Playtime Stories 17 BBC Afternoon Delight
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Playtime Stories Ch 5 - Best Leather Sales Lady Ev free porn video
5.
Shopping is not one of my favorite things to do. I still want to get there, find the items, buy them, and leave for home or wherever and use the items. However, I am female enough that I always want to have instant gratification and see how the item really looks on me.
A couple of years ago I had just begun to buy good quality “stuff” for my little whore-adventures. I was always awkward doing this because it is kind of embarrassing to buy erotic women’s clothing as a guy when it is plainly obvious that it’s your size. I also noticed that sales people are usually aware of my true motivations. I’ve tried saying it was for a fictional girlfriend or a Halloween party, or a costume party, or the lame but strangely believable “I lost a bet.” Actually, the “I lost a bet” really worked out for me a couple of times.
I was in town on business. I’d finished early and I wanted to get something special for that night. When I scheduled the meetings on my trip I had made sure I would have at least one or two days open and I was determined to make the most of them.
So here I was at a leather apparel shop at the mall about 10 minutes away from my Motel. I was really excited about my “new look” and was meticulously putting it together with nice things, not mix-match stuff from a second hand store. I finally had the means to create the look that I wanted. I wanted hot and I wanted black – just like my favorite variety of cock... I wanted a BDSM-meets-slutty look. I wanted tough black leather.
I already had a hot looking and somewhat functional leather harness, that I still love, and a really hot waist cincher with six double-attachment garters, but I needed more to complete the look. After all, a good gurl has to get from her ride to the theater, or arcade, or motel, or well wherever she is going to be a whore in somewhat normal and ‘legal’ clothes.
I came in the leather store with my other purchase in the mall- a wonderful black lingerie set – bra, panties, and thigh-high black stockings. Maybe that bag is why everything “fell” into place this time.
I came into the store at about two PM and browsed. The fact that I wanted leather didn’t mean I would find what I wanted, I am choosy. Shortly after I got there the guy who worked there, who was about 25 and way too gay for even my tastes, walked up and asked if I needed any assistance. When I’m buying whore stuff for myself dressed as a guy I am always very uneasy dealing with a guy, so I politely said no and continued looking.
A short while later his associate returned from lunch. She was a nice looking middle-aged brunette who looked good wearing the store’s leather wares. She wore a smooth knee-length dark purple skirt that accented her nice ass and a loose white silk blouse with full sleeves and Nude pantyhose with black pumps. She was in her late 30’s and had a naturally pretty face with brown eyes accented by slightly heavy mascara and shadow. When I saw her I thought she had a wild side. About five minutes passed and they spoke casually about the mall and other stuff.
I found a couple of skirts and a belt, but no top. I was quietly shopping.
The guy left for lunch as another customer came in to get a refund for a birthday present. The sales woman paid her the refund and then noticed me still shopping in the ladies section.
“Are you looking for a gift?” she inquired.
I lied, “Yes, ah, actually, I am looking for some stuff for my sister. She wants something nice for her birthday.”
“Well, what kind of things are you looking for?” she asked.
“Well, she’s all grown up so I want to get her something that shows that I know that. I’d like to get her something a little racy.”
“I see. Have you considered a gift certificate? The only reason I ask is because some of the clothes have here should really be fitted by the person who will wear them.”
I was slightly mortified. How do I dodge that? “Well, even if she has to exchange it I want her to receive something she can have and hold on her birthday.”
“Oh, yes, I completely understand, but we could put a nice gift certificate and card in one of our gift boxes and maybe throw in some gloves.” She persisted.
I was still looking at the skirt I wanted. I was becoming a little annoyed with her and said, “I really think this skirt will work out.”
At that point the sales lady, her nameplate said Gail, walked to the skirt I was looking at and saw it was a large. “What is your sister’s waist size? This is a large. If you’re not careful you may make her think that you think she’s fat!” She said with a chuckle.
I really wanted to get the hell out of there at that point. “She’s about a 34 or 36 inch waist, and about 5’6”, I think.”
“Oh, so she’s roughly about your size? That’s handy.” She said that turning toward the skirt with the type of look and smile of someone who’s just busted me.
I leveled with her to get the skirt with the least amount of problems. “Ok, actually she’s exactly my size because I lost a dumb bet and have to go to a costume party wearing women’s clothes.”
She looked at me and said “Ok, well this stuff might be a little nice to buy for just one party, let’s see what we have on our clearance rack.” She turned and I followed.
She had a point; I hadn’t found the clearance rack and hoped it would have something I could use. A few minutes later we had found a longer skirt and a nice sleeveless vest with a zipper, large.
“Well, I guess the skirt is not as nice as the other one, but I think the vest will work well. Do you want to try them on?”
I was almost speechless. “Well, do you think it is necessary?”
