Jenny , Mike: A Day out

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May 16, 2023 // By:analsex // No Comment

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I woke up in the morning with Michelle’s arm around me. We were spooning. She was the big spoon. I held on-to her arm stroking it gently as I recalled how ‘Mike’ and I had gotten it on in the living room the previous night. ‘Mike’ had fucked me on numerous occasions in the past, but my ass was still sore after what we had gotten up-to last night! God it was so hot! I turned my head to look at the clock on the night-stand and saw that it was 9:30 a.m. I slowly lifted Michelle’s arm from around my waist, and carefully got out of bed, trying not to disturb her. I noticed in the mirror that my blonde wig was disheveled, just like Michelle’s hair usually was in the mornings. I grinned at my reflection. I continued to admire myself in the black satin chemise I was wearing. It was one of many items of women’s clothing in my wardrobe. I looked back lovingly at Michelle in her boxer briefs and white tank top. She looked so damn sexy in them. I made my way into the kitchen downstairs and got a pot of coffee going. Michelle was always up early and made the coffee, but last night’s activities took a lot out of the both of us, especially her! As I stood at the kitchen counter waiting for the coffee to brew, I felt her arms wrap around my waist. Michelle leaned into my back, and kissed me on the shoulder. “Good morning babe,” she said playfully. “I didn’t hear you coming…downstairs.” “I thought I’d sneak up and surprise you,” she said, kissing my shoulder again and squeezing me tighter. “I could get used to…this.” I turned around and looked lovingly into Michelle’s eyes. She reached up and stroked my cheeks, before pulling me into her for a soft and tender kiss. I wrapped my arms around her, deepening out kiss. The beeping coffee machine pulled us out of our loved-up trance. “Coffee’s ready, I guess,” I said, breaking the kiss and clearing my throat. Michelle burst out laughing at my sudden bashfulness. We settled opposite each other at the table to enjoy the coffee I had just poured for us. I took small sips of the hot aromatic coffee. “What?” I asked, as I realized Michelle was looking at me intently. “You look so sexy dressed like that,” she said with a smile. “What?” “You heard me.” “With my hair all over the place? I look like a muppet!” “Ha! No way! You look cute, babe,” she said laughing. I frowned as I continued to sip my coffee. Michelle, on the other hand, was still smiling as she sipped hers. After our morning coffee, I went about taking care of the chores Michelle usually performed on Sundays. After I headed back to the kitchen to prepare breakfast, Michelle was still sat at the table reading the morning paper. I rustled up a breakfast of bacon, scrambled eggs and toast and served it up. “So, what do you want to do today?” Michelle asked as we tucked in. “I don’t know. You kind of sprang this whole long weekend thing on me.” “I was just as surprised when Henry told me that I could take today and Monday off.” “What do you want to do today?” I asked, taking a bite. “I was thinking that… we could go out today and grab some lunch…” “But I thought you didn’t want to break character?” I said, puzzled by the apparent about turn. “I was hoping that we could go out as ‘Jenny’ and ‘Mike’…” she said hesitantly. My face fell. I felt a rush of anxiety. Michelle must have known that her suggestion would be met with a considerable amount of unease from my side. “Babe…” she said, reaching across the table to take my hand in hers. “Honey, you know I don’t want to go out as ‘Jenny’.” “But…” “After that outing last year, I don’t think I could ever go out dressed as Jenny again.” “Sweetie, that was almost a year ago and where we went wasn’t really the friendliest of places in the city.” I was already going back to that memory. Michelle had, after much discussion, convinced me that we should go out dressed as ‘Jenny; and ‘Mike’. She took me to a nice restaurant. It was nothing fancy, but very romantic. Unfortunately, many of the diners kept staring at us and giving us dirty looks. I could hardly concentrate on my meal or even talk to Michelle. One older gentleman went as far as to leave the restaurant, mumbling under his breath and giving us a dirty stare as he passed our table. It was unsettling. Needless to say we did not enjoy the evening. I’ve not had the confidence to go out as ‘Jenny’ since. “Michelle, you know why I’m uncomfortable. I don’t want to go someplace where people will stare at you and your cross-dressing husband.” “Babe, we’ve discussed that night. I didn’t know that our evening would be ruined like that. I feel kind of responsible for what happened that night. I just wanted to go out on a date and have a nice romantic time.” “I don’t blame you… honey.” “I know you don’t. I was hoping we could try it again. But this time we could go out to a friendlier part of town. Maybe grab a bite to eat. Maybe even do some window shopping.” “A friendlier part of town?” I asked, somewhat more interested now. “We could go to the Valley. They have great shops and really good restaurants and pubs.” I sat silent as I thought about it. The Valley was