his pants and strangely enough, I liked knowing I had done it.Finally I stopped, “Happy?”He glanced down at his crotch and gave it a squeeze, “Happy… for now babe.”This time when I sat back down he put his arm around my shoulder and pulled me closer to him… I was scared. Should I protest… tell him to stop? I was confused. I had been dressing alone for over a year now, hoping for the chance to do exactly this. But Jay is my best friend… and what about Gina.But as my mind is racing, my body is on cruise control as I feel myself wiggle in tighter against Jay, my head resting against him… is that my hand on his thigh… Looking down I saw my hand and a little higher up, his bulge. Could I? Should I? It was so close.“You okay babe?”Without even thinking, “Sure honey.”Well, at least for the moment we had pet names.Where was this all heading? Did we both want the same thing?I turned my head and looked up towards him, our eyes staring at each other as the game played on the TV. I seemed he was moving towards me, his face getting closer to mine as I felt his arm that was around me kind of pulled me. As me moved in slow motion, is he really going to kiss me? Do I want him to kiss me?And he does. Oh my, how do I feel about this. I’m not gay!He kisses me again. I’m so scared. I jerk back and look at him, “I… I… no… I can’t…” as I jump up and run as best I can in the heels up to his bedroom.I hear him behind me, “It’s okay. I’m sorry! I didn’t mean to!” He knocks on the door. “Please open the door. I think we need to talk about this. I shouldn’t have done that.”“Just leave me alone…”“No babe, we need to talk.”Babe? He’s still calling me babe.“Just go back downstairs… I’m okay. It’s just… well… just go downstairs I’ll be down.”“Come on babe!” He begs.After a few back and forths, he gives up and goes back downstairs, with my promise I’ll be okay and come back down. As I’m there, I can help but think I had fucked everything up by running away.Taking a deep breath, I check myself in the mirror. Then fix my lipstick. I unlock the door and step out. Okay I can do this. I walk down the stairs, a little surprised how good I’m getting in the heel. Practice does help. As I step into the living room, Jay looks up, a little surprised I’m still dressed like I am.“Are you okay?” He asks.“Yes honey, I’m fine.” As I move over and sit on the couch with him. “I was just a little surprised is all. I didn’t think you’d do that.”“I’m so sorry. I didn’t think.”I look at him, “It’s okay to call me babe. And it was okay… it was more than okay, and it scared the hell out of me.”“Well, it’s just you looked so sexy. I couldn’t help myself.” Then after a pause, “Babe.”“I don’t know about how sexy I look.“Trust me, you’re smoking hot.” Nervously I move forward and kiss him this time. There is an awkward pause before his hands touch me and he kisses me again. Then we are making out like long time lovers. He pushes me back on the couch as I feel him on top of me. This is what it feels like to be a woman… I like it. I feel so submissive as he manhandles me. Soon he is kissing my neck.“Your so sexy babe…”“Mmmm…” is my only response as you kiss me neck. I feel your hand on my waist as one of my legs drops off the couch. Then you move me, so you can get between my thighs. My feet drop to the floor as you pull my face to yours and shove your tongue in my mouth.We kind of break for a few seconds and your phone dings. It’s Gina. She wants to know if we found the costume.‘Yes, found everything. I think it is going to work out.’‘Oh that’s so good.’Then you toss your phone on the couch as kiss me again. As you break the kiss you stare at me. A little confused, I ask, “What? Is kartal escort everything okay?”You have this weird look on your face and it kind of scares me. Grabbing your phone you snap a few pictures of me, then say, “Gina never let’s me do anal.”Now I am scared, “And you think… me?”“Oh yeah babe… I’m thinking you. Come on your fucking gorgeous. And those legs are amazing. And it will help us appear more like a couple if we know each other better.”“Yeah, but I’m a…” and you stop me.“You’re a beautiful woman to me. And I want you.”I don’t know what to do… what to say. And while I’m trying to rationalize everything, I hear myself say, “Okay.”You quickly pull me up and spin me around, leaning me over the arm of the couch as you flip my skirt up. “Fuck babe, Gina’s ass never looked like that in those panties.” As you pull them down over my legs. I step out of them and then feel you lips on my ass. Kissing your way to my asshole. I’m ready to explode when your tongue lick my asshole. Then I feel something cold and look back to see you with a bottle of lotion smearing it around.“Need you nice and wet babe.”I can only moan, “Yes.”I can’t look back, I’m too scared. But I feel Jay moving and I feel his cock touch my ass.“Are you ready Babe…”“Yes…”I feel more pressure.“Are you okay Babe…”“Yes…”It hurts… a lot. But I know I could stop if I wanted to.Then more pressure and I feel the tip push in. He pauses. Then a little more.I moan as I push back. He knows I like it now and forces more inside me. Then pulling back, and forward again. After a few minutes I feel his body against mine and know he’s all the way in. “Oh honey, fuck me.”“You like that you little slut?”“Yes… more than I can say.”“I’m glad…” as he starts to slowly fuck me. “You’re my slut now.”“Yes.” I can’t believe how wonderful his cock feels inside me.“I own that ass.”“Yes…”“Every night Gina’s going you’re coming over and dressing in her clothes.”“Yes…”“And making me dinner… cleaning the house…”“Yes.”“And I’m going to fuck you every night.”“Yes.”Jay’s hands caress my body as his cock slides wonderfully in and out of my ass. I was being fucked like a woman, and I was loving it. The feeling was so amazing. “Ahmmmm…”“You like that slut?”“Oh yes… I do…”Then I felt his hand slap down on my ass. He had spanked me.“Fuck me back slut.”“Yesss…” as I started to rock back to meet his every thrust.“That’s a good girl.” As he slap my ass again.“Aghhh… mmmmm…”“You’re a good fuck babe.”“Oh yes…”“You like my cock don’t you.”“Mmmmm…”Tell me!” Slap“I like your cock!”“Tell me whose girl you are.”“Yours… I’m your girl.” I knew he was close… he was going to cum… inside me.“Fuck me…” I half begged. I needed his cum.With his hands firmly on my hips, pulling me hard against him, his cock erupted, spray his man cum into my tight little boi pussy. And I came. Without ever touching my cock I had come. As Jay calmed down, he eventually pulled his cock out of my ass. He spun me around and kiss me, forcing his tongue into my mouth. When he finally release me he looked into my eyes. “Your a good slut.”I could only smile and answer, “Yes.” Then as we moved a little he saw my cum on the couch.“What the fuck slut.”“Sorry… you fucked me until I came.”He laughed, “You slut… clean it up.”I started to go to the kitchen when he grabbed me, pulling me back, “With your tongue bitch.”I look at him and then lean over and lick my own cum off the cushion. When I finished he said, “That’s a good slut.” Then he tosses me Gina’s panties, “Put them on so my cum doesn’t drip everywhere.”He sits back down on the couch and pulls me down beside him. After a few kisses, “Tomorrow wear Gina’s panties to work. And you’ll need to show me. After work, you come straight here, get dressed and start making my dinner. I expect you to take good care of me.”“Anything you want Honey.”“That’s a good girl.”We watch some more TV and around 10 I was going to change to go home.“Why don’t you wear them home. You can bring them back tomorrow.”“No, I don’t think it’s a good idea.”He looked at me, “I insist.”Unsure what to do… “Okay… if you insist.”
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