Part 3 - 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 started the day by showering and making sure my entire body was smoothly shaved. I got dressed and killed some time by running a few errands, watching TV, and doing some things on my laptop. The clock felt like it was moving so slowly, but when it finally got to 8:00pm, I excitedly left my room and headed down to the bar.
I was thinking this might be a little awkward considering what Brian and I had done the night before, and especially the way I was dressed and acted. But I decided what was done was done and I’ll just go with the flow.
I found Brian at the same table as the prior night and, as I took a seat, I wasn’t quite sure how to start things, so I just said, “That was some night last night, wasn’t it?”
Brian replied, “Yeah, it sure was. That’s all I could think about all day.”
That seemed to ease the tension and we both relaxed.
After the waitress brought our drinks, Brian continued, “You know, to be honest, I wasn’t sure what to expect yesterday with the whole lingerie thing, but it really blew my mind. I mean, you really made it work.”
My face must have turned a dark shade of red when he said that, and I just replied, “I’m glad you liked it. I don’t know, it’s just something that really turns me on.”
Brian then asked, “So, do you just have that one outfit?”
I replied, “Well actually, I have a lot more. To be honest, I don’t really even know how many.”
Brian asked, “Did you happen to bring any of the other outfits with you?”
I said, “Well, I actually brought all of them because I didn’t really know what to expect. I wasn’t sure if I would even get to wear any of them.”
Brian then hesitated for a moment before he said, “I haven’t been able to stop thinking about it all day, but do you think I could try one of them on?”
I could feel my cock twitch a little with excitement as I replied, “Absolutely. I’ll take them all out so you can see what I have, and then you can pick whatever you want.”
At that point, it was pretty clear that we were both starting to get really excited by our conversation, so as we finished our drinks I said, “Let’s go back to our rooms and see if you can find something you like.”
When we got back to our rooms, I told Brian to wait in his room and give me a few minutes so I could unpack the lingerie I had brought with me. Once in my room, I unzipped the suitcase and started laying all of the lingerie out on the bed. I even surprised myself how large my collection had grown, and I was getting even more excited as I picked up each pair of skimpy panties and lacey bras and stockings and placed it all on the bed.
Once I had everything ready, I opened the door that connected our rooms and called Brian in. As he entered the room, his eyes grew wide with excitement while he looked over the collection.
He said, “Wow, you weren’t kidding when you said you had more than one outfit.”
I just kind of laughed and replied, “Yeah, I guess I lost track of how much I've bought. In fact, I can see quite a few things in here that I haven’t even worn yet myself.”
Brian walked around the bed and was picking different bras and panties to get a better look at them and then laying them back on the bed.
As he perused the collection, I said, “Take your time and look at everything. I’ll go wait in your room while you pick out something you like. But I want it to be a surprise, so once you’ve made a choice, put it in this bag and bring it back into your room. I even have a second pair of breasts right over there that you can use.”
Brian had a big smile on his face as I left the room. I took a seat in his room and could hear him moving around but couldn’t see anything he was doing.
After about 15 minutes, he came through the door with his bag and said, “I found some things I really like.”
I replied, “I thought you might. I can’t wait to see what you picked.”
Brian then said, “There’s another thing I want to ask you.”
I said, “Sure, what is it?”
He continued, “I want you to get dressed up again, too.”
I responded, “Really? I wanted to, but wasn’t sure what you were thinking.”
Then he said, “I really liked what you wore yesterday, but I want you to show me something different.”
I said with a smile, “I think I can do that.”
With that, I returned to my room and was getting even more excited thinking about the unknown things that we were leading up to. I looked at all the outfits on the bed and knew exactly what I wanted to wear.
