Part 2 - I've only ever dated women and have only ever had sex with women, but my secret lingerie fetish led me down an unexpected and exciting path to explore my bi-curious fantasies. Much of this story is inspired by things that I have actually done and/or experienced, but I'll leave it up to you to decide what parts are reality and what parts are fantasy.
I was both anxious and excited now knowing that there were other bi-curious guys out there and that they wanted to have sex with me as much as I wanted to have sex with them. It didn’t feel real and I was a bit paralyzed with indecision about whether or not I should, or even could, take the next step.
As much as I had safely fantasized in my mind about having sex with another guy, the possibility that it could actually happen was overwhelming. My thoughts returned to my wife and if this would, in some way, be cheating on her. As I struggled with this, I thought to myself, “Well, what if she wanted to have sex with another woman?” And by that, I wasn’t thinking about a threesome (which would be a no-brainer), rather, just her and another woman by themselves. I convinced myself that I would honestly be ok with it, because that was an experience I could never give her. Similarly, me having sex with another guy is an experience that she could never give me. And, again, this was just about sex, not romance.
After I mentally cleared that hurdle, I thought to myself, “There’s no harm in just checking who my matches were.”
I then returned to the computer and nervously clicked, “See matches.”
I had two matches with the same “No,” “Give”, “Receive”, or “Both” responses that I had given to the profile questions. The first one, Steve, didn’t list anything under preferences, but the second one, Brian, listed “open to experimenting.” They were both good-looking guys, but Brian’s response stuck with me.
There was a link labeled “Meet” under each of their profiles. I asked myself, “Could I actually go through with this? If I don’t will I ever get another chance?” I was paralyzed to either step away or keep going.
My curiosity, fantasies, and desires eventually won-out over my inhibitions as I clicked the “Meet” link under Brian’s profile. “Did I really just do that,” I asked myself? “Is it too late to back out?” But what was done was done. Now, I would just have to wait and see what would happen next.
The next day, when I logged in, there was a message from Brian. It read, “I was excited when I saw that you want to meet. I think we’re a good match. I picked one of the hotels that the website recommended. When can we meet?”
I rush of excitement came over me. This is really happening!!! All I had to do was respond with the dates. Since I had gone this far, I decided I had to see it through.
I responded to Brian, “How about 3 weekends from now?”
He must have been logged in, too, because he responded immediately with, “That sounds perfect. See you then!”
I made up a story to tell Stacy that I had to go out of town on a business trip. I told her it was a serious situation at one of our remote factories, which is why I had to go over a weekend. That was something that had actually happened a few times before, so it didn’t raise any suspicions by her.
The next 3 weeks seemed to go so slowly. I couldn’t stop thinking about what I was about to do, even though I still wasn’t sure exactly what that was. I thought about not going. I thought maybe Brian wouldn’t show up. I thought maybe one or both of us wouldn’t want to go through with it even if we did both show up. A million other thoughts went through my mind.
But then the Friday of the weekend finally came. I had spent so much time dwelling on this that I had to see it through. So, I packed some things and started on the 1-hour drive to the hotel we were supposed to meet at.
We agreed to meet in the hotel bar, so when I arrived, I headed in that direction. The bar was about half full of customers as I searched around the room for Brian. When I couldn’t immediately find him, I thought, “OK, he decided not to come.” But then, as I was just about to stop looking, I spotted him at a table over in the corner. I rush of nervous excitement immediately came over me.
Brian hadn’t noticed that I entered the bar as I walked over to his table.
As I got closer, he looked up and immediately recognized me from my profile photo. He got up from his chair with a smile on his face and extended his hand to shake mine. I smiled back and we exchanged a firm handshake.
As I sat down, the waitress was already at our table, and we ordered a couple of drinks.
I felt an immediate “connection,” which I think Brian felt too, and we were both surprisingly relaxed but also understandably nervous. We started with some cliché conversation that seamlessly transitioned into a more personal discussion.
I said to Brian, “I still can’t believe I’m actually here, and I still can’t believe what I think we’re about to do.”
Brian responded, “I know exactly what you mean. I’ve never done anything like this before, but I couldn’t deny the fantasies I’ve been having for so long.”
I said, “You took the words right out of my mouth.”