“Believe me, you don’t want to come back and exchange these if they don’t fit. Go on, it’s ok.” Then she guided me to the dressing room. Then she saw the lingerie bag and said, “Must have been a good bet to loose, those look great. I am sure you will have a lot of fun!” she said smiling, as she closed the door.
The room was slightly larger than most. I was hard and had pre-cum all over the end of my cock. I went ahead and undressed, stroking myself more than a few times. I dismissed the idea of jacking off in the booth and proceeded to dress.
As I was zipping the rear of the skirt I heard her complete a sale and bid them to return.
As I checked the fit in the mirror and adjusted my hard cock to stand straight up front of the skirt in I paused and admired my perfect ass. A million nasty fantasies rushed forth. I imagined pulling it up for strange men to fuck me and cum stains all over it…
“How does it look?”
That seemed weird. She was a little too attentive. “Well, so far so good,” was all I could say.
“Let me know if there is anything you need, ok?”
“Ok.”
Then I tried on the vest. It was too small. If it had been the right size, the story would never have been told.
I momentarily wrestled with the vest and then heard a knock.
“How’s the fit on the vest? I think we have an extra large that might work better”
I said, “Well, I think that might fit better. Would you mind?”
“No problem, that’s my job. I have it here.”
The dressing room was a little too private. Unlike most dressing rooms, the door was full length and had a very narrow gap at the top. I was going to have to open the door.
Well, I said to myself, who cares, she knows the stuff is for me, I don’t even live in the area. I said to her, “Ok can you hand it to me?”
“Sure.”
I opened the door and saw her standing there in position to look beyond me and my peering head to see the mirrors in the booth.
“Well, the skirt seems to fit very nicely.”
I started to get a surge in my crotch. “Yes I like it, thank you.”
“Can I see it?”
“Well, uh ok.” I stepped out from behind the door and stood in front of her naked except for the skirt.
She quickly looked at me and than shifted to the mirrors, checking me out and then looked down at the impression my hard cock was making on the front of the skirt. “Wow! Uhhm, that looks, ah great. Yeah, great. You better be careful at the party with that on.” She said with a naughty smile while holding the vest out to me.
I took the vest and said, “Yeah, I’m expecting that.”
“Are you? Well that would be a fun party.” She gazed at me for a moment and then said, “Well, put on the vest, and let me see after I help this customer.”
I closed the door and put the vest on. It fit nearly perfect. The sides had a little elastic and made it comfortable but snug and well formed. My mind wandered and I imagined how hot it would look with the bra and harness visible between the “V” of the vest’s neckline. I felt my crotch strain against the leather.
She closed the register and returned. “Well? Does it fit?”
I knew I was getting harder but thought it might pass. I said, “Yeah, it fits well.”
“Well, could I have a look?”
“Sure” I said not caring about my cock’s hardness and her shock. I opened the door to see her eagerly looking in at me.
“Wow! That looks great too.” She paused and tilted her head a little to her left, considering me. “You know, you’re fortunate to have a nice enough body for this thing, I mean, this ah, bet.”
“Well, I guess so.” My cock was swelling and I desperately wanted to be done shopping and get dressed and then go fuck someone.
“You know, sometimes we have guys come in here to get stuff for themselves to use in shows, you know, Drag shows. But you have one of the best fits I’ve seen.” She looked me up and down. “And you have nice legs too, how lucky. Your friends are going to be impressed. Are you going to complete the look with the lingerie?”
“Yes, well I ah, I lost a pretty big bet.”
“Really, sounds like a pretty wild situation.” Then there was a pause. “I’m sorry, I don’t usually pry so much, I guess I am just fascinated,” she said looking up at me.
“Oh you’ve been very helpful, I really appreciate it.”
“Well, do you need anything else?”
My mind wandered into the gutter and then returned. “I think this will do it.”
“Ok, well I’ll be ready at the counter.” She turned and walked.
I closed the door most of the way and reached under my new skirt and grabbed my cock and jacked it a few times. I was extremely turned on now. I admired myself in the mirror and wished she would come join me. The moment passed and I changed to my boring guy clothes. Five minutes later I was paying at the counter and she was a little flustered.
“Ok, $135.89, too bad the skirt wasn’t on the clearance rack, but the vest usually goes for $150 on its own,” she said with a smile.
As I opened my wallet, she noted my driver’s license.
“Are you here on business dear?” she asked.
“Yes.”
“Too bad about the bet, I hope it doesn’t spoil a good time.” She said with a coy tone.
I looked at her, my confidence renewed. “Oh it’s not going to spoil anything. Actually, it will be a lot of fun.”
“Is this the first time you’ve had to cross-dress?”
There it was. Nowhere to go. I quickly decided to play along and see where it went. “No, actually it isn’t. I’ve done it a few times.”
“Always for bets?”
“Well, actually no.”
