Many years ago, I dated a woman named Hannah. She was about 5’4”, Asian, a cute body with size B breasts. Her nipples were usually hard, which was difficult to hide unless she was wearing a heavily padded bra.
When we dated, we often talked about our sexual past. The following is a story that she told me several times. I believe it to be true because while over time, she revealed more of the story, it was always pretty consistent.
Hannah always had an exhibitionist side to her and loved it when guys did a double take when she walked past them.
Hannah was in high school in the 1980’s, and dated a guy named Chris for about three years. Chris helped Hannah explore her exhibitionist fantasies through relatively innocent activities like wearing shorter skirts, having her perform a strip tease for him in private and having sex under the high school football field bleachers. She was always worried about her reputation, and even though she fantasized about showing off her body, she could never go through with it, because she was always afraid of getting caught and discovered.
Hannah and Chris decided to break up their senior year since they were going to college in different cities; she was staying in Chicago and he was going to school in Boston. They kept in touch, talked regularly and saw each other when Chris would come back to Chicago to visit family. When they did get together and they weren’t in other relationships, they would still fool around just for old time sake.
Chris often asked Hannah if she still had fantasies about showing off her body. Hannah would confess that that was still a fantasy. She even told him that after her junior year in college, she spent part of the summer in the South of France, and she would get so wet going topless on the beach and having male beach go-ers checking out her breasts.
Towards the end of their Senior year in college, Hannah got a voicemail from George. It said, “Hi Hannah, this is George. I’m Chris ____’s best friend and best man. You probably know that he’s getting married this summer and he asked me to reach out to you and chat. Please give me a call back at 617-xxx-xxxx.”
Hannah thought, “Damn it, what a weasel, Chris wants to invite me to his wedding, but doesn’t want to call me directly about it? He’s having his best man do it?” She was tempted to call Chris and just harass him about being a coward, but instead she thought she’d play along and call George back.
When she got a hold of George, the conversation went like this….. “Hey George, this is Hannah. You called me about Chris’ wedding?”
George told Hannah, “Oh yes, I know you heard that Chris is getting married in July after graduation. I’m his best man and I’m planning on throwing him a bachelor party in NY the Friday before his wedding.”
“That’s pretty nice of you, but I don’t think I’m going to the wedding. I haven’t received an invitation,” Hannah told George.
“Yeah, that’s not why I’m calling. Forgive me, if I’m crossing a line, but Chris told me that one of your biggest fantasies…,” he paused, “…is to strip in front of a group of guys, but you could never do it, because you are afraid of impacting your reputation.”
Hannah was in shock and replied, “What the hell. Why is he telling you that? Does he tell everyone about my fantasies?”
“No no no, sorry. He only told me, well because… he wanted me to ask you if you were willing to come to NY and strip for his bachelor party.”
Hannah stopped him and said, “This is a joke right? What the hell?”
George paused a minute, “No, it isn’t a joke, and I’m so sorry. This is such a weird uncomfortable conversation for me.”
“Uncomfortable for you? You are asking me about my fantasies and asking me to be a whore,” Hannah said in an irritated tone.
“I’m so sorry. Chris nor I think of you as a whore. Chris thinks you are beautiful and he’s shown me past photos of you and he’s right, you are incredibly beautiful. He just thought that maybe this was a ‘safe’ way to play out a fantasy.”
“What do you mean ‘safe’ way? I don’t get it,” Hannah started to calm down but was still confused.
“First of all, I really don’t mean to offend you. So I’m sorry. But honestly, this was something that Chris thought you might find intriguing.”
Hannah replied, “Ok, I get it. I won’t take offense that you just asked me to be a prostitute at a bachelor party. Seriously, I’ll just take this as horny boys that want a sexy woman, and I’ll accept the compliment of being a sexy woman.”
George said, “Yes, please. Thank you, that’s exactly what it is. We honestly think you are super sexy and Chris really does think you would enjoy this. So when I said it is a ‘safe fantasy,’ here is the thing. Everyone at the bachelor party will be Chris’ college buddies. No one from Chicago nor in your social circle will ever know about this. If it is true that you have exhibitionist fantasies, you can totally act out the fantasy, as far as you want, and no one will ever know that you did this.”
Hannah was stunned and speechless as she heard George continue, “And we would pay for everything. I’d send you a round trip plane ticket along with some funds for you to buy some sexy outfits ahead of time. We are having the bachelor party in a large hotel suite, two bedrooms connected to a living room, and you will spend the night in the hotel suite. We would pick you up at the airport on Friday and drop you off on Saturday…. You’ve been quiet, are you still with me?”