After we were a couple of cocktails into the evening and it really felt almost like we were longtime friends, I eventually asked Brian, “So, I’m sure you know you’re a good-looking guy. I bet you had a lot of matches to your profile, didn’t you?”
Brian responded, “Thanks for the compliment. I’m sure you know you’re a good-looking guy, too.” He continued, “I had 5 matches that came up on my profile.”
I asked, “So, can I ask what it was that made you pick me?”
Brian hesitated before answering. Then, he said, “To be honest, all 5 of the matches were very similar, but there was one thing that really stuck with me about your profile.”
I said, “Really, what was that?”
He continued, “Well, that part about wearing women’s lingerie.”
I said, “Seriously? I almost didn’t put that in there because I thought it might be a turn-off for other guys.”
Brian said, “I had never really thought about it before that, but the more I did, the more it excited me. I mean, the thought of seeing another guy all dressed in sexy lingerie and then having sex with him was, well, I don’t know if I can really even explain it, but it was something that would just add to everything else. In fact, to be honest, my cock is getting hard right now just thinking about it.”
That was the real icebreaker, and it allowed me to just completely relax and let my guard down.
I said to Brian as I smiled, “I’m really relieved to hear you say that. I kind of thought I was the only one.”
Brian then asked, “Did you, by any chance, bring some lingerie with you?”
To which I smiled and replied, “Yeah, I did. We can head up to our rooms if you want to see it.”
Brian eagerly nodded and said, “Let’s go!”
When we got up to the rooms, they were adjoining and separated by a door. I went into one room, and Brian went into the other. As I partially closed the door between them, I said, “Give me a few minutes and I’ll be right back.”
This whole evening had already exceeded my expectations, and I was getting really excited at having Brian see me all dressed in my sexy lingerie. I opened my suitcase and took out my favorite pair of turquoise sheer lace panties with the thong back and matching bra, along with the matching silk stockings that had lace trim at the top. I also picked-out a very short green and black plaid skirt that had a zipper on the side, and a tightly fitting matching halter top that tied in the front.
I made sure to completely shave my body before I left home, and I also took a little bit of Stacy’s perfume with me.
As I quickly stripped off my clothes, my cock was already hard and fully erect with anticipation. First, I slipped on the panties. I loved the sensation of the thong slipping between my ass cheeks as I stretched the front of the panties over my hard cock. I then put on the bra and slipped my 40D breasts into the cups. I sat down on the bed as I pulled each of the stockings up my legs. They were so soft and smooth that I couldn’t help but slowly run my hands up and down them a few times. Next, I pulled the tight little plaid skirt up to my waist and zipped the zipper. The skirt was so short that it just barely covered my ass. Finally, I pulled the stretchy halter top over my breasts and tied it in the front. With a final spray of perfume, my transformation into a sexy little shemale was complete.
As I turned to look in the mirror, I couldn’t believe how sexy I looked and felt. I couldn’t wait to see Brian’s reaction.
I fully embraced the girlish role I was playing as I stepped towards the door and softly said, “Are you ready for me, Brian?”
Brian responded, “I can’t wait, come in here and let me see you.”
I slowly opened the door and stepped through, walking as seductively and femininely as I could. Once I got into the room, Brian was sitting on a chair just a few feet away.
His mouth dropped open and he said, “Oh my God. I can’t believe I’m saying this, but I honestly can’t even tell you how sexy you look right now. This is way beyond anything I expected. Can you turn around for me?”
I slowly turned so my back was to him with my knees together, and then I slightly bent over to put my hands on my knees while keeping my legs straight. I knew that the short skirt I was wearing would rise up and reveal my ass and that he would be able to get a good view of the sexy thong I was wearing.
I turned my head back to look at Brian and said, “Do you like what you see?”
Brian eagerly nodded and said, “I can’t even tell you how much this is turning me on. I really want to see your bra and panties.”
I straightened up and turned to face him. I slowly ran my hands over my breasts and down to the bottom of my skirt.
I said in a quiet sexy voice, “Do you want to see my panties? I really want to show them to you.”
I didn’t even wait for Brian to reply as I started slowly pulling up my skirt to show him my panties. The sheer lacy material didn’t really hide anything as he could clearly see my hard cock straining against the tiny pair of panties.
