Caught in Ex-GF's Underwear Pt. 02

I AM BACK! Super excited to have found this site where I am able to write and express my crazy thoughts/stories for you guys.

It had been a few days since I have seen or heard from Greg. It was about a week or so into summer classes which were pretty easy. It made me happy I stayed for the summer. Over the last few days, I could not stop thinking about what happened between Greg and I. Not only was I caught wearing my girlfriend's underwear...but it was by my gay next door neighbor who is a friend and I think I enjoyed it. Fuck, am I really admitting that I enjoyed it? I had always been freaky and kinky but I never thought about anything like this before.

The way he looked at me and laughed, the comments he made, the feeling on his hand on my ass, giving me a wedgie...it all kept playing over and over in my head. Why couldn't I stop thinking about it? I had never felt so embarrassed and humiliated in my life but for some reason I couldn't shake it.

I was watching a movie around 9PM at my apartment and my phone vibrates. I honestly thought nothing of it at the time and I grab my phone and see its from Greg. I pause the movie and freeze up as my heart starts pounding.

"Heyy Matt! I just got home from my friends. What are you up to?"

Do I respond? What should I say? Why am I overthinking this? I text back.

"Hi I'm watching a movie right now just hanging out."

He responds. "Cool! Do you want to hang out for a little bit?

I start to get nervous. What do I say? I am pretty content watching this movie but my mind began to wonder.

He texts again. "Oh and you should definitely wear that thong again ;)"

Fuck! Did he really just text me that? What have I gotten myself into? I struggle to come up with a response but I finally put something together.

"Good one haha I am down to do something tomorrow but I will probably just finish up this movie and pass out."

He texts back. "Its funny that you thought I was asking. Remember those options I gave you? It applies tonight too. You come over and wear it or I fill people in our your little secret."

My mind and heart explode. Was I really getting forced to wear panties by my gay neighbor? The better question was: why did it start to excite me a little bit? I did not want to put on my girlfriends thong and walk over to my neighbors to hang out but part of me felt like he really had some control over me. I decided to text back and play it cool.

"Hahaha okay I will come over. Give me a few."

I talked myself into thinking he was just joking around having some fun. Maybe he just wants to know I am wearing them to get a laugh. Maybe he just wanted to see if I would do it. I walked into my room and reach under my all socks and pulled out the thong. I put it on and put my sweatpants and sweatshirt back on. Fuck it, he already saw me in it...I can wear it over there as a joke.

As I walked out of my room, I feel the material of the thong cupping my balls and in my ass crack and started to think about when he caught me. Why does wearing this make me feel different and dare I say, naughty? I kept playing it off because I am just a horny individual.

I left my apartment and knocked on his door and he opened right away with a big smile.

"Come on in dude!" He gave me a hug and we sat down on his couch. We had The Office playing on his TV so we started watching that and talking about our day. I started telling him about this project I had for my class and Greg starts to giggle trying to cover his mouth and cuts me off...

"So did you wear them? haha"

I instantly lose my train of thought and start to panic.

"U-h-h umm..."

The smile grows on his face.

"I know you did! Your ass looked too good in them not to wear them again...it would be a shame. Let's have a peak...show me."

I sat there with my mind racing still not sure how to respond to any of this trying to understand exactly what I was feeling.

"Come on Greg we don't have to do this again." I attempt to play it off.

Greg steps closer to me. "I just want to see if you actually wore it over here Matt."

I look down at the ground. I made the choice to wear them and come over his apartment already...I may as well prove it to him. I reach in the side of my sweatpants and grab the side of the thong and pull the light blue material up so he can see.

Greg starts cracking up. "OMG you actually wore them for me! I honestly wasn't sure if you would but I am so happy you did! I think you are starting to like wearing them! You should because you can pull it off with that ass."

This was the first time since Greg originally caught me wearing them that I was hearing his laughter and comments in person. It was sending chills down my spine and was scrambling my brain. I had been imagining him doing this for a couple days now and the fact that it was happening again gave me this interesting feeling.

"I am very excited that you decided to wear them and listen to me Matt. For that reason, I got you a gift!" I could see how thrilled he was getting. I also think he was feeding off me being so awkward and embarrassed.

