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First date in long time It was his first date in a long time decided to go on a dating site. His partner was no longer around and the moved out and lived their own lives. He decides to go onto a dating site and puts a few pictures of himself up wearing short sleeve shirts and shorts. After being on a week chatting with women he has a conversation with one that leads to a date that is to take place 2 weeks later. He continues to chat with others remembering the different dates he had over his lifetime before losing his partner. The gentleman is nicely groomed, shaved facial hair, and trimmed his pubic hair so it is low almost bald. An untucked collard shirt that is short sleeves and buttons down, shorts that are dressy, and loafers that bring everything together. He leaves himself time to pick up flowers at the local florist then drives to her place to pick Julie up, knocks on Julie's door, and the door opens he says hello Julie says hello b takes the flowers, and welcomes him into her place. The gentleman is interested in knowing what made Julie start chatting with him. Julie tells him" you see I noticed your arms and legs had no hair on them. You told me that they have been that way your entire life. Would you mind if I feel your arm to see if it is as smooth as they look". The guy is like sure ok reaches up towards Julie allowing her to feel how smooth his skin is. Julie asks "do you moisturize at all so smooth like silk stockings? Have you ever felt silk stockings on a pair of legs before? The guy says it has been a while since my wife passed and the only time she would have worn them is when we would have been when we went to affairs. Why are you going to wear some tonight"? Julie says not tonight as it will be kind of cool for me Julie jokingly says " would you try a pair of silk stockings on and tell me what you think of them"? To her surprise he asks would that make you happy for me to try them on and tell you what I think of the silk stockings? Julie takes him by the hand and leads him to her bedroom and tells him to remove his shoes, socks, and shorts. He sits on the edge of the bed and to break the tension in the air says jokingly would you like me to remove my underwear and put on a pair of your panties and begins laughing and laughing until she turns around and in one hand Julie has a pair of silk stockings and in her other hand, she has a pair of panties that match the stockings. Julie leans in slowly, firmly kissing him on the lips whispering yes put the panties on too and I am sure you would agree how weird it looks men's underwear with stockings. The soft passionate kiss has him agreeing with her and just asking if she can turn around it has been a long time since he has gotten naked in front of anyone. Julie quickly turns around allowing him to slide down and step out of his underwear slides the panties on and asks Julie can you help me put the silk stockings on, please. As Julie gets the silk stocking on one foot she feels how hairless and smooth his leg is and while sliding up notices how feminine his calf is and so tone. Julie slides the second silk stocking on and as the top sits on his thigh touches the panties caressing the panties noticing he is getting excited a wet spot shows but she says nothing at that moment. Julie tells him at this moment I hope you don't mind I told a girlfriend to come over to check on me as was very nervous about us meeting at my place on our first date. The gentleman says " I understand totally a matter of fact was surprised. But you said it makes you feel comfortable because you have a lot of people who were concerned about you meeting a total stranger. Julie gets off of her knees and leans into him kissing him till he was flat on his back and the two of their lips are locked together Julie caresses his thighs covered by the stockings, his panties getting tight and multiple wet spots on the panties. The doorbell rings and knocking on the door follows. Julie Yells I will be right there give me a minute, Goes to her and draws quickly going through them finds a pair of satin black pants tells him firmly quickly put them on your socks and shoes. Julie goes to answer the doorbell and says sorry we were in my bathroom he is so nice took a look at the drippy faucet and unclogged my toilet. Julie yells for him to come out and meet her friend Jaqueline. Elaine and he shake hands, she leans in and says in his ear if things do not work out between you two I will be calling. The guy steps back and says pleasure meeting you Elaine I hope we can all get together sometime. Julie says well actually we are going out with her and her husband and a few other couples. The guy say maybe we can stop by my place and I can get a long sleeve shirt but he really wanted out of the women's pants, panties, and stockings. The women say no time for that everyone is outside waiting for us. The three of them leave with the guy wearing the female clothing and his button-down shirt not tucked in. Julie walks behind him lifts the shirt seeing how his ass looks perfect in women's pants, grabs his hand pulls him closer to her, and whispers in his ear your ass looks so Hot in the pants I want to run my tongue all over it. The guy thinks to himself all I have to do for this woman is wearing this stuff to have sex with her on the first date it's so worth it. They all enjoy one another's company throughout the night. They all go their separate ways with Julie leading him back into her place she turns him around pinning him against the door and unbuttoning his shirt for her to see for the first