The bra and panties I ***********ed were all sheer lace and an erotic shade of red. The bra was lower cut than any of the others that I had, so my nipples were just barely covered even though you could still clearly see them through the sheer fabric. My 40D breasts were pushing out of the top as the tiny bra desperately tried to contain them. The panties were also very small and tight, with sexy little rhinestone clasps on each side of the extremely thin waistband that seemed as if could just snap at any moment. I needed every single thread of fabric to keep my bulging cock inside these tiny panties. The thong on the back of the panties had a heart-shaped cutout at the top that descended down into a single lacy strip between my ass cheeks. The stockings were sheer and silky that felt so smooth to the touch, with sexy lace trim at the top. The garter belt also had little heart-shaped cutouts on the front and back where the straps were attached to the waist. This was definitely a very feminine outfit, but also a little slutty at the same time.
I ***********ed a very short red plaid skirt with lace trim on the bottom and an elastic waistband and slipped it on. Like the skirt I wore yesterday, it just barely covered my ass. I then took the matching halter top, slipped my arms though it, and tied it in the front so the stretchy fabric was pulled tightly over my breasts.
I turned to look at myself in the mirror and thought, “Wow, if he liked what wore yesterday, this will really blow his mind.”
I was waiting for the cue from Brian when I heard him call out from the other room, “OK, I think I’m ready.”
I paused for a moment before I walked through the door. I know wearing sexy lingerie really turns me on, but I never really thought about how would feel seeing another guy wearing it. It didn’t really make sense, but at the same time, I got a little anxious and apprehensive about how this was going to play out.
I told myself I was overthinking it, so I slowly walked through the door with excited anticipation to see what Brian was wearing. As I turned into the room, I found him sitting on the edge of the bed holding his knees and ankles together. We were simultaneously trying to take it all in as we looked each other over.
Brian spoke first and said, “Wow, you look really hot in that outfit!”
I asked Brian, “Can you stand up so I can get a better look at you?”
Brian slowly stood, and it was then that I could fully look him over.
I immediately recognized the outfit he chose and it was one of my favorites. He was wearing a very sheer hip-length white lace robe with a satin ribbon tied around the waist. Even though the robe wasn’t completely see-through, I recognized the outline of a small pair of lace thong panties in an erotic shade of blue. I knew the back of the panties had a sexy little lace triangle at the top of the thong, and the matching bra had some lace detail on the straps and was also very sheer. The matching silky thigh-high stockings had lace trim around the top.
With breasts filling-out his bra and the robe barely covering his panties, I was getting really excited. It was at that moment I realized that Brian wasn’t really a man to me anymore. He had become this sexy woman; a sexy woman with a big hard cock in her panties, just like me. Any hesitation or apprehension I may have had immediately vanished. I mean, a hard cock never lies, and mine couldn’t have been any harder.
He asked, “So, what do you think?”
I said, “I don’t know what I’m thinking right now other than you are really turning me on in that lingerie.”
All of my apprehensions had completely disappeared.
Brian sat back down on the bed and said, “Why don’t you come over here?”
I did as he asked as he spread his knees to allow me to get closer to him. He placed his hands on the back of my legs and slowly slid them up under my skirt to grab my smooth bare ass. His hands then slid around my hips as he slowly lifted my skirt to get a better look at my little red lace panties. My swollen cock was straining against the lacey material as he started gently rubbing and squeezing it. He then slipped his hand into the leg opening and pulled my cock and balls out of the side. My cock quickly swelled to its full length once it was no longer constrained by my panties.
Brian then turned his attention to my breasts as he placed his hands on them and started squeezing. He found the tie on the front of my halter and slowly pulled the loose end until the knot released. The stretchy fabric instantly popped off of my breasts to expose them, while Brian continued to squeeze them.
I removed the halter from my shoulders and let it drop to the floor as Brian moved his hands to the waistband of my skirt. He started slowly pulling it down as he stretched it over my rock-hard cock. I stepped out of the skirt and was now standing in front of him in just my bra, panties, garter belt, and stockings.
As he intently looked up and down my body, I said to him, “I’d really like to see what’s under your robe.”
Brian looked up at me with a smile and said, “I thought you’d never ask.”
With that, he slowly untied the satin ribbon around his waist and pulled the robe open. As the lacey robe fell off his shoulders and back, I felt my cock twitch with excitement when I saw how hot he looked in the sheer blue lacey bra and panties.