“Really? It must be kind of difficult to need to do that during a business trip away from home.”
“Well, it actually is easier in some ways; I probably won’t run into anyone I went to school with or anything like that.”
“Yes, I suppose so.” She paused. “I have a question, how far do you go for this look? I mean do you have to really look the part or are you just supposed to wear the clothes?”
“Oh, I need to look feminine. It’s all part of the deal.”
“Well it sounds like an exciting get-together.” She said leaning forward and resting on her elbows.
“We’ll see. I think it will be.” I handed her cash with a little laugh and obviously leering at her white bra straining against her cleavage.
She reciprocated the laugh and bagged the items. She held up the bag and asked, “Is the party open to anyone, I would love to see the final product.”
“Well, it is actually a private function, but maybe, if you wanted, you could, ah come by and ah, see me before I go…if you want.” I offered, totally throwing the ball in her court.
She looked over at a couple of teen girls who entered the store. “Well, I don’t know. What time will you be ready?”
“The party begins about seven-ish. I’ll probably be ready around five-thirty or so.”
“Oh, I don’t know. I get off at three thirty and have to pick up my k**s at six. I would love to stop by for a few minutes and see how you look. How about I come by about four-ish? Maybe I could maybe give you some assistance.”
“Sounds great…I’m staying at…”
About three I started getting ready. I was so excited. What kind of freak had I met? What kind of freak did she think I was? What would happen? I was so hard. I was ready about three thirty. I watched porn and fought the desire to jack off. I positioned a Tranny magazine, lube, condoms, and a dildo in plain sight.
At 3:40 she called me and asked if she should still come by. I told her I was ready and the party had been moved up. I said she should come over right now because I had a question for her. At 3:50 I heard high heels walk to my door and then she knocked.
I walked in my heels and hot new clothes to the door and opened it and stood back away from the threshold.
Gail came into my room wearing her own short black skirt herself and carrying a bag from the store. She was wearing a darker lip color than earlier and her eyes seemed darker.
She looked me over and said, “Wow, Holy shit you look great!” she exclaimed. “I love your shoes and the vest…” She paused and covered her mouth in surprise and astonishment, “Oh my, you have done this before, quite a few times.”
I turned around so she could see every side of my body.
“Wow...all I can say is wow.” She set her bag on the dresser and leaned against it and starred at me.
I beamed and continued making little poses. I kept watching her eyes feast upon me. She was definitely a freak of some kind, like me.
“This can’t all be for a bet. Why did you put so much work into it?” she searched.
In my slutty voice I came clean and said “This is all for recreation and fantasy.”
“Oh my god, you even sound great too, holy shit!”
I looked at her in her eyes and she held my gaze. She looked past me to see the toy and lube. I watched as she connected all the dots.
I broke her stunned silence with, “So, what’s in the bag?”
“My other skirt and some stuff I bought on break.” She changed the subject. “You look really good. How long have you been doing this?”
“For a long time.”
“Are you gay?” she asked.
I smiled wickedly as I stepped forward and closed on her and said, “I’m extremely Bi-sex-u-al.” I said licking my lips and looking into her. I closed in even further and looked down her blouse. I reached up and held her firm arms and kept coming in to a kiss. She didn’t resist. Our lips met and my tongue probed her, tasting mint and feeling warm wetness. Her lips were smooth and supple. She felt good. I raised her arms to allow her to grab my leather-clad ass. She was timid at first and then gradually increased the force of her grip. She moved her hands around and fondled my leather clad ass.
I lowered my grasp down her back and squeezed her ass. I stepped between her knees with my stocking clad leg and rubbed against her inner thighs. I reached down and touched the tops of her thighs and began pulling her skirt upward. I enjoyed the feeling of her hot skin beneath her pantyhose.
She broke the kiss. “This is crazy, I…Ah, um...ah have something you might like. Let me go into the bathroom for a minute and show you, ok?”
“Ok,” I said.
She looked up at me and rubbed her hand on my bulge. She smiled and said “Oh my, I thought I saw something earlier. I’ll be right back.”
She took her bag into the bathroom and closed the door. A few minutes later she opened the bathroom door wearing a set of matching red stretch-satin basics. She wore a brand new bra, garter, and panties and she had replaced her pantyhose with black fishnet stockings. She looked hot too.
“How do you like it?”
“I Love it,” I said walking to the bathroom doorway to feel her satin cased breasts. Her body was warm and toned.
She beamed with pride and looked at my dark mascara-and-shadow covered eyes.
I said in my wanton voice. “Would you like me to lick you till you cum in my mouth?”
“Oh my god,” she answered with the slightest of nods.
I slid my hands around her nipples and squeezed them through her red satin bra cups. She squealed a bit. I dropped down and knelt. Then I shifted her panties out of the way and opened her labia.