"You got me a gift?" I replied.

"Oh yeah I did...you are going to love it. Catching you wearing your girlfriend's panties and calling you out was a lot of fun...but you choosing to put them on and come over here after I told you to do it is a whole different thing." His big smile starts to shift into an evil grin. "So my thinking is that if you are already wearing a thong, you might as well go all out..."

I was confused by what he meant. A present? Go all out? I had no clue at the time what he was getting at.

"What do you mean? What it is?" I asked.

"You will see. Your gift is in a bag in my room...you will see it right when you walk in. You will understand once you open it."

What is happening right now? Why am I playing along with his games? Is it because I am scared he will tell my roommates or is it because maybe a tiny part of me was curious? I walk into his room and see the bag on his bed. I grab the bag and begin to look inside and that's when I really started to panic...

Inside the bag was a black mini skirt, a grey tube-top type shirt and a white lacy padded bra. Like what the fuck! There is zero chance he expects me to actually put this on. I am not about to dress up as a girl for him. He can't be serious! I start pacing around the room trying to figure out how to get myself out of this situation but then I hear Greg knock on the door and say.

"Matttt, its already been a few minutes. I assume by now you have open your little present. Look man, I just think it will be funny to see you dressed up. I promise this will all stay between us as long as you follow through with it. You already were curious about wearing a thong, why not try a full outfit too? It will be fun."

This was not the type of fun I ever wanted to have but did he have a point? I did put that thong on and check myself out in the mirror. It did feel nice and interesting wearing it. I look down at the outfit and in that moment decided I didn't really have a choice.

I stripped down to just the thong and began putting everything on starting with the bra, shirt then skirt. I was shaking a little bit as I dressed myself somewhat mad at myself for getting myself into this situation. I turned and looked in his mirror and was blown away by my reflection. Its going to sound crazy but besides my face, I looked like a girl that I would normally go for. I had never been a big tits guy; also thought of them as a bonus so that wasn't a problem. Tight small shirt, short little skirt, big butt with sexy lingerie underneath. I was so confused by the thoughts that started to pop up into my head. I turned sideways and lifted the back on the skirt up to see my ass in the thong. My mind was mainly focused on the embarrassment of walking out the door like this but a tiny part of me thought 'I actually look kind of hot.'

That thought quickly faded when I walked out of the room and turned the corner to see Greg sitting on the couch waiting for me. His eyes lit up and he instantly starting laughing as he jumped up from the couch.

"HAHAHAHA yes! OMG look at you! Damnnnnn Matt you look so good hahahaha"

He walked over to me and was checking me out head to toe. I felt so humiliated.

"I knew you would want to put it on! The clothes actually fit too! HAHAHA this is way too good! Looks like you grew small little boobies while you were in there too."

I stood there pretty frozen. Here I was dressed up like a college girl standing in front of my gay neighbor and he is loving every second of it. I tried not to make eye contact with him and continued to look down at the ground.

"You have to admit Matt...you look pretty damn hot." He stepped closer to me.

"I look ridiculous" I replied.

"Ridiculously good! Hahaha I still can't get over that you are actually wearing all this but I am soooo happy you are." He places his hand on my shoulder and slowly slides it down my back then out of nowhere slaps my ass.

THWAP! That slap gave me chills and made me jump a little bit. Its hard for me to explain or even admit but in that moment I felt a little girly. I tried to shut it down in my mind but then I felt a little twitch inside the front of my skirt. No way...that couldn't have excited me. What is going on? This is not okay.

"Let's see how that ass looks again. I would be lying to you if I haven't thought about it swallowing up your girlfriends thong!" He is already standing behind me and he reaches for the bottom of the skirt to pull it up but I panic and step forward a little bit to avoid it.

"Greg really? I showed you I was wearing it and I put this outfit on for you. I think that is enough for tonight." YES I made a stand I thought to myself.

"Okay that's fine." He replied. "I will just have to tell our mutual friends about your little secret then.."

I couldn't believe his response. I started to stutter. "Um...b-b-ut." He cut me off.

"Listen Matt, I am your friend and I would never do anything to hurt you and the last thing I want to do is blow up your spot. BUT you are already dressed up and you aren't really in a position to argue. I am just teasing and having some fun with you but its your choice."

