The Sikly Red Panties By CDKylie
This story is part fiction and part true.
My name is Kyle, and I'll never forget how much my life changed in my early college years.
As an 18 year old boy traveled about a 2 hour drive north to begin my post secondary education, I was excited about all the future held for me. It was the fall of 2004. Although I had moved away from New England when I was 14, I was an avid Red Sox fan in for the best fall I could ever imagine. All sports fans know how it went. I was on top of the world!
With that, my social life was outstanding, and the woman I started dating in High School had all of my heart, even with the distance between us. She still had one last year of High School to complete, so her and I were only able to see eachother every other weekend. Still though, things were nearly perfect for the first time in a long time.
As time went on, that year began to fly by. My girl friend Kayla and I enjoyed a lot of time together during my winter break. Our sex life was only getting better, although I always felt like I may have been a little too small for her. I was only about 4.5 inches hard, but She was my first just a year prior. Although she never mentioned the size as an issue.
After returning to campus in late January, 2005, things between Kayla and I started to change. She informed me she was going on a trip to Europe with some of her class mates in her high school, and was thrilled about it. I on the other hand wasn't excited that I wouldn't be able to see her during my spring break.
She had the time of her life, while I only heard from her three, maybe four times in the 2 weeks she was gone. Much different than the nightly conversations I used to have with her. While she was gone though, I just started getting this gut feeling that things were about to go bad.
Unfortunately for me, that was indeed the case. I will never know what happened to her over there in Italy and France, but Ill never forget how things felt like they were coming apart quickly. The day she told me she was going to her senior prom with a different guy, I knew I was done for. She had some coy excuse like he was a lonely friend, but I didn't buy it. Two days later we broke up. In all honesty it was the hardest thing I have ever gone through in my life. I felt sick to my stomach for weeks on end. That summer came and went before I started to feel better.
With the new school year approacing I was excited to try to get back into the dating game, but I was stii stuck in a rut. I couldn't bring my self to ask any other women out. As that second year went on my college roommate left mid year, and I was left with the dorm to my self. That alone is probably what led me to where I am today.
I remember sitting at my computer desk one evening watching porn, and stumbling across a website all about men who wear panties. It was thrilling to me. I chatted with other members of the website, and soon found it amazingly arroused at the thought of wearing panties for another man. One afternoon I was in the chat when another man proposed phone sex to me. I agreed, but wanted to really be wearing panties when it happened. I got up the nerve to drive to wal mart and purchase my own panties there. It was very tough, I was sooo nervous, it felt like people could tell that those pink and purple silky panties were for me.
I got to the register, and made my purchase while keeping my head down in my cell phone like I was texting. Hoping the cashier wouldnt notice my flushed face, and hoping I wouldnt see anyone I knew while there. She read me the price, I quickly handed her cash to complete our transaction and took off. I was excited to get back to campus and try on my first pair of panties in my life.
Well, needless to say the feeling was amazing. When the man from Minnesota who I had met on the chat had called me, I was so nervous and excited all at the same time. That man was great with his words. He called me bad for wearing panties, panties were for girls, and told me I must be a sissy boy. He discribed how he would want me to rub his big cock, and eventually take it deep in my mouth. I had really never had any feelings towards sex with other men, but the thought of my wearing pretty panties and having his cock sliding in and out of my mouth drove me to a very intense orgasm. After hanging up the phone I thought to my self: Wow, that was just amazing.
I would go on to spend the next couple of years further exploring my new found love of wearing panties. I eventually was able to connect with an older man on craigslist. He was quite older than I was. About 68 years old. I found that experience quite exciting, and a bit of a learning process. I didnt get the chance to suck cock, or have my virginity taken. As he was older, I found he had ED. Either way, I had a great time kissing him, letting him feel my chest, and modeling different panties for him. He and I both enjoyed it, and eventually both got off onto eachother.
That first expierence was quite the thrill for me, but I felt like I wanted more. I wanted to try sucking cock, and I really wanted to be penetrated. I had practiced with dildos that I purcahsed that previous summer, but I wanted the real thing. As time went on I tried countless times to meet a good man on craigslist, but had so many people either flake out on me, werent looking for what I was, or we just didnt seem to hit it off. Finding a real man was going to be more difficult that I had imagined.