Hannah replied, “Yeah, I guess I’m in shock. I can’t believe he told you about my fantasies. I can’t believe you are asking me to prostitute myself out. And frankly, I am shocked that I can’t hang up on you. I am a little intrigued. How do I know that the guys will like me?”
“Please, he’s shown us photos of you and we all think you are super hot,” George replied.
“Wait who did he show pictures to and what pictures?” Hannah was starting to get really turned on and really nervous.
“On no no, none of your nude photos, just photos of when the two of you were dating in high school. Just like date and event photos. And only myself and the other two groomsmen saw these.”
“How did you know that there were nude photos?” Hannah asked.
George paused trying to figure out how to respond, “Uh, well ok. Chris did show me some of the nude photos you sent him over the last few years. Without trying to sound creepy, I loved them and I have had a few personal fantasies about you myself.”
“Well I appreciate you being honest, and I guess I always knew that there was a risk in sending Chris those nude photos, but I also knew that Chris hasn’t kept in touch with any of our old friends. I do like the fact that you enjoyed them.” Hannah replied.
George said, “Well I’m glad. You are so beautiful, you should be proud of your body. Look, I understand that you haven’t done anything like this before, nor would you ever do anything like this ever again. We know you aren’t a slut. Everyone has fantasies, and not many people have a chance of living out their fantasies in real life. We are only young once and if we ever do anything which is ‘wild’ we should do it when we are young so we can use the excuse, ‘well I was young and dumb.’ So what do you think? I assume that this conversation and the fact that I saw your nude photos is turning you on. What do you think, are you willing to do this for Chris and for yourself?”
Hannah replied, “Can I think about it for a week? I mean yeah it sounds safe, and it sounds like an amazing opportunity, but I am not a slut, but it might be fun being treated like a slut for an evening. Can I think about it?”
“Of course. If you make up your mind quickly, give me a call and we can get things arranged, if not, let’s talk this time next week?”
So they ended the conversation and Hannah realized that she was super turned on and very wet. She knew that she had to do it, but she wanted to enjoy thinking about the possibilities first.
Hannah and George talked a week later. Hannah said, “Ok, let’s do this. I have some questions though. First off, what are you expecting me to do? I mean, do I just show up to the party and take my clothes off?”
George replied, “Honestly, I haven’t thought about it. I know Chris wants the chance to fool around with you one last time. I assume he means that you two would do that in private. But I think at the very least, we want to see you strip. I’ll probably pick you up from the airport, then take you to the hotel, you can get ready and we will all go to dinner as a group. Then we’ll come back and play poker. I assume you would strip during this time, and afterwards, you and Chris could enjoy some time alone in the bedroom.”
Hannah replied, “That all sounds good, but what if after I strip, I’ll put Chris in the middle of the room and you all can see how good I am at giving Chris a blow job?”
“Uh, yeah, that would be amazing. I’d love to see you suck on Chris’ cock and check out your nude body as you do it.”
“Ok, so let’s do that. Are you expecting anything else? I mean, I assume you know this is NOT a gang bang.” Hannah replied
“No no, this won’t be a gang bang. Just strip and do Chris. I promise you, we will respect your boundaries.” George said.
“Is there any preference on outfits? I assume I should dress sexy but classy for dinner. It should be a warm night in NY, so a skimpy dress that shows a lot of skin would be good?”
“Yes, that sounds good. As far as other outfits, I think some sexy lingerie to strip out of, and maybe some other racy sexy dress or shiny leggings so that you can wear something to socialize with the guys if you finish with Chris before everyone leaves the room. Maybe a bikini to strip out of as well, just leaving options open.”
“All that sounds good. So I’ll look out for the flight information and the clothing allowance and you are going to pick me up at the airport.”
“Yes, that’s all correct. We’ll talk a few days before your flight just to check in, but if you need anything in the meantime, just let me know. Thanks Hannah. This is going to be so sexy.”
“Thanks for asking, I have to say that I’ve been thinking a lot about this for the last week and I’ve been super turned on about this.” Hannah replied.
George then said, “Can I ask you one last favor? Can you send me a few sexy photos of yourself? I’ve actually been fantasizing about you stripping at the bachelor party and I wish I had some actual pictures to use during those fantasy times. Obviously Chris won’t share his nude photos of you, could you send me a few?”
Hannah laughed, “Sure, as long as you promise not to share them with anyone.”
“I promise Hannah.” They ended the conversation there. Hannah, as promised, sent a whole set of super sexy nude and semi nude photos to George.