I reached down with my other hand and started swirling the precum that had soaked through the panties with my finger. I slowly raised my finger to my mouth to taste my precum and quietly moaned, “Mmmmmmm.”
I lowered my hand back down and slipped it inside my panties and started fingering myself as if I had a pussy. Brian sat there intently watching as I put on this erotic show for him.
As I withdrew my hand from my panties and lowered my skirt, I said to Brian, “Do you want to see more?”
Brian eagerly responded and said, “I want to see everything!”
I felt a little like a dancer at a strip club as I reached towards the tie on my halter top. I found the end of the tie and slowly pulled it until the knot released and the stretchy fabric could no longer cover my breasts.
Brian was amazed as he said, “Oh my God, your breasts look so real.”
I slipped the halter-top off my shoulders and then moved to the zipper on my skirt. I slowly unzipped it and then turned my back to Brian as I slid it down my ass. When it was halfway off, I turned back to face him as I pulled down the front. The waistband of my skirt got briefly caught on my bulging cock as I pulled it down over my panties, and I then lowered it past my knees to the floor.
Now I was standing in front of Brian with my knees together and wearing nothing but my lacey bra and panties. I felt so sexy and so vulnerable all at the same time.
As Brian eagerly took in the view in front of him, I said, “I’m standing here practically naked in just my bra and panties, and you’re still fully dressed. You really need to take your clothes off... But leave your briefs on.”
Brian didn’t hesitate as he got up from the chair and quickly removed his shirt and pants. I could see that he had completely shaved his body, which was exactly what I wanted. Then he was standing there in just his tight briefs as they were barely containing his huge hardon. I got excited to see the wet spot where his precum had soaked through because it was a sure sign that he was really getting turned on by what he was seeing.
My excitement reached an even higher level as I started thinking about what was coming next. I said to Brian, “Come over here, closer to me.”
As Brian stopped just inches away from me, I went down to my knees in front of him. There was his throbbing cock just inches from my face but still concealed by his briefs. This was the moment I had fantasized about for so long, but I was still incredibly nervous to make the next move. I overcame my nervousness and reached up to touch his briefs with just a single finger. I traced my finger up his briefs and over his hard shaft to where the precum had soaked through his briefs and swirled my finger around the head of his cock through his briefs. I put my finger to my lips to taste his precum as I looked up into his eyes. I could see that he was absolutely loving every second of this.
I moved my finger back to his briefs and slowly ran it up and down the length of his cock as it twitched with excitement. I could no longer resist the intense desire to see Brian’s cock, as I reached up to the waistband of his briefs and started slowly pulling them down. As I pulled them down over his ass, his fully erect cock suddenly sprang free and was pointing straight up right in front of my face. He was completely shaved under his briefs, and his cock and balls were perfect in every way as I took it all in.
My heart was racing as I reached my hand up to touch his cock. As I wrapped my hand around it, I was so excited that I almost thought I was going to have an orgasm right there. I started to slowly stroke his cock and it felt like everything I had always imagined. Even though I had stroked my own cock more times than I could remember, this felt so different in an amazing way. The thought of getting another guy off was driving me absolutely wild.
Brian could see how much I was enjoying myself and said, “Your hand feels so good on my cock. I really want see what it feels like in your mouth.”
I didn’t need any more encouragement than that as I looked up to Brian with a big grin on my face. This was a moment I had fantasized about so often, and now it was about to come true. The excitement I was feeling was overwhelming as I reached my tongue out to lick his shaft. I worked my way down to his bare balls and gently sucked them one at a time into my mouth. I took my time as I worked my way back up the head of his cock and lightly sucked on it. The sensation in my mouth was driving me wild, and I could feel that Brian was starting to breathe a little deeper with excitement.
As I pulled his cock downward and slid my lips over it, I swirled my tongue around the head and then tried to take as much of his length as I could. Erotic thoughts raced through my mind of me being down on my knees wearing sexy lingerie like a little sissy slut while giving a guy a blowjob. It was everything I had ever fantasized about. I could feel my cock straining against my panties with excitement.
I kept working Brian’s cock in and out of my mouth, and I could feel him starting to thrust in rhythm as he fucked my face. I grabbed his tight ass with both hands and pulled him towards me as I encouraged him to thrust into my mouth even deeper.