I met her gaze and breathed her in. She smelled like sweetly mixed body spray and cunt. I put my mouth against her sex and darted my tongue into her. She moaned as I softly licked her in little circles. Gail leaned back into the sink and looked down to watch me. I looked up at her with her sex in my mouth. I licked her and watched her focus on the show. She was sopping wet already. She held herself up by resting her hand on the back of the counter. She propped one leg up on the rim of the toilet. Sooner than I was expecting, her eyes rolled back and she began to cum. She made an ecstasy scowl and began throbbing and moaning.
I reached down and freed my cock and stroked myself. I had a condom in my thigh highs just in case. She seemed to enjoy cumming in my mouth as much as I did.
I ate her out and stroked my stiff seven and three quarters inch cock so hard that I almost came. I took my other hand away from her cunt and stroked her slit and teased her a little. She came down from her orgasm and looked down at me. She smiled and grabbed my hand from her cunt and pulled it up to her tit. She eased my other hand up to her other tit. I massaged and caressed her soft and shapely mature tits. I pushed the bra up and away from her nipples and squeezed. Her tits were very nice, not huge, and not too soft. Her nipples betrayed the fact that she had breast-fed at some point. I squeezed the nipples and sent shocks through her.
She picked my hands up from her tits and beckoned me to stand and follow her to the bed. She had me turn and lay down. I eased myself against the pillows and watched her go down on me with precision and skill. She was a very talented cocksucker. I watched her love my hard cock, protruding from the side of my panties. I noticed her reaching down to work her sweet wet pussy.
This is hot, I thought to my self. I met this talented woman who needs cock and is a little freaky at a store where I was buying slutwear, and now she’s her sucking my dick.
She had her fill of cocksucking and then rose up off me. She looked down at my thigh-highs and fished out the condom. Straddling my thighs and looking at me, she opened it and unrolled it down my stiffness. She grasped the base and guided herself down on it. She leaned forward and pushed her partially covered tits into my face as she began to fuck me with a rhythmic grind. I reached up and held her tits with one hand and with the other I reached back to her ass to grasp her garter covered cheek. I could feel her panties rubbing against my shaft and reached further back to pull them hard and shift them away from my cock. She felt the pressure of the panties shifting and then I realized I’d increased of pressure against her clit. She ground into me and then began to cum again.
We switched positions several times and ultimately she was on her back with her thighs raising her hips and ass off the bed. She rubbed herself as I fucked her. She came several times and was moaning loud.
Then, between an orgasm, she pleaded for me to “Put a thumb in my ass and fuck me hard!” So I did. I reached back and cupped her asscheek in my hand and pushed a thumb up into her wet pussy while I fucked her. Then I brought it back to her backdoor and shoved it with great ease. She came instantly and was moving so wildly that I could hold out no longer.
I pushed my cock into her and came hard. I filled the reservoir tip and the whole head of the condom with the semen she’d earned. Her orgasm continued through mine and she eventually lowered her hips downward onto the bed.
I was hoping for another fuck session, but she’d gotten hers and rolled off the bed and immediately began to dress.
I was still dressed, so I watched her as I peeled the heavy full condom off. I decided to make some small talk. “That was fantastic, I am really glad I went to the store today.” I joked with her, but she seemed to be a little uneasy. “Are you ok?”
“Sure, I feel great, I just haven’t cum like that in a long time. That felt great, you are so hot.” With that she smiled at me briefly.
“I hope you are ok. If there’s a problem, I’m sorry.”
She paused her dressing and looked at me. “No baby, there are no problems, I just, well, I just haven’t done this for a long time and I came really hard, that’s all. I’m a little light headed and running late and I need to go. I hope you understand.”
“Oh, ok. I understand. I really enjoyed you. I am glad you enjoyed this with me.”
She merely smiled and went to the bathroom to fix her hair. She came out after touching up her makeup and looking more presentable.
“Gail, I would really like to play with you again. I’ll be here in the afternoons and evenings for the next few days. Please call if you would like to play together. Bring a friend if you want.” I offered.
She looked at me and smiled and said, “I had a wonderful time with you. You are very talented and incredibly sexy. Take care, dear.” Then she proceeded to kiss me and walk to the door. Then she turned abruptly and wrote her cell number on the motel scratch pad. She turned and hugged me briefly. Then she saw herself to the door.
I closed the door and watched her go to her car and drive off. She never told me what the sudden change of attitude was. Was she married? Was she a lesbian who needed cock and felt bad about her mate? Hmmm.
Oh well, who the hell cares, I was feeling too good to be concerned about any of her issues. My cock was semi-rigid and it knew this was only a prelude to the night’s affairs.
Two days later Gail came by for a bootycall at three am. I had just returned from the adult theater where I had taken on well over twenty hot ass-fucks and blow jobs. She and I fucked and I told her about my time at the theater.
