A crossdresser deepens his relationship with the lingerie store owner.
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“Lingerie Shopping Part 2”
A 14 min recording.
It’s about 4:00 PM in the afternoon the day after I came into your lingerie shop. You have just called me on my cell phone:
Me: Hi, this is Jim
You: Hi Jim, it’s Jandi! I hope you don’t mind my calling you, I have your number on file here at the store.
Me: Hi Jandi! How wonderful to hear your voice! I don’t mind your calling at all.
You: Thanks Jim, I have been thinking about you all day and was wondering if you would be interested in having a glass of wine together tonight after work?
Me: Absolutely! I appreciate your asking, I should be done by 5:30, which is the same time you close. What time would you like to meet?
You: Let’s meet at 6:00 PM if that will work for you?
Me: You bet, see you soon!
I’ve just walked into the wine bar and see you sitting in a booth in the back of the bar. It’s a really beautifully decorated bar, very soft and very pretty inside. I walk back towards you smiling. You get up and give me a hug and a soft kiss on the lips.
Me: What a wonderful greeting, thank you Jandi! I love the bar, it’s beautiful!
You: I thought you’d like it and I’m really happy to see you, although I think this is the first time I’ve seen you without any makeup on at all (you say smiling). I hope you don’t think I’m being too pushy asking to see you today, but I really couldn’t wait a whole week. I wanted to tell you something and I’m hoping it’s something you’ll want to hear.
Me: I’m really glad you called, I didn’t want to wait a whole week to see you again either but I was afraid you might take it wrong if I called, like I might be trying to rush something.
You: I’m so happy to hear that Jim, I want you to know that I’ve really been attracted to you for a very long time now but I wasn’t sure if you would want a relationship with a woman. I have always found you to be very kind, funny, smart, and attractive and have wondered if we might develop a relationship outside the store.
Me: Oh Jandi, what a sweet thing for you to say and I’ve been attracted to you for a long time as well. But I didn’t think a woman as beautiful, smart, funny, and sweet as yourself would ever be interested in a guy who is a crossdresser so I never tried to push having a personal relationship. Too be honest I can’t believe I’d be lucky enough to have you interested in me.
You: Well Jim, I’m really attracted to both sides of you, I love the female side I get to see most of the time at the store, but I’ve also seen little glances of the male side when we are just talking about things together. It seems to me that it take a great deal of courage to be willing to let a woman know that you are a crossdresser and share that with her. If it isn’t asking too much or if I’m not being too personal, would you be willing to tell me more about why you crossdress?
Me: It’s not asking too much at all and I really appreciate your interest. Essentially I have always been really strongly attracted to women, but when I was in high school, I was pretty heavy and none of the girls were interested in me at all. So I started to develop this fantasy that I was one of them, I would imagine myself being in the girls locker room changing into workout clothing and seeing all the other girls showering and dressing. I’d be dressing in panties, bra’s, leggings, etc. just like they were. Then as I got older I kept expanding my interest and started shopping for makeup and female clothing. As things changed and society became a little more excepting, I would get a makeover at MAC or call a waxing salon and ask if they would be willing to give me a Brazilian wax, etc. So while I’m not comfortable going out fully dressed as a woman with a wig, dress, etc. I’m very comfortable wearing women’s jeans and a blouse that isn’t too feminine. Also the mostly nude makeup you’ve seen me wear so often. Because I am so strongly attracted to women, my fantasy is always that I’m a very feminine and beautiful girl who is in a lesbian relationship with another beautiful, soft, feminine woman. But to be clear, being a crossdresser and having this fantasy is what I enjoy a part of the time, I am not interested in a sex change, and I’m also not interested in being a woman with a guy. I enjoy being a guy as well in a romantic relationship with a woman.
You: Jim, that’s really so wonderful, and for me at least, it’s a perfect mix of what I would like to find in a partner for myself. I’m mostly attracted to men, but am also attracted to beautiful women, so finding someone like yourself to share both the male/female relationship with as well as a female/female relationship sounds like a dream come true! Again, I hope I’m not being too forward but I’d really be interested in our dating and having a romantic relationship. We already know that we have a sexual attraction to each other (laughing) so that’s a plus for both of us right away!
Me: Jandi, I’ll be honest, I couldn’t imagine anything better than having a personal and romantic relationship with you, you’ve everything I could imagine ever wanting in a woman and certainly far above a woman I ever thought I’d be lucky enough to be with. I’d really love to get to know you better and to see where we might go together.
You: (you scoot over next to me and lean in to kiss me long and deeply on the lips) Jim, I’m so happy that we’re going to be together, I’m sure I’m going to love spending time with both Jim and Kim (smiling) and it’s so sweet that you think of me the way you do. (you snuggle in next to me and lay your head on my shoulders) Can we just enjoy the music, the wine, and the pretty decor together here for a while, do you have to leave soon?