an area in the city that was filled with people from the LGBTQ community. There were a lot of same sex couples Escort ankara that lived and frequented the area because of the atmosphere. It was a safe haven for people with alternative lifestyles. “But we’re not a same sex couple,” I protested. “That’s doesn’t matter. That area is very neutral towards all people, no matter who they are. I have even read on some message boards about men who dress up as women who go there and love it. I’m absolutely sure that we won’t have any problems there at all.” I sat in silence as I considered Michelle’s suggestion. The Valley was filled with people from the LGBTQ community. A lot of same sex couples lived in, and frequented the area because of its tolerant atmosphere. It was like a safe haven for people with alternative lifestyles. “But we’re not a same sex couple,” I pointed out. “That doesn’t matter. I’ve researched online and a lot of straight couples visit the area too. I have even read about men who dress up as women who go there and love it. I’m absolutely sure that we won’t experience the same prejudice there.” I pondered everything Michelle had said. I still wasn’t convinced that going out as ‘Jenny’ was such a good idea. “Just once please, babe. For me. And if it turns out to be a bad experience, we’ll leave and I’ll never ask you to go out of the house as ‘Jenny’ ever again.” I sighed. “Okay.” I knew when to throw in the towel. Michelle was giddy with excitement. “Really?” “Yes. But if it gets to be really uncomfortable, then we are out of there! Agreed?” “No problem. Scouts honor,” she said, raising her fingers in the air. “Okay then.” She got up and came around the table to settle on my lap. “I can’t believe we’re going to do this!” “I love you, Michelle. You know I would do anything for you.” “I love you too, babe.” The look she then gave me, made me fall in love with her all over again. As the morning passed, I became more and more excited and less nervous about our trip to the Valley. After breakfast we decided to hop into the shower together. Sharing a shower with your lover is one of the most erotic experiences you can have. Michelle had her back to me in the shower and decided to turn the heat up a notch. I lathered some of our favorite shower gel and rubbed all over her breasts as I pressed her back to my front. At first I massaged them quite gently. Just the way she liked it. She turned her head and kissed me as I paid more urgent attention to the task at hand. I began edging my hands downwards rubbing the gel all over her tummy, and then finally going down below. She sighed as my hand made contact with her pussy. I started to rinse her, moving my hand down to her pussy, teasing her and eliciting soft moans from her. My cock was at attention and poking against her butt as I slowly edged her towards orgasm. Her breathing became shallow and soon came in gasps. All I wanted to do was to slam my cock into her. “Fuck me!” I pushed her against the wall, and aimed my cock at her pussy. She gasped as I pushed my length inside her, filling her to the hilt. I began to move slowly. After a good few minutes of slowly torturing her pussy this way, I began to give it to her hard. She moaned and whimpered. And every now and then I heard her demanding that I should fuck her, that I should give her my dick. My wife had a filthy mouth. Finally she began rubbing her clit. It always drove me wild seeing her play with herself while I had my dick inside her. She screamed as her orgasm hit her. My thrusting grew faster. Then I finally came too, grunting like a man possessed. After we both had finished, I drew my cock out of her pussy. I held her in my arms as the water cascaded over us. Michelle turned around and gave me a passionate kiss. I held her in my arms as we stood under the shower head together. Then her mood changed. She pushed me back against the shower. “That was a freebie. The rest of the weekend, it’s going to be you screaming for me to fuck you,” she said in a sexy whisper. “Now who’s the tease?” After our eventful shower, we helped each other decide what to wear. For ‘Jenny’, Michelle chose a black and white sundress with a black shrug that complimented it perfectly. For ‘Mike’, I chose a pair of khaki pants and a white shirt with roll back sleeves and a pair of boxer briefs, that matched her binder she was going to wear to flatten her chest. Michelle even wore the harness and the dildo we had used the previous night. This time, the boxers and the baggy khaki pants helped to cover the bulge. Finally, Michelle helped me with some light make-up, and then we were ready to go. I was nervous during the whole drive. ‘Mike’ chose to drive, and squeezed my hand. We entered the valley area and parked near the shopping district. If I was nervous in the car, then I was hot mess as we stepped out of the car. ‘Mike’ held my hand tightly, as a sign of trust, and we moved towards the shops. The mian street was bustling with people. Surprisingly no one was staring at us. It was as if no one cared that a woman dressed like a man, was walking hand-in-hand with a man dressed as a woman. We spotted a store that we liked, and ventured inside. Most of the shoppers were Balgat escort women. The sales staff greeted us warmly