She stayed for a sloppy second helping and confessed that she had really been questioning her sexuality after our first time. Apparently, I’d caused a craving.
Shopping is not one of my favorite things to do. I still want to get there, find the items, buy them, and leave for home or wherever and use the items. However, I am female enough that I always want to have instant gratification and see how the item really looks on me.
A couple of years ago I had just begun to buy good quality “stuff” for my little whore-adventures. I was always awkward doing this because it is kind of embarrassing to buy erotic women’s clothing as a guy when it is plainly obvious that it’s your size. I also noticed that sales people are usually aware of my true motivations. I’ve tried saying it was for a fictional girlfriend or a Halloween party, or a costume party, or the lame but strangely believable “I lost a bet.” Actually, the “I lost a bet” really worked out for me a couple of times.
I was in town on business. I’d finished early and I wanted to get something special for that night. When I scheduled the meetings on my trip I had made sure I would have at least one or two days open and I was determined to make the most of them.
So here I was at a leather apparel shop at the mall about 10 minutes away from my Motel. I was really excited about my “new look” and was meticulously putting it together with nice things, not mix-match stuff from a second hand store. I finally had the means to create the look that I wanted. I wanted hot and I wanted black – just like my favorite variety of cock... I wanted a BDSM-meets-slutty look. I wanted tough black leather.
I already had a hot looking and somewhat functional leather harness, that I still love, and a really hot waist cincher with six double-attachment garters, but I needed more to complete the look. After all, a good gurl has to get from her ride to the theater, or arcade, or motel, or well wherever she is going to be a whore in somewhat normal and ‘legal’ clothes.
I came in the leather store with my other purchase in the mall- a wonderful black lingerie set – bra, panties, and thigh-high black stockings. Maybe that bag is why everything “fell” into place this time.
I came into the store at about two PM and browsed. The fact that I wanted leather didn’t mean I would find what I wanted, I am choosy. Shortly after I got there the guy who worked there, who was about 25 and way too gay for even my tastes, walked up and asked if I needed any assistance. When I’m buying whore stuff for myself dressed as a guy I am always very uneasy dealing with a guy, so I politely said no and continued looking.
A short while later his associate returned from lunch. She was a nice looking middle-aged brunette who looked good wearing the store’s leather wares. She wore a smooth knee-length dark purple skirt that accented her nice ass and a loose white silk blouse with full sleeves and Nude pantyhose with black pumps. She was in her late 30’s and had a naturally pretty face with brown eyes accented by slightly heavy mascara and shadow. When I saw her I thought she had a wild side. About five minutes passed and they spoke casually about the mall and other stuff.
I found a couple of skirts and a belt, but no top. I was quietly shopping.
The guy left for lunch as another customer came in to get a refund for a birthday present. The sales woman paid her the refund and then noticed me still shopping in the ladies section.
“Are you looking for a gift?” she inquired.
I lied, “Yes, ah, actually, I am looking for some stuff for my sister. She wants something nice for her birthday.”
“Well, what kind of things are you looking for?” she asked.
“Well, she’s all grown up so I want to get her something that shows that I know that. I’d like to get her something a little racy.”
“I see. Have you considered a gift certificate? The only reason I ask is because some of the clothes have here should really be fitted by the person who will wear them.”
I was slightly mortified. How do I dodge that? “Well, even if she has to exchange it I want her to receive something she can have and hold on her birthday.”
“Oh, yes, I completely understand, but we could put a nice gift certificate and card in one of our gift boxes and maybe throw in some gloves.” She persisted.
I was still looking at the skirt I wanted. I was becoming a little annoyed with her and said, “I really think this skirt will work out.”
At that point the sales lady, her nameplate said Gail, walked to the skirt I was looking at and saw it was a large. “What is your sister’s waist size? This is a large. If you’re not careful you may make her think that you think she’s fat!” She said with a chuckle.
I really wanted to get the hell out of there at that point. “She’s about a 34 or 36 inch waist, and about 5’6”, I think.”
“Oh, so she’s roughly about your size? That’s handy.” She said that turning toward the skirt with the type of look and smile of someone who’s just busted me.
I leveled with her to get the skirt with the least amount of problems. “Ok, actually she’s exactly my size because I lost a dumb bet and have to go to a costume party wearing women’s clothes.”
She looked at me and said “Ok, well this stuff might be a little nice to buy for just one party, let’s see what we have on our clearance rack.” She turned and I followed.
She had a point; I hadn’t found the clearance rack and hoped it would have something I could use. A few minutes later we had found a longer skirt and a nice sleeveless vest with a zipper, large.
“Well, I guess the skirt is not as nice as the other one, but I think the vest will work well. Do you want to try them on?”
I was almost speechless. “Well, do you think it is necessary?”