time he has hair on his chest and a little on his stomach. Julie asks as she is kissing him on the lips moving lips onto his neck would you shave the little hair you have. The guy has such a hard-on like he has not had in a very long time and says sure whatever makes you happy. The guy thinks to self if it means I am getting sex on the first date from this woman sees nothing he gets what he needs so badly and she is happy. Julie leads him to the bathroom takes an electric razor and removes the hair from his stomach, she tells him to lift his arms so it tightens the chest, he lifts his arms she shaves some of the chest hair off and says oops as the electric razor slips up to the armpit removing the little hair that is there. Julie says sorry guess to make them match will shave them entirely but this is what she wanted to give him a totally hairless body like a woman. Julie continues and now he does not have a strain of hair from the neck down on the front or back. Julie begins sucking on his nipples and his already hard penis gets harder than he has had in a long time and is so happy and loving how Julie is making him feel. Julie asks him would you wear something for me that would help make your chest stick out more and would be easier to suck on and orally pleasure in the heat of the moment he says, yes and Julie opens the drawer and pulls out a strapless corset closing bottom clip and working up but the top three would not close until about 30 minutes of Julie caressing his body ass thighs crotch and orally pleasuring his chest. The last three clasps close his nipples and his areolas are totally exposed for her to orally pleasure. Julie asked if he can sleep over or if he is busy tomorrow. The guy is not sure as he did not bring a condom thinking he was not looking to have sex on the first date and tells Julie I did not bring any protection but can stay over. Julie says "well there are other things we can do besides you penetrating me which we will do when I go back with you to your place tomorrow. I need you to wear clothes to bed as do not want your body oils to get on the sheets Please". The guy agrees to wear what she has. Julie says to make sure you do not get up in the middle of the night You step into this and it applies pressure so if you ever feel like the need to go to the bathroom this will make the urge nonexistent. The guy takes the item steps into and asks Julie to please pull the zipper up on the side. The guy asks what is this called and Julie tells him it is a tummy tucker and applies pressure on the tummy and between the thighs it is something men wear to bed to make sure they do not need to get up in the middle of the night, the only thing is some men have been known after wearing it for to long of a period find it challenging to get or hold an erection but you seem like a healthy male so have no worries. Julie makes sure he does not try to get the corset or tummy tucker off so slips a bar in the lace attaching a lock to the zipper of the tummy tucker and a bar with a lock at top of the corset. Julie tells him to raise his hands and has a nightgown that if it does not fit can be opened at the seams. He tells Julie ok this is so weird am not comfortable I think I want to leave. Julie says I am sorry but all your male clothing has been put in the laundry let me open the seams to show off your cleavage I mean breasts mean chest, bends down opens the seams by the thighs caresses his stocking-covered legs kisses them leaving lipstick marks. He tells Julie you are making me wet the panties with precum but cannot even feel if am getting an erection. Julie leads him to bed to cuddle and watch a movie. He dozes off quickly in Julie's arms and Julie slips a meditation hypnosis recording having his desire to wear women's clothing whenever Julie wants and he desires women's clothing more than male clothing. The next morning Julie wakes up before him making sure the earbuds are taken out of his ears. Julie leans in and kisses him on the lips waking him up, he smiles at her. He says I had the weirdest dream last night not sure if should share it never had a dream like this before. Julie says please share it means so much at the beginning of our relationship you can confide in me. The guy understands and explains he had seen himself going shopping for women's clothing thigh high boots, makeup, skirts, blouses, and walking around in public modeling for you and us going out as two women. Julie says wow sound so sexy it has me tingling starts kissing him in his cleavage looks up and says I do have some of the items but not all would you like to try some women's clothing on. The guy Smiles at Julie and says Yes Please. Julie walks him to her bathroom and sits him in front of the mirror facing her so his back is to the mirror. Julie tells him I want you to have the full experience so am putting makeup on you. He is concerned and asks is anyone supposed to come over like yesterday, Julie flat outlies and says no, absolutely not no one was asked to check on me. He is made to feel safe it is just between her and him. Julie goes to town applying foundation blush eyeshadow eyeliner and lipstick. He notices behind Julie is all the women's clothing they spoke about and some he never mentioned that were in his dream. He is confused as he knows he was sleeping but how is it she had everything laid out before he told her? Julie tells him to stand up and step into the skirt, he does as asked thinking it would be about the knees but when it was up all the way it was more than the middle of the thigh high. Julie places her hands on his shoulders pushing him to sit again