He then turned his attention back to my hard cock, just inches in front of his face. He took it in his hands and then started slowly running his tongue from my balls up to the head of my cock that was dripping with precum. He savored the taste of my precum as he thoroughly licked and sucked the head of my cock.
He then started sucking my cock, again, like I think only a guy could. My head was spinning in ecstasy, and I didn’t know how much longer I was going to last, when he suddenly stopped.
I was breathing heavily and wondering why he stopped, as he said to me, “I’ve been thinking about this all day, and there’s something I really want to do.”
At that point, I was so wound up that nothing seemed out of the question. I just replied, “Anything.”
Brian then said, “I really want to fuck you in the ass.”
A wave of excitement rushed over me as I eagerly said, “I’d love to feel your cock in my ass.”
With a big smile on my face, I got on the bed on my hands and knees with my back to him. I felt so sexy and slutty in my bra and panties knowing I was about to get fucked in the ass by a real cock for the first time. Brian moved in behind me and put one finger under the top of my thong and pulled it to the side. He took the bottle of lube that was on the bed and let it drip down between my ass-cheeks.
He pulled his cock and balls out of the side of his panties and stroked his hard cock with some lube to get it ready for me.
He then slid his slippery cock between my ass cheeks and started sliding it up and down, from top to bottom. The sensation and anticipation I was feeling was overwhelming. I let him feel me spread my legs a little farther to invite him to put his cock in me.
He took the cue and started pushing the head of his cock into my eager hole. As I felt the head of his cock push all the way in, I already knew that this was so much better than the dildo I was used to. I moaned a little to encourage him to keep going. I felt the length of his shaft slowly penetrating me inch by inch when he finally touched my G-spot.
I moaned ecstatically, “Oh, yeah. Oh, yeah. Keep going. Your cock feels soooo good in my ass.”
I felt like the length of his shaft would never end until I finally felt his hips come to rest on my ass. His cock was now all the way inside me and it felt incredible.
Brian could see how much I was loving it and slowly started fucking me. The sensation of his cock sliding in and out of my ass and stimulating my G-spot with each thrust was blowing my mind.
I could hear Brian breathing harder and harder as his thrusts became stronger. He used his hands to pull my hips against him as he fucked my ass more intensely. I could feel my hard cock bouncing up and down and my breasts slightly swaying back and forth in rhythm with his thrusts. I wanted to feel his hot cum shoot inside me so bad.
Brian then started screaming, “Oh my God. Oh my God. Oh my God. I’m cumming. I’m cumming.”
And with that, he released his load into me. I could feel his cock pulsing inside me over and over. The sensation was overwhelming and was everything I had ever fantasized about. I felt like I was right on the edge of a perpetual orgasm, but hadn’t actually cum yet myself.
As I could feel Brian slide his cock from my ass, he said, “I never thought there could be anything better than fucking a pussy, but that was unbelievable.”
After we both caught our breath a little bit, Brian said, “There’s still one more thing I really want to try.”
I eagerly asked, “What’s that?”
To which Brian replied, “I really want to see what it feels like to get fucked in the ass. I could see how much you were loving it, and I want to try it, too.”
I said, “You must have read my mind, because I really want to see what it feels like to fuck you in the ass.”
Brian took one look at me in my panties and my still rock-hard cock and let out a little chuckle as he said, “I can see that!”
Brian moved to get on his hands and knees with his back to me. The sight of him in his bra and panties with his cum covered cock hanging out the side was such a turn on.
I pulled his thong to the side as I applied lube between his ass cheeks. I repeated the same things that he did to me that felt so good by rubbing my hard cock up and down his ass. I could feel his ass cheeks relax a little and I took that as my sign to go further. I pressed the head of my cock against his eager hole and he gave a little moan of pleasure. I pushed a little more as the head of my cock slipped completely inside him. He begged me to keep going, and I was only too happy to satisfy his request. My cock was almost halfway in when I hit his G-spot and he made an audible gasp of pleasure that I recognized from when he was fucking me. As I continued to insert more of my cock, the tightness of his hole was so different than fucking a pussy and it felt so good. Finally, my hips came to a stop against his ass and I was all the way inside him.