“Believe me, you don’t want to come back and exchange these if they don’t fit. Go on, it’s ok.” Then she guided me to the dressing room. Then she saw the lingerie bag and said, “Must have been a good bet to loose, those look great. I am sure you will have a lot of fun!” she said smiling, as she closed the door.
The room was slightly larger than most. I was hard and had pre-cum all over the end of my cock. I went ahead and undressed, stroking myself more than a few times. I dismissed the idea of jacking off in the booth and proceeded to dress.
As I was zipping the rear of the skirt I heard her complete a sale and bid them to return.
As I checked the fit in the mirror and adjusted my hard cock to stand straight up front of the skirt in I paused and admired my perfect ass. A million nasty fantasies rushed forth. I imagined pulling it up for strange men to fuck me and cum stains all over it…
“How does it look?”
That seemed weird. She was a little too attentive. “Well, so far so good,” was all I could say.
“Let me know if there is anything you need, ok?”
“Ok.”
Then I tried on the vest. It was too small. If it had been the right size, the story would never have been told.
I momentarily wrestled with the vest and then heard a knock.
“How’s the fit on the vest? I think we have an extra large that might work better”
I said, “Well, I think that might fit better. Would you mind?”
“No problem, that’s my job. I have it here.”
The dressing room was a little too private. Unlike most dressing rooms, the door was full length and had a very narrow gap at the top. I was going to have to open the door.
Well, I said to myself, who cares, she knows the stuff is for me, I don’t even live in the area. I said to her, “Ok can you hand it to me?”
“Sure.”
I opened the door and saw her standing there in position to look beyond me and my peering head to see the mirrors in the booth.
“Well, the skirt seems to fit very nicely.”
I started to get a surge in my crotch. “Yes I like it, thank you.”
“Can I see it?”
“Well, uh ok.” I stepped out from behind the door and stood in front of her naked except for the skirt.
She quickly looked at me and than shifted to the mirrors, checking me out and then looked down at the impression my hard cock was making on the front of the skirt. “Wow! Uhhm, that looks, ah great. Yeah, great. You better be careful at the party with that on.” She said with a naughty smile while holding the vest out to me.
I took the vest and said, “Yeah, I’m expecting that.”
“Are you? Well that would be a fun party.” She gazed at me for a moment and then said, “Well, put on the vest, and let me see after I help this customer.”
I closed the door and put the vest on. It fit nearly perfect. The sides had a little elastic and made it comfortable but snug and well formed. My mind wandered and I imagined how hot it would look with the bra and harness visible between the “V” of the vest’s neckline. I felt my crotch strain against the leather.
She closed the register and returned. “Well? Does it fit?”
I knew I was getting harder but thought it might pass. I said, “Yeah, it fits well.”
“Well, could I have a look?”
“Sure” I said not caring about my cock’s hardness and her shock. I opened the door to see her eagerly looking in at me.
“Wow! That looks great too.” She paused and tilted her head a little to her left, considering me. “You know, you’re fortunate to have a nice enough body for this thing, I mean, this ah, bet.”
“Well, I guess so.” My cock was swelling and I desperately wanted to be done shopping and get dressed and then go fuck someone.
“You know, sometimes we have guys come in here to get stuff for themselves to use in shows, you know, Drag shows. But you have one of the best fits I’ve seen.” She looked me up and down. “And you have nice legs too, how lucky. Your friends are going to be impressed. Are you going to complete the look with the lingerie?”
“Yes, well I ah, I lost a pretty big bet.”
“Really, sounds like a pretty wild situation.” Then there was a pause. “I’m sorry, I don’t usually pry so much, I guess I am just fascinated,” she said looking up at me.
“Oh you’ve been very helpful, I really appreciate it.”
“Well, do you need anything else?”
My mind wandered into the gutter and then returned. “I think this will do it.”
“Ok, well I’ll be ready at the counter.” She turned and walked.
I closed the door most of the way and reached under my new skirt and grabbed my cock and jacked it a few times. I was extremely turned on now. I admired myself in the mirror and wished she would come join me. The moment passed and I changed to my boring guy clothes. Five minutes later I was paying at the counter and she was a little flustered.
“Ok, $135.89, too bad the skirt wasn’t on the clearance rack, but the vest usually goes for $150 on its own,” she said with a smile.
As I opened my wallet, she noted my driver’s license.
“Are you here on business dear?” she asked.
“Yes.”
“Too bad about the bet, I hope it doesn’t spoil a good time.” She said with a coy tone.
I looked at her, my confidence renewed. “Oh it’s not going to spoil anything. Actually, it will be a lot of fun.”
“Is this the first time you’ve had to cross-dress?”
There it was. Nowhere to go. I quickly decided to play along and see where it went. “No, actually it isn’t. I’ve done it a few times.”
“Always for bets?”
“Well, actually no.”
“Really? It must be kind of difficult to need to do that during a business trip away from home.”