Me: (putting my arm around you and drawing you in closer to me) Yes sweetheart, we can stay as long as you want to. I want to spend as much time with you as you are comfortable with, I’d rather be with you than anyone else so it’s really up to you.
You: I am so happy to hear that Jim, tomorrow is Friday, why don’t you plan on coming over to my house and I’ll fix us dinner. Please plan on spending the entire weekend at my place, I’ll have my assistant Debbie handle the store and we’ll spend the whole weekend together!
Me: That sounds perfect to me Jandi (I lean over and kiss you) I am looking forward to the weekend, maybe on Saturday we can head out to the beach if you’d like?
You: We’ll see, I want to talk more about your dressing and if you are interested, maybe getting you a wig so you can go out fully dressed as well. Also I’m really interested in learning more about your crossdressing and how far you want to go in role playing as a woman.
Me: Sure, that sounds fine, I’ll tell you that I’ve always been interested in learning more about being a girl, there is so much I don’t know. I’d really love to have a woman like yourself teach me about being female and all the things I don’t know since I wasn’t raised as a girl.
You: Well then, you now have a big sister (you say smiling) and I’ll be happy to teach you everything you need to know about being a girl. But not all of being a girl is fun! For instance there is your monthly period which isn’t much fun at all!
Me: I understand, and while I can’t really experience those parts of being a girl, just like I can’t know what it’s like to really have a pussy, feel it get wet, know what it feels like to have fingers or a toy inside me or have a female orgasm, at least I can do whatever is possible to simulate the different good and bad experiences. That first Brazilian wasn’t much fun that’s for sure (laughs)
You: You’re right about that, waxing can be a little painful. It’s going to be a lot of fun teaching you about being a girl that’s for sure! (you lean over and whisper in my ear) And we’re going to have a lot of fun playing our games as well, if you feel between my legs right now you’ll see how much it turns me on to think of you as a girl! I’m so wet again.
Me: mmm, you are so wonderful sweetheart, I love how wet you get, I would love to know what that really feels like!
You: That gives me an idea, I’ll be right back (you get up and head back to the restroom, when you come back to the booth, you press something into my hands) here, go put these on, my panties were soaked and you’ll be able to at least feel what it’s like to have that wetness between your legs.
Me: Oh my god, I can’t believe this, I’ll be right back (I get up and go into the restroom and come back smiling broadly) Jandi, that is such a special treat, it feels so good to have that wetness between my legs and it’s all I can do not to cum in your panties right now.
You: Oh Jim, that’s so exciting to hear, I’m not far from coming either! ( you lean over and kiss me, then reach in between my legs and whisper in my ear) I want you to cum for me while you are wearing my panties (you start rubbing me under the table). I want you to cum right in my panties and then you’re going to give them back to me to wear with your cum in the crotch.
Me: Jandi, if you keep doing that I’m going to cum sweetheart, oh god, here it comes, I’m cuming right now, oh god that is so good, oh i’m cuming so hard!
You: I can feel you squirting, that’s so awesome Jim, it feels so good to feel you cuming in my panties! I can feel how wet they are through your jeans, I’m so wet and close to cuming myself, quick go take off my panties and bring them back to me.
Me: (i get up and hurry back to the bathroom to take off your panties and come back to the booth) Here, but they are pretty messy sweetheart, are you sure you want to wear them?
You: (breathing hard) yes, I’m so close, I can’t wait to put those panties on and feel your cum between my legs, give them to me so I can go put them on (I hand them to you and you hurry to the restroom, then coming back to the booth your lips are parted and your skin is flushed, you snuggle back in pushing close to me and opening your legs. breathing hard you take my hand and put it on your pussy) I’m so close Jim, i’m going to cum very quickly, put your hand on my pussy and rub your cum into my pussy. Oh god yes, I am going to cum so hard, I’m just about there, oh that feels so good sweetheart, oh oh oh I’m cuming , oh yessss, i’m cuming Jim, oh god I think I’m squirting as I cum, ohhhhhh
Me; Jandi that’s so wonderful, I can feel you squirting, oh that feels so good sweetheart, it’s so exciting to have you cum so hard!
You: (your breathing is slowing down) oh my god, I think that’s the strongest orgasm I’ve ever had, oh Jim, it happened so fast, I’ve never cum that fast. I know this is all happening very fast and I don’t want to scare you but I think I’m already falling in love with you! Can you come to my house and spend the night?
Me: Jandi, you are wonderful and really are the girl of my dreams!
You: Let’s go right now, I want to hold you in my arms all night long and can’t wait to wake up with you tomorrow morning.
Me: I love that Jandi, let’s go
We get up and leave the bar together arm in arm.
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The above story was written by a client of mine for a custom recording they wanted made. I did not write it, nor do I claim to. I asked for permission to post it and was told I could for others to enjoy it. No one else has permission to copy it or post it.