and welcomed us. A couple of women even looked at us and gave us a smile. The friendly vide put me at ease and I could feel my nervousness slowly disappear. The sales staff directed ‘Mike’ to the section that had more masculine clothing for women who considered themselves ‘butch’. I, on the other hand, was a still a little too shy to look for anything. In the past, Michelle had always shopped for new items of female clothing for me. Or we just made purchases from online stores selling female clothing for crossdresser’s. It was more discreet. Back on the sidewalk having made some purchases for herself, ‘Mike’ stopped in her tracks and pointed towards a store across the street. It was a sex shop! “You want to go in there?” I asked, once again quite jittery with nerves. “Yeah,” she nodded in excitement. “I don’t know.” “Oh come on, don’t be a wuss!” “Babe, its one thing to go shopping for clothes, a sex shop is a different story alltogether…” I let the sentence trail off. “It’ll be fun. We’ll just look around. Who knows, we might even find something we like?” She pulled me towards the store. Except for a woman sitting behind the counter, the store was empty. The woman had bronzed skin, an average-sized chest, with short dark hair. She seemed to be in her early to mid-twenty’s. She smiled as she spotted us. “Hello. How can I help you today?” she asked cheerfully. “I was wondering if you had any toys my husband and I can use?” I was mortified. “Michelle!” The sales woman saw my horrified expression. “It’s okay sir. We get straight couples in here all the time,” she said, encouragingly. “See? Just relax babe.” “Are you looking for anything specific?” the woman asked. “Nothing specific, really. We just saw the store from across the street and decided to come and take a look. Erm, miss…” “Carmen. My name’s Carmen.” “Nice to meet you Carmen.” “Likewise,” she said. “This is James. Jenny actually…” “Michelle!!!” I groaned under my breath, and gave her an icy stare. “… and I’m… Mike…” “Hi Jenny, it’s nice to meet you… and you too… Mike” said Carmen with a Cheshire cat grin, first shaking my hand and then ‘Mike’s’. “So, what is it that you guys are looking for today? Vibrators? Dildos? Harnesses? Sexy lingerie?” “Could you show us some harnesses?” asked ‘Mike’. “Sure, right this way.” She led us to a section towards the back of the shop where a number of harnesses were on the display. As with my female clothing, Michelle was the one who always purchased the harnesses and the dildos. We’ve purchased three harnesses over the past couple of years. Two of them were made of leather and had to be discarded for wear and tear. The third was a cloth harness, much easier to wash and maintain. “Wow, you have quite a selection!” exclaimed ‘Mike’. “Yeah, we have a wide range of pretty much everything. In fact, we are the biggest sex shop in the city. We pride ourselves on being able to meet almost all our clients’ needs,” replied Carmen. “Do you own a harness right moment?” “Yes we do. A Tomboi harness,” replied ‘Mike’. “Briefs or the boxers?” “Briefs.” “Good choice.” “Yeah, I love it.” “You have it on now, don’t you?” asked Carmen, with a grin. ‘Mike’ and I froze and looked at each other. She, in surprise. I, in silent mortification. “How did you guess?” exclaimed ‘Mike’. “Well, I can see a bit of bulge there. Plus a lot of women we get in here are packing,” replied Carmen. “Really?” I asked, finally breaking my silence. “He speaks!” laughed Carmen. ‘Mike’ burst out laughing too. They were giggling like schoolgirls. I was annoyed, and descended into silence again. “I’m sorry. But yeah, we do get a lot of women who pack. It’s quite common these days.” She picked up a harness that was styled like boxer shorts and showed them to us. “This for example. A lot of trans-men prefer these particular pair of boxers. They put in dildos or packers and get on with their daily routines,” explained Carmen. “They look nice,” said ‘Mike’, as she stoked the cloth harness. “They look good, yes. But when you want to play, they don’t have a lot of give at all. I’ve heard from many people that that dampens their experience,” replied Carmen. “Then why do you carry them here?” “Well we have to. Plus this style can also be used as a packer. So they do serve their purpose to some extent. However,” she continued, picking up yet another harness, “this is the harness I stand by. It’s called the Joque, because, as you can see, it’s shaped like a jock strap. It’s a double-strap harness,and therefore very easy to put on. The adjustable Velcro straps at the back make putting them on almost effortless. It’s got a bunch of other straps too which once adjusted, never need to be adjusted again.” “Never again?” ‘Mike’ looked incredulous. “Not at all. Unless you want someone else to wear it, then, of course, you would have to make adjustments.” “Is it comfortable?” “From experience, I can assure you it is the most comfortable harness!” “Any good for pegging?” asked ‘Mike’. I got another horrified look on my face. “Yeah, definitely,” answered Carmen, Batıkent escort bayan glancing in my direction, with a reassuring smile. “Does it come with a dildo?” “Sometimes they come in kits, but this is just the harness. If you are looking for a dildo that will go with