“Well, it actually is easier in some ways; I probably won’t run into anyone I went to school with or anything like that.”
“Yes, I suppose so.” She paused. “I have a question, how far do you go for this look? I mean do you have to really look the part or are you just supposed to wear the clothes?”
“Oh, I need to look feminine. It’s all part of the deal.”
“Well it sounds like an exciting get-together.” She said leaning forward and resting on her elbows.
“We’ll see. I think it will be.” I handed her cash with a little laugh and obviously leering at her white bra straining against her cleavage.
She reciprocated the laugh and bagged the items. She held up the bag and asked, “Is the party open to anyone, I would love to see the final product.”
“Well, it is actually a private function, but maybe, if you wanted, you could, ah come by and ah, see me before I go…if you want.” I offered, totally throwing the ball in her court.
She looked over at a couple of teen girls who entered the store. “Well, I don’t know. What time will you be ready?”
“The party begins about seven-ish. I’ll probably be ready around five-thirty or so.”
“Oh, I don’t know. I get off at three thirty and have to pick up my k**s at six. I would love to stop by for a few minutes and see how you look. How about I come by about four-ish? Maybe I could maybe give you some assistance.”
“Sounds great…I’m staying at…”
About three I started getting ready. I was so excited. What kind of freak had I met? What kind of freak did she think I was? What would happen? I was so hard. I was ready about three thirty. I watched porn and fought the desire to jack off. I positioned a Tranny magazine, lube, condoms, and a dildo in plain sight.
At 3:40 she called me and asked if she should still come by. I told her I was ready and the party had been moved up. I said she should come over right now because I had a question for her. At 3:50 I heard high heels walk to my door and then she knocked.
I walked in my heels and hot new clothes to the door and opened it and stood back away from the threshold.
Gail came into my room wearing her own short black skirt herself and carrying a bag from the store. She was wearing a darker lip color than earlier and her eyes seemed darker.
She looked me over and said, “Wow, Holy shit you look great!” she exclaimed. “I love your shoes and the vest…” She paused and covered her mouth in surprise and astonishment, “Oh my, you have done this before, quite a few times.”
I turned around so she could see every side of my body.
“Wow...all I can say is wow.” She set her bag on the dresser and leaned against it and starred at me.
I beamed and continued making little poses. I kept watching her eyes feast upon me. She was definitely a freak of some kind, like me.
“This can’t all be for a bet. Why did you put so much work into it?” she searched.
In my slutty voice I came clean and said “This is all for recreation and fantasy.”
“Oh my god, you even sound great too, holy shit!”
I looked at her in her eyes and she held my gaze. She looked past me to see the toy and lube. I watched as she connected all the dots.
I broke her stunned silence with, “So, what’s in the bag?”
“My other skirt and some stuff I bought on break.” She changed the subject. “You look really good. How long have you been doing this?”
“For a long time.”
“Are you gay?” she asked.
I smiled wickedly as I stepped forward and closed on her and said, “I’m extremely Bi-sex-u-al.” I said licking my lips and looking into her. I closed in even further and looked down her blouse. I reached up and held her firm arms and kept coming in to a kiss. She didn’t resist. Our lips met and my tongue probed her, tasting mint and feeling warm wetness. Her lips were smooth and supple. She felt good. I raised her arms to allow her to grab my leather-clad ass. She was timid at first and then gradually increased the force of her grip. She moved her hands around and fondled my leather clad ass.
I lowered my grasp down her back and squeezed her ass. I stepped between her knees with my stocking clad leg and rubbed against her inner thighs. I reached down and touched the tops of her thighs and began pulling her skirt upward. I enjoyed the feeling of her hot skin beneath her pantyhose.
She broke the kiss. “This is crazy, I…Ah, um...ah have something you might like. Let me go into the bathroom for a minute and show you, ok?”
“Ok,” I said.
She looked up at me and rubbed her hand on my bulge. She smiled and said “Oh my, I thought I saw something earlier. I’ll be right back.”
She took her bag into the bathroom and closed the door. A few minutes later she opened the bathroom door wearing a set of matching red stretch-satin basics. She wore a brand new bra, garter, and panties and she had replaced her pantyhose with black fishnet stockings. She looked hot too.
“How do you like it?”
“I Love it,” I said walking to the bathroom doorway to feel her satin cased breasts. Her body was warm and toned.
She beamed with pride and looked at my dark mascara-and-shadow covered eyes.
I said in my wanton voice. “Would you like me to lick you till you cum in my mouth?”
“Oh my god,” she answered with the slightest of nods.
I slid my hands around her nipples and squeezed them through her red satin bra cups. She squealed a bit. I dropped down and knelt. Then I shifted her panties out of the way and opened her labia.