He was sadly right...what choice did I actually have? I was in complete shock and awe. I thought about it for a few moments.

"Ok-k-kay..." I said.

He laughs. "I mean I figured you would side with me. Now let me see that ass baby."

He steps back behind me and grabs the skirt and slowly pulls it up revealing my ass in the thong. I feel the draft of his fan hit my ass. He is taller than me so I could just feel his presence behind me.

"Dayum! That ass looks even better than before!"

I feel his hand grab my ass and squeeze it a few times. Each time he squeezed it, he would shake my ass cheek to watch it jiggle. He then started just rubbing his hand all over my ass, feeling the thong and tugging at the material. In that moment, I felt this rush pass through my body. He was clearly enjoying himself which in a way felt good? I know how that sounds but I can't lie. He was looking at me and playing with me like I would with a girl I was hooking up with but in this situation, I was on the receiving end! I thought about grabbing my girlfriends ass and feeling her thong and how much that turns me on. I know how turned on and sexy she gets when I do that to her...was it that crazy I slightly felt that way as well? I didn't know what to say or how to react.

"Mhhh Matt I keep saying it but you do really have a nice girly ass. The thong fits you so well. I don't think you realize how sexy this looks."

He continued to run his hand all over my ass. Tracing the sides of the thong, running his fingers up my crack over the thong and flicking the bottom of my cheeks to make them bounce. I stand there freaking out on the inside. His touch and comments are starting to get to me. I feel the front of my thong and skirt get tighter as my soft dick slowly turns into a semi. This can't be happening. How the hell am I getting turned on by this?

I feel Greg grab the back of my thong pretty hard but only lightly tugs for a quick second holding it a few inches higher.

I shout out. "Shit please don't, not a wedgie again!"

Greg laughs. "What?! Too bad!"

He pulls pretty hard until the thong reaches my middle back. My body is forced to bend forward as he pulls. The sensation of the thong shooting up my ass at the same time it tightens around my balls is driving my crazy. I feel myself squirming around trying not to give into that feeling. Greg sees me squirming and lets out a laugh. He starts to release the thong and I start to stand back up straight but then catches me off guard and pulls another time.

I don't know what came over me but lost in the moment I let out a little moan...

"Ughhh.." Fuck I hope he didn't hear that.

Greg holds the thong firmly and asks me, "Oh Matt what was that?!?"

"Nothing." I say back. "You just caught me off guard, that's all."

"No no no that was a moan. Omg did that feel good? Did you like that? Mhhhh now this got a little more interesting."

I couldn't believe I let out a moan and now I am dreading that he actually heard me! I say again...WHAT THE HELL IS GOING ON?! Why did I let this happen? More importantly, why am I not hating this?"

Greg laughs as he slowly starts to pull again. "Did you really just moan from receiving a thong wedgie? I think you should moan again but this time a little louder."

I am physically and mentally struggling with everything that is happening. I feel him pull the thong even higher almost to my shoulders. The thong shooting up my ass causing me to lean forward heavily again. I have a wonder for a second if this is what it feels like when I bend my girlfriend over. Powerless and helpless.

"Come on Matty, give me one more moan hahaha that was too funny. It clearly felt good. Do it"

He pulls the thong higher reaching my shoulders. The front of the thong is so tight against my ball and I suddenly feel semi flop out from the material and hang hidden in the skirt. Why does this feel good? Why am I liking it? I begin to open my mouth and just decide to commit.

"Uggghhhh" I let out a second moan.

"Mhhh haha yes Matt yesss! I knew you would give in hahaha this is so awesome!" He snickers. "But now...time for the FINALE!"

He uses the hand giving me a wedgie to pull me closer to him by the thong. My back hits his chest and I feel my ass back into his crotch. At the same time, he reaches his left hand around me and under the skirt and grabs my hard cock!

"GREG WHAT THE FUCK ARE THE DOING?!?!" I yell out.

"HAHAHA look how hard you get all dressed up and being teased! You love this, just admit it at this point! You really think I didn't notice your erection a couple days ago in your room!? I just wanted to get you all dressed up and confirm you actually love this before I acted on it!"