Two years went by with out any luck of finding what I really wanted. I knew I needed to stop worrying about it, and see if it would eventually work it self out. After college I started working at a local telecom company. At this point I was 23 years old, and would wear panties on a pretty regular basis, sometimes even to work. It was such a sexual thrill to be wearing cute panties in public, with out anyone really knowing! I remember one day specifically because it was the first time I had worn red panties to work. They were high cut silk bikini panties with a cute flower emblem on the front. I went through that whole day of work wondering if maybe I slipped up. Perhaps I bent over too far, or my shirt rode up in my chair. I disreguarded it that night, and thought really nothing more of it after that.
About 4 days later I remember one of my co workers coming up to me and talking to me while I was between calls. His name was Tim. He was a guy I had seen in meetings from time to time, but was kind of quiet. I remember being surprised that he stopped to talk to me. He was the kind of guy that had the looks that I really liked. He was older, probably early 50's, salt and pepper hair, about 6 feet tall, and 240lbs probably.
After our first conversation I didnt have any kind of suspicion about it, just figured he was wanted to chat. However, Tim starting talking to me more and more. Even would seem to end up on lunch break with me most days. One evening at work he came over to talk to me, as I had just missed a few days with a chest infection. He saw I was talking to our boss, and wanted to make sure I wasnt getting written up or fired for my absenses. I explained to him everything was fine, but he still gave me his number incase so I could keep in touch with him.
At that point, I was very excited to have his number, I wanted nothing more than for him to have his way with me, but never knew how to approach it. So, that Thursday I knew we both had that day off, and decided to give him a call. He asked if I wanted to go out for a drink, and I graciously accepted. Told him to give me about half an hour to get ready. He got my address and said he would pick me up then.
I was so excited I bolted into the bathroom to quickly shower. I also shaved my pubic area, (although I did that frequently anyway) and took some hair trimmers to my legs as well. I wanted to be smooth, with out looking like I did too much! I decided to wear my silky red panties again, incase anything happened.
While at the bar we talked about pretty basic boring things. The weather, baseball, and of course, work. I could feel a tension between us, but neither of us said anything. As it got later he asked if I wanted to go back to his place to hang out more, and finish watching the baseball game. I happily agreed. While driving I could see his face wanting to say something. I was dieing inside hoping to hear him tell me he was into me. I wanted so bad to say someting too, but kept my lips sealed. Once we got inside he offered me a drink, I agreed, and he asked me to grab a couple of cups. They were in the top of the cabinent to the upper left corner. Not a super easy grab, and only being 5'9 made the reach a little tougher, but I noticed he watched me closely as I began to reach. In my head I was thinking that if I wasnt careful my panties would show a little. I figured that was probably the best thing to do, and reached real far back for a couple of glasses.
I knew he saw my panties, I figured the ball was in his court now to make mention of it. Once I sat on the couch, he came and sat right next to me. A few second later he finally said something!
"Kyle, I dont mean to be too personal, but when you reached up for the glasses I saw your shirt come up a little, and I saw you were wearing red panties."
I had knots in my stomach after he said it, and I was so happy at the same time. Now I just had to hope he was into that. I told him "oh, yeah. I hope it doesn't bother you, I have been wearing panties for a few years now." He was intregued, and we continued to talk more and more about it. He told me it didnt bother him at all that I wore panties, and he actually thought it was kind of hot. Things from there got more and more personal. He told me the reason he invited me out is because he saw I was wearing panties at work one day, but didnt know how to approach it.
I told him I started to get that feeling when he started talking to me, and told him how excited I was because I thought he was very sexy. He then started to rub my thigh. I moved closer so he could feel more. I was wearing some nylon gym pants that I usually wore either working out or running. They were quite comfortable, and perfect for the situation I found my self in with Tim.
He then leaned in and kissed me, and at that point I started to lose control. I went right in and locked my lips against his. It turned into a passionate make out, with his hands now rubbing the front of my panties through the pants. I reached down to try to feel his cock through his pale blue jeans, and felt a big thick cock through those jeans.
He invited me to his bedroom, and guided me there. He stood behind me, and directed me where to go. When we entered the room he closed the door, and flicked the light switch that turned on a small lamp next to his bed. Once in the room he reached down to my hips and pulled me back into him and began kissing my neck. His hand wandered up my shirt, felt my chest, then ran his hands down to my pants, where he slid his hand in and began caressing the front of my red silk panties. I was very hard already, and couldnt believe what was happening. He then slide the pants off, and began grabbing and rubbing my panty covered ass.