I met her gaze and breathed her in. She smelled like sweetly mixed body spray and cunt. I put my mouth against her sex and darted my tongue into her. She moaned as I softly licked her in little circles. Gail leaned back into the sink and looked down to watch me. I looked up at her with her sex in my mouth. I licked her and watched her focus on the show. She was sopping wet already. She held herself up by resting her hand on the back of the counter. She propped one leg up on the rim of the toilet. Sooner than I was expecting, her eyes rolled back and she began to cum. She made an ecstasy scowl and began throbbing and moaning.
I reached down and freed my cock and stroked myself. I had a condom in my thigh highs just in case. She seemed to enjoy cumming in my mouth as much as I did.
I ate her out and stroked my stiff seven and three quarters inch cock so hard that I almost came. I took my other hand away from her cunt and stroked her slit and teased her a little. She came down from her orgasm and looked down at me. She smiled and grabbed my hand from her cunt and pulled it up to her tit. She eased my other hand up to her other tit. I massaged and caressed her soft and shapely mature tits. I pushed the bra up and away from her nipples and squeezed. Her tits were very nice, not huge, and not too soft. Her nipples betrayed the fact that she had breast-fed at some point. I squeezed the nipples and sent shocks through her.
She picked my hands up from her tits and beckoned me to stand and follow her to the bed. She had me turn and lay down. I eased myself against the pillows and watched her go down on me with precision and skill. She was a very talented cocksucker. I watched her love my hard cock, protruding from the side of my panties. I noticed her reaching down to work her sweet wet pussy.
This is hot, I thought to my self. I met this talented woman who needs cock and is a little freaky at a store where I was buying slutwear, and now she’s her sucking my dick.
She had her fill of cocksucking and then rose up off me. She looked down at my thigh-highs and fished out the condom. Straddling my thighs and looking at me, she opened it and unrolled it down my stiffness. She grasped the base and guided herself down on it. She leaned forward and pushed her partially covered tits into my face as she began to fuck me with a rhythmic grind. I reached up and held her tits with one hand and with the other I reached back to her ass to grasp her garter covered cheek. I could feel her panties rubbing against my shaft and reached further back to pull them hard and shift them away from my cock. She felt the pressure of the panties shifting and then I realized I’d increased of pressure against her clit. She ground into me and then began to cum again.
We switched positions several times and ultimately she was on her back with her thighs raising her hips and ass off the bed. She rubbed herself as I fucked her. She came several times and was moaning loud.
Then, between an orgasm, she pleaded for me to “Put a thumb in my ass and fuck me hard!” So I did. I reached back and cupped her asscheek in my hand and pushed a thumb up into her wet pussy while I fucked her. Then I brought it back to her backdoor and shoved it with great ease. She came instantly and was moving so wildly that I could hold out no longer.
I pushed my cock into her and came hard. I filled the reservoir tip and the whole head of the condom with the semen she’d earned. Her orgasm continued through mine and she eventually lowered her hips downward onto the bed.
I was hoping for another fuck session, but she’d gotten hers and rolled off the bed and immediately began to dress.
I was still dressed, so I watched her as I peeled the heavy full condom off. I decided to make some small talk. “That was fantastic, I am really glad I went to the store today.” I joked with her, but she seemed to be a little uneasy. “Are you ok?”
“Sure, I feel great, I just haven’t cum like that in a long time. That felt great, you are so hot.” With that she smiled at me briefly.
“I hope you are ok. If there’s a problem, I’m sorry.”
She paused her dressing and looked at me. “No baby, there are no problems, I just, well, I just haven’t done this for a long time and I came really hard, that’s all. I’m a little light headed and running late and I need to go. I hope you understand.”
“Oh, ok. I understand. I really enjoyed you. I am glad you enjoyed this with me.”
She merely smiled and went to the bathroom to fix her hair. She came out after touching up her makeup and looking more presentable.
“Gail, I would really like to play with you again. I’ll be here in the afternoons and evenings for the next few days. Please call if you would like to play together. Bring a friend if you want.” I offered.
She looked at me and smiled and said, “I had a wonderful time with you. You are very talented and incredibly sexy. Take care, dear.” Then she proceeded to kiss me and walk to the door. Then she turned abruptly and wrote her cell number on the motel scratch pad. She turned and hugged me briefly. Then she saw herself to the door.
I closed the door and watched her go to her car and drive off. She never told me what the sudden change of attitude was. Was she married? Was she a lesbian who needed cock and felt bad about her mate? Hmmm.
Oh well, who the hell cares, I was feeling too good to be concerned about any of her issues. My cock was semi-rigid and it knew this was only a prelude to the night’s affairs.
Two days later Gail came by for a bootycall at three am. I had just returned from the adult theater where I had taken on well over twenty hot ass-fucks and blow jobs. She and I fucked and I told her about my time at the theater.
She stayed for a sloppy second helping and confessed that she had really been questioning her sexuality after our first time. Apparently, I’d caused a craving.
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