I waited for a moment so he could enjoy the fullness of my cock.
He was moaning in pleasure as he said, “Oh my god, that feels so good. Please fuck me.”
I reached down for his cock and was excited to find that he was hard as rock again. I started stroking his cock as I proceeded to fuck him. The sensation of his tight ass squeezing my cock was unbelievable. It felt so good that I knew I wasn’t going to last much longer.
Brian must have sensed it, too, as he moaned, “God your cock feels soooo good in my ass. I want to feel you shoot your cum inside me so bad.”
If possible, that got me even more excited as I stroked and fucked him even harder. He was matching my rhythm perfectly when I could feel every muscle in my body tighten and a powerful orgasm rushed through me. I don’t even know what I said as the intensity of it almost made me dizzy. As I was pumping my hot cum into Brian’s eager ass, I could feel his cock start to pulse as he came again in another powerful orgasm.
As I slid my cock from his ass, I just rolled over on my back and collapsed. Brian did the same in complete exhaustion and satisfaction.
We both just laid there for a while in our bras and panties while our thoughts were filled with everything and nothing all at the same time. It was the complete and total satisfaction of actually living out a forbidden fantasy.
It was still kind of early, so we decided to get cleaned up and head back down to the bar for a drink or two. We joked and we laughed and just had a generally good time.
Before we decided to call it a night and head back to our rooms, Brian asked, “Do you think I could keep the bra and panties that I wore tonight? I’d really like to wear them again.”
I smiled and replied, “You know, it looked so good on you that I really think you should keep them.”
Brian added, “I’m definitely going to be starting a collection of my own.”
Before we went our separate ways, we agreed that it would really be great to do this again someday. We didn’t pick a specific time, we just agreed that if one of us was ever in the mood, that we should contact the other.
When I got home, Stacy asked me how the weekend went and I replied in sort of a work-tone, “It was great. I accomplished everything that I wanted to and even learned a few new things that I didn’t know before.”
She replied, “That’s great, it sounds like it was a really productive trip.”
I said, “Way more than I ever expected. It’s really a good thing I went.”
Life went on pretty much as normal from there, but our sex life progressively took a dramatic turn for the better. As exciting and different as it was to have sex with another guy, there was still nothing like the sensation of fucking Stacy’s warm, wet pussy. Over time, I subtly started encouraging her to be more open and adventurous with our sex life. I even eventually convinced her that we should try anal sex. She said it had always made her nervous, but she’d be willing to give it a try.
After the first time, she enjoyed it so much that it became something she initiated on a regular basis. It even led to her confessing to me that she had always fantasized about wearing a strap-on dildo and fucking me in the ass, but she never thought I’d go for it.
I told her, “Well, it seems like you enjoy it so much when I do it to you that maybe I should give it a try,” as I tried to naively act like I had no experience with it.
When she surprised me one night and came into the bedroom wearing nothing but a strap-on, I quickly stripped off my clothes and said to her, “Well, I’m your little sissy bitch now, so tell me what you want me to do.”
That led to some of the most intense and satisfying role-reversal sex we’ve ever had. As much as I had enjoyed the anal sex that I had secretly had before with Brian, there was something very erotic about the thought of Stacy fucking me in the ass that was a whole different kind of ecstasy. That also became something that both her and I continued to initiate on a regular basis.
Brian and I continued to meet-up every few months and it was always a great time. There were moments that I considered telling Stacy about my secret sex life, but I wasn’t sure if there would ever be a “right time” for that. For all I knew, she might have some kind of a secret sex life, too, and maybe it even included a relationship with another woman. The thought of that actually really turned me on, but I figured if it was happening and she wanted me to know about it, she’d tell me.
Everything was perfect the way it was, but I never imagined what was yet to come.
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