He continues to give me a wedgie while he begins to stroke my cock.

I felt so helpless and ashamed. I am not gay...I don't want this...but why does it feel good?! I tried to pull away but he was still holding the thong and I couldn't go anywhere. Feeling the thong shoot up my ass and my cock being stroked was unbearable. I was so confused about what was happening but I couldn't do anything about it. I felt him hunched over me and heard him laughing and then he leans in and says in my ear.

"Damnn you are so hard! Just give in Matt. You clearly love this and its so hot. Just let it happen." He loosens up the grip on the thong but starts jerking me off faster.

My head is spinning! Is my gay neighbor really jerking me off?! I stand there dressed up like a slutty college girl getting wedgied in a thong while getting jerked off.

"P-P-Pleaseee....s-s-s-toppp...d-d-don't..."

About 10 seconds go by and I already feel the pressure build up in the tip of penis. I struggle one last time trying to break free but he has me where he wants me.

"Greg! Pleaseeee s-s-stoppp!"

He just laughs it off and grips my dick harder and speeds up. Hearing him laugh in my ear, the thong in my ass crack and feeling the whole outfit on me just sends me over the end. I start frantically start shooting hot thick cum all over his floor.

"HAHAHAHA yes! OMG you are cumming already?! I don't even think that was 30 seconds! You liked this way more than I thought you would. I knew once I caught you in this thong that I could push you even further!

He continues to jerk me off but slows down the pace as I make a complete mess on his floor. He lets go off the thong snapping it back into place and places his hand on my ass squeezing my cheeks as I continue to cum. He places his head over my shoulders so he can watch my cum shoot out of my dick. I feel so ashamed and gross. I didn't want this! Why did I cum so quick? Why is he doing this to me?

"Ahhhhhhh" I can't help but let out another moan as I stop climaxing.

He starts cracking up as he lets go off my dick and cups my balls and squeezes them. His other hand is feeling all over my ass.

"Wow look at the puddle on my floor. I think I just completely drained you. I bet you no one has ever made you cum like that."

He lets go off my balls and ass. My body feels so weak. My knees buckle and I kind of drop to the floor in shame. What does this say about me? What does he think of me now? I try to catch my breath and come up with an explanation for myself. He walks around me and stand in front of me with a big smile on his face.

"I don't think you realize how hot that was Matt. You looked so good when you walked out and when I heard you moan, I couldn't help myself. I know you aren't ready to admit it but you clearly enjoyed yourself too."

I am still speechless. I begin to stand up. I can't believe what just happened. I finally am able to say something.

"Can I change back now please?"

"Haha of course Matt I think playtime is over for tonight." He chuckles.

Playtime is over for tonight? Those words echoed throughout my head and sent chills down my spine as I walk back into his room. I take off the outfit as quick as I can. Why did I let it go this far? I decide to keep the thong on because I did not wear boxers and briefs over them and put back on my clothes. I walk to the mirror and try to give myself a pep talk attempting to gather my thoughts. I walk back out and Greg is on his couch watching TV.

"Well okay...I am out of here. Have a good night Greg." I say as I walk towards the door.

"Wait! Matt you aren't going to hug it out after what just happened?! I am still your friend man I was just going with the flow. You looked so hot I couldn't help myself."

He stands up and walks over to me and gives me a big hug. I hug him back but then I feel him squeeze me tighter as one of his hands wanders down my back and into the back of the sweatpants grabbing my ass.

"HAHAHA for some reason I knew you would still be wearing them! I had to check for myself. That's a good girl hahaha!"

He squeezes and feels every inch of the thong on my ass. The courage I mustered up back in the room has completely shattered. That's a good girl? What the fuck! Why am I letting this comments fly? Oh I know why...he just made me cum while giving me a wedgie while I was dressed up like a slut. I don't know what to do. I keep hugging him as he touches my ass then he looks me in the eyes and says.

"You can go back home but I want you to admit you had fun Matt."

Fun? This was not fun. I feel tricked and used. Part of me clearly enjoyed it but I can't even comprehend those thoughts yet. I look back at him and nod hoping that's enough.

"No no no you gotta say it Matt haha"

He grips the back of the thong and lightly gives it a tug to warn me what is coming if I don't say it.