so she can slip on women's shoes with thick 4-inch long heels and watches Julie lock them on his feet, he asks why Julie responds to make sure they do not slip off and you do not hurt yourself what other reason could there be silly. Julie asks him to lean away from the back of the chair so she can put the blouse behind him and tells him to slip his arms into the sleeves that are so short just barely cover the shoulders. Julie tells him to stand and she buttons the blouse closed as much as possible but because his breasts are so big can not close the top three buttons. Julie has him sit down again and slips on a blond wig with highlights that match his eyebrows. Julie has him stand all pretty and made to look like a woman the best Julie can. His mouth drops wide open never thinking his body could look as much of a woman as he sees in the mirror. He is in shock at what makeup can do, the wig looks like real hair and it matches his eyebrows so nicely. They hear the door and it is Julie's friend Elaine Yelling "Good Afternoon SleepyHead. I want to hear all about your date last night well what you two did after you left us". Julie quickly goes to Elaine and makes up the story sorry after we left the group my friend from college called and asked to sleep over so nothing happened. Elaine says " A friend from college would love to meet her". Julie says well we were just getting ready to go out for some therapeutic shopping she is having a difficult time she just broke up with her man. Julie Yells " Abigale come here and meet Elaine before we go out for some therapeutic shopping just the two of us". The guy is ever so slowly walking as if not knowing if he should as if does not know will pass as a woman. Julie meets him halfway and says to him "say nothing just nod and moan sadly as I told Elaine you just broke up with your man and how sad you are so she does not stay and want to talk the only way I could think of u getting out of here without her joining us is therapeutic shopping Sorry really really Sorry not what I had in mind happening today". You said nobody would see me like this but you. Julie says " ye yes I know but she will ask a million questions if we don't leave. I will make it worth your while. I will give you a blow job in a woman's dressing room and bathroom. Julie takes his hand and walks him so they can leave. Julie holds onto Abigale tightly so does not have to walk in a regular stride hiding how she is getting use to the women's heels shoes locked onto her feet. Abigale had a pair of sunglasses she lifts to her face to cover her eyes as if she had red eyes from crying so much but it is actually to cover more of her face. Elaine says " am sorry to hear about your breakup but I know a day out and about trying on lingerie and pretty clothes always makes me feel better till I get the bill at the end of the month" and giggles. Elaine says her goodbyes to Julie and Abigale allowing them to lock up the place and go shopping. Julie drives them to the industrial park where there was a warehouse sale and low volume of people. Julie looks around sees no one getting out of any other vehicle and Abigale says I got to go to the bathroom whispering in Julie'a ear. Julie tells Abigale go behind the dumpster and squat so no one sees you pissing and more importantly a female would squat to piss in such a place not stand. Abigale says " are your serious". Julie says " yes it is either that or the woman's room which am sure others would be using". Abigale says " Fine" When they finally walk into the warehouse Abigale starts walking towards the male section and Julie quickly grabs him saying " You need to stay with me people here will not understand a woman looking at male clothing in her size". Julie gabs and says to Abigale at the same time " I am taking you to the bathroom so you can learn how to sit like a woman and piss and if you do not do it properly will slip a cage over your penis and lock it up till the time we are no longer together". Julie & Abigale get to the women's bathroom your typical dark, dirty, and dingy warehouse bathroom. Abigale is extremely nervous so she takes guidance perfectly thinking doing so he will be rewarded dabs himself to make sure does not leak onto undergarments. Julie kneels between Abigale's legs slips on a cage and locks it in place and softly whispers for Abigale to stand and place his hands flat on the walls. As Abigale does Julie opens her pocketbook and pulls out a butt plug and inserts it into Abigale and tells her to get herself together which will help keep the butt plug in some. Abigale clinches her lips together as the butt plug is pushed in, slowly pulls up panties, and makes sure before they leave the woman's bathroom everything is perfectly straight and he looks proper. A group of 20-something-year-old girls passes them in the hallway and one of them turned her neck so fast could have gotten whiplash and said I would like a toy like her meaning Abigale. Julie and Abigale are looking in the women's section and the girl comes over to Julie I love how you have your girlfriend all pretty was wondering what did you have to work with from the start. Julie takes her phone out and says here are pictures out with friends places we have gone as a traditional couple and pictures showing how I transformed him to be such a well-behaved gurl if you want to come over tonight or tomorrow morning here is my number text me and let me know when. |
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good,had me getting a wet spot in my panties,would love to read more of this story
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