it, you would have to consider what type, size and girth for example. Personally, I prefer this one called the Outlaw.” The dildo she held in her hand was a realistic dildo and it was huge! “It’s about nine inches or so. You can also go with the Bandit, which is about eight inches long. Both come in vanilla, caramel & chocolate colors.” “Will these go with the Joque?” “Like I said, I speak from experience.” “Have you… ever… used it… on a guy?” asked Michelle. “As a matter of fact, yes, I have,” replied Carmen, with a smile. ‘Mike’ turned to me, “We’ll take it.” I gulped as I heard her say those words. The dildo we had at home was about seven inches long. The eight-incher seemed ok too. But the nine inch dildo ‘Mike’ wanted to get us to get was massive! “Which color would you prefer?” asked Carmen. “We’ll take both in caramel.” “Great, I’ll ring these up for you then.” I pulled ‘Mike’ closer to me, “You’re buying both of them?” “Yeah. So?” “But that… that other one is… so big… ” I pointed out unnecessarily. “Aww, is my little kitten worried?” teased ‘Mike’. “Don’t worry babe, we’ll try it out. If you can’t take it then we can always use it on me,” she said, with a wicked grin. I was nervous once again, but after all the shopping I had was begging to get a little hungry and tried not to think about the big dildo. We opted for lunch at a bistro across from what appeared to be an old, out of use movie theater. “Look at that, an old-fashioned theater,” said ‘Mike’. “They haven’t listed any movies outside, I wonder if they’re still operating.” “Wait here,” said ‘Mike’, as she headed across the road. My nerves began to act up again as I stood alone outside the restaurant. She ran up to the young man sitting at the ticket counter and exchanged a few words before making her way back to me. “They’re still in business, and they’re showing Casablanca tonight.” “Oh, okay,” I said, as we entered the restaurant. A hostess met us at the door, and guided us to a booth. She handed us a couple of menus and smiled at us as she walked away. “So, I thought that maybe, we could see Casablanca tonight?” said ‘Mike’. “You want to come back here and watch a movie?” “Yeah. I mean, our shopping trip is going so well. No one is staring at us. The vibe here is so great. I thought the movie would be a nice end to our day?” ‘Mike’ looked at me expectantly. “Well, we have had a good day. What the hell, let’s do it.” “Great!” “I haven’t seen it anyway, so… ” “You haven’t seen Casablanca?” She looked at me like I was from another planet. “No. Is it any good?” “It’s only one of the most romantic movies ever!” “Okay,” I replied, laughing. “I first saw it in high school, and I used fantasize that I was Ingrid Bergman,” she said with a sigh and far away look. “Okaaay,” I said, laughing. “Why are you laughing?” “You fantasized that you were a movie actress?” I couldn’t contain my laughter. “Haven’t you ever fantasized that you were a character from a movie or even just someone else?” she asked. I could tell that ‘Mike’ was not going to let this go. I had never been more happy to see a waitress at that moment. “Hi, my name is Melinda, and I’ll be serving you today. Have you decided what you would like?” “Um, no not yet. Could you give us a few more minutes?” said ‘Mike’. “Whenever you guys are ready, wave me over and I’ll be back to take your order.” ‘Mike’ continued to fix me with the enquiring stare she treated me to before the waitress interrupted us. “What?” “I’m still kind of waiting for my answer.” “Well, I mean I used to fantasize, but not really about being a movie star or anything…” I let the sentence trail off. ‘Mike’ leaned in closer, looking into my eyes as if trying to pry my secrets out of me. “But there was someone you fantasized about, or someone you fantasized being?” she prompted. I could feel my cheeks heating up as I blushed. I knew I had been caught. “You didn’t fantasize about screwing her, did you? You fantasized about being her,” ‘Mike’ grinned. “Come on, tell me!” “No…” “Oh, come on. I accept you for who you are James. It’s okay. You can tell me.” “No. Now let it go, please.” I made eye contact with the waitress, and gestured her over to our table. “You have to tell me. Maybe we can even do some kind of role-play and get you off,” she teased, grinning. I knew Michelle well enough to know that she would not let this go. And if I told her she probably would end up making that fantasy come true. But I didn’t want to tell her. “So, you’re ready to order?” the waitress asked. “Yeah. I’d like to start with a drink first. A rum and coke please,” I said hastily, welcoming the interruption. “And for you?” “I’ll have whichever beer you have on tap, please.” “Okay, great. I’ll be back with your drinks soon.” ‘Mike’ scooted next to me in the booth. “Tell me. Come on. You know I’m not going to let this go.” “Just leave it, please.” “James, please. Tell me. I have accepted everything about you. I am not going to judge you. This far into our relationship, you don’t trust me?” “It’s not about trust. It’s just kind of embarrassing.” She looked a little puzzled. I could see that she was trying to figure out why I was so reluctant. “The maid who came my parents house twice a week.

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