I let myself get caught masturbating

I’ve often fantasized about getting caught while masturbating and on a recent vacation to a Jamaican resort I had the ideal opportunity to let it happen. On the fourth day at the resort as I was sitting by the pool enjoying the “sights” I started feeling the desire for some sexual gratification. Since my wife was in the pool doing water aerobics I decided to go back to the room to relieve my desires with some quick solo pleasure. As I neared the room I saw the “housekeeping” cart at the room next to ours and when I went inside our bed was still unmade. I assumed that the maid would most likely be coming to our room next and since I was already planning to masturbate, the thought of “getting caught” came to mind. I was immediately turned on by the idea but I wanted to do something so that it didn’t look too obvious. I figured the best thing would be to make it appear to the maid that I didn’t hear her knock on the door. I got my ipod and earphones out of my bag then removed my t-shirt and bathing suit and laid on the bed in direct view of the door. My cock was already hard and fully erect as I put the earphones in place. I then put the ipod next to me for show but didn’t turn it on so that I could hear when the maid was coming. I was beginning to feel nervous about what I was doing but by then I was so turned on that I didn’t want to stop. As I began to slowly rub my cock and think about the maid seeing me I realized I wasn’t going to last very long. I then heard the cart in the hallway moving closer. My heart really started pounding as I wrapped my hand around my cock and began stroking my erection. When the maid knocked on the door and said “housekeeping” I shut my eyes enough so they appeared closed but I could still see through my eyelashes. I then began to rapidly stroke my hard pink meat and as the maid unlocked the door my balls tightened and I felt that familiar pulsing sensation in my very excited cock. Even if I had wanted to, I knew there was no way to stop myself from cumming and as the door opened a stream of cum shot on my chest and belly. The young maid appeared to be totally surprised and immediately began to apologize for coming in but as I continued stroking my cock and squirting cum on my belly she seemed to sense that I didn’t know she was there. She then left the room and quietly closed the door behind her. I opened my eyes and watched the last bit of cum drain onto by belly as I finished stroking my cock. I could hardly believe I had just let someone see me masturbating but the large amount of cum on my chest and belly made it pretty obvious how excited I had been. I used several tissues cleaning up my cum then tossed them into the waste basket. There was no doubt in my mind when the maid emptied it a short while later the smell of cum was still noticeable enough to remind her of what she saw.

I'm still a Sissy

It's a new year but nothing has changed. I'M STILL A SISSY wearing my panties 24/7 and masturbating while I fantasize about sucking cock! I hope in the new year I will once again enjoy the pleasure of having a cock in my mouth! I want to suck cock and I want to swallow a nice big load of another man's cum. My cock gets hard whenever I think about it and I've been thinking about it a lot lately. I have a hard cock in my panties right now that is begging for pleasure and I'm about to take care of it. It will be my first masturbation session of the new year and I'm sure there will be many more to come. It's time to play!

my usual Friday, I'm masturbating

It’s my usual Friday…my wife is at work and I’m at home “enjoying” myself. I am so horny after looking at pictures on Flickr, especially other sissies in their panties sucking cocks. What lucky sissies! I wish I could be doing that right now. I would love having a big cock in my mouth, filling it with a hot thick creamy load of cum! Mmmmm, that sounds so good! I have my silky panties on and I’m playing with my cock. My god I love to masturbate! It gives me such pleasure. Over the past two weeks I had two masturbation sessions that were incredible. Both times I ended up on my back with my legs up on the wall and my cock pointing straight at my waiting mouth. I really enjoyed the big loads of cum that I shot in my mouth and all over my face. I really get turned on doing that and I’m ready to do it again! My cock is so hard! I’ve been playing with it all morning and now I’m ready to taste my load. Oh wow, I just about lost control in my panties thinking about cumming into my own mouth. My cock and my mouth are both very anxious. AND I CAN’T WAIT ANY LONGER!!!

My third try was the charm....

It took almost eight years after the last time that I had an opportunity to fulfill my sissy desires before I got the chance again. Even after getting married I couldn’t stop thinking about sucking cock and I continued to discreetly search for someone to help me fulfill my desires. Over the past eight years I communicated with at least a half dozen men that lived nearby but nothing ever came from it. With being married the opportunities were hard to come by. I finally found a man that was interested and being understanding of my issues, he didn’t push things but said when I was comfortable he’d be ready. It took almost nine months from our first communication before everything seemed right. We made arrangements to meet but when the day arrived I contacted him with an excuse. Afterwards I was upset with myself for backing out once again and decided I either needed to “do it” or stop having the desire. I knew it had to be the former so after three weeks we again made arrangements to meet.

I put on a pink bra and panties then nervously drove to the sleezy motel where we had planned to meet. I could hardly believe what I was doing when I actually knocked on the room door and went inside. I had told him prior to meeting that we would need to “start in” right away before I had an opportunity to back out. He took control as soon as