Tim then walked in front of me, where I was able to grab the front of his jeans, and began working them off of him. I slid them down, and he took his shirt off leaving just a large bulge in his dark bluebriefs. I knealed down in front of him and he lift my shirt over my head. I then began foldling that hard cock through the briefs, and then let my hands pull down the wasteband just enough for the head of his cock to pop out. I began lightly touching the head of his cock with my left hand, and used my right hand to caress his balls through the breifs. He let out a deep moan as I slid my left hand deeper and deeper into his breifs.
Shortly after I slid the briefs down completely, and let him step out of them, which left his thick hard cock right in front of my face. It was a little intimidating, I had never tried this, and there was Tim's 7.5 inch cock sitting in front of me. It looked as though it was close to 1.5 inches thick too. Although I had felt nervous about doing a bad job, I decided it was my destiny, and it was time for me to become the cock sucking sissy that I felt inside of me. I just opened my mouth wide and slowly began taking him in. I worked my way down and he began encouraging me, while calling me a feminine name. "Mmm good job Kylie, take more of that cock in your mouth sweetie I know you can." I did as he asked, and slide about 4.5 inches in, and began to feel it getting closer to the back of my throat. I knew I had to try to beat my gag reflex. and I just kept letting his cock move a little more each time. I had read online that it was helpful to try to have a dick go to one side or the other when taking it deep in the mouth, and that tip helped a lot. I was able to get about 5 to 5.5 inches of Tim's thick cock into my mouth, and sucked him for a good 10 minutes when he pulled my head up and told me he wasnt ready to cum just yet.
Tim then brought me up to my feet and turned me around and layed me onto his bed. Still wearing just the silky bikini cut red panties, he crawled in next to me and began kissing me once again while rubbing the front of my panties, where were getting wet with my pre cum. I remember him saying "hmm you must really like sucking cock, your panties are getting wet..." Just him saying that drove me wild. He then began sliding his fingers into my panties, first rubbing my small but hard cock, then he cupped my balls wit his hand, and started pressing his middle finger against my sissy pussy. While we continued to make out he slid and pushed his middle finger harder until he was inside of me. He gently began sliding his finger in and out of me, leaving me feeling like I was in heaven.
He asked me if I had ever been fucked before, I told him no... he asked if I would mind him taking my virginity. I nervously agreed with a big smile on my face. He then grabbed some lube from his night stand, and began rubbing it into my tight sissy pussy. I asked him if he would mind if I kept my panties on while he fucked me. He said "Absolutly, I love to fuck you in those sexy red panties." His words were enough to nearly make me want to cum right then and there, but I held back, I wanted to be penetrated in the worst way. He then pulled me down to the end of his bed while I was laying on my back. He slid the crotch of my panties over a little bit, and began pressing his big cock into me. It was difficut for him to get in, Although I practiced with dildos getting in was tough sometimes. He kept pressing and pressing when I finally felt him push through. Once he was in he began pressing in further, and started thrusting in and out slowly at first. I didn't really feel any pain after he got inside of me. The first push was the only pain I really felt, and after that it started to feel amazing. After a couple minutes of slow short thrusts, Tim begain longer deeper thrusts into my tight sissy pussy. I just lied there staring up at his face when he asked me how it felt.
Tim: How does that cock feel baby? Me: Ohh god it feels so good Tim Tim: That wet spot on your panties is getting bigger.. Me: Im so wet for you..
Tim: You feel so tight, your such a good sissy, taking my cock so deep. Me: (while moaning) ohh your cock is so amazing..
Tim began thrusting harder and harder, I felt an incredible pressure feeling like I was about to cum, instead of fighting that feeling I just kept taking his cock deep, and felt my self shoot cum all over the inside of my pretty red panties. Those panties were soaked. He then slowed down and asked me to get on all fours. I flipped over for him, and Tim re entered me from behind. His cock went right back to pounding my sissy pussy. the feeling was so incredible. Tim continued to talk dirty to me:
Tim: (Slaps my panty covered ass) Are you my good little sissy slut? Me: (moaning loudly) ohhh my god YES, I am all yours, I am your sissy! Tim: You want me to cum inside of you my little sissy? Me: (still moaning) yes, I want your cum, I want your cum in me! Tim: Youre such a naughty gurl..
His thrusts continued to pick up pace, and I began feeling his cock swell up inside of me before I heard him let out a loud grunt, and then felt ropes of cum shooting out of his cock and hitting me deep inside. He thrusted another couple dozen times before he was empty..
I rolled back over, with the front of my panties still covered in my cum, and Tim's cum leaking out into the back of my panties...
More to come later!