I could feel Brian’s ass cheeks starting to tighten and his thrusting became more intense as he cried out, “Oh my God, your mouth feels soooo good. I love fucking your mouth. I’m going to cum. I’m going to cum!”
And then he let go with a powerful orgasm as his cum pumped into my mouth. I had wanted to feel the sensation of a guy coming in my mouth for so long that I was just savoring every second of it. I kept my lips tightly wrapped around his cock as I gently squeezed his balls, trying to get every last drop of his sweet cum.
As he finally started to relax and his cock slipped from my mouth, I waited for him to look down at me to make sure he could see me swallow his cum. Then, I just said, “Mmmmmm,” as I licked my lips.
Almost out of breath, Brian then said, “I’ve had a lot of blowjobs in my life, but never one like that. That was absolutely incredible.”
I replied, “I really liked doing it.”
After a couple of more deep breaths, Brian said, “I really want to return the favor. I can’t wait to feel your cock in my mouth. Let’s go over to the bed.”
I got up off my knees and moved over to the bed and laid on my back.
As he looked at the raging hardon in my panties, he said, “I really want you to get your cock out of those panties.”
I excitedly reached down and pulled my cock and balls through the tight leg opening on the side. Now that my cock was no longer constrained, it quickly swelled-up and became fully erect.
Brian got on the bed next to me and looked me over with anticipation. He placed his hand on my breast and lightly squeezed it as he said, “Holy shit, I can’t believe how real your breasts feel.” I slightly arched my back to encourage him to fully enjoy them, which he did.
He then turned his attention to my hard cock where drops of precum had leaked out. He took his finger and swirled it around my slippery cock head and then raised it to his mouth to taste. He quietly moaned, “Mmmmm. Your precum tastes so good.”
His hand then went back to my cock and he started lightly rubbing it and reaching down to gently squeeze my balls. He was completely transfixed on my cock as he said, “I’ve been wanting to touch another guy’s cock for so long. I can’t believe how good it feels in my hand. And seeing you wearing these lace panties is a real turn-on.”
He started slowly stroking my cock, savoring every up and down movement.
After a couple of minutes, he said, “I have to feel your cock in my mouth. I want to taste it so bad.”
He then moved down and started slowly licking up and down my shaft and balls. He had positioned his body in a way that I could see his cock was getting hard again. I reached out with my hand and started stroking his cock as Brian took my cock into his mouth.
I think a guy probably knows how to suck cock better than a woman because, when you have one, you know what feels good. And even though Brian had never sucked a cock before, he was doing it in a way that I had never experienced. I can’t really even describe it other than to say that it was absolutely mind blowing.
I got lost in the extreme pleasure of what he was doing, and I could tell by his hard cock in my hand that he was really liking it, too. As he worked to take my cock even deeper in his mouth I could feel I was about to explode in an orgasm. Brian could also feel my excitement as he continued to devour my cock.
As the sensations peaked, I arched my back and just screamed, “Oh my God! Holy Shit!!” as waves of a powerful orgasm rushed through my entire body.
My cum pumped into Brian’s eager mouth and that got him so excited that he came again, too. I loved the familiar feel of his warm slippery cum as I continued to slowly stroke his cock with it.
Brian kept his lips wrapped around my cock to collect every drop of cum. When he felt the last pulse of my cock, he let it slide out of his mouth as he looked up at me with a big smile to make sure I could see him swallow all of my load.
After we laid there for few minutes, Brian said, “I don’t even know what to say. That was so far beyond anything I expected, I’m at a complete loss for words.”
I replied, “I know exactly what you mean, even though I don’t know what you mean.”
We both laughed at that.
I got off the bed and went to pick up my skirt and halter top. We both agreed that it would be kind of weird to “spend the day together” tomorrow, so we just decided to do our own thing and meet in the bar at 8:00pm.
I went back to my room thinking about what we might do tomorrow and how it could possibly be better than what we just did. I took a shower and got into bed. I then had one of the best night’s sleep I’ve had in a very long time.
When I woke up, I couldn’t help but immediately start thinking about what Brian and I would be doing that evening. A big part of the excitement was that we didn’t plan anything specific, so I had no expectations. At the same time, my mind raced in a million different directions about all the possibilities.
It was going to be a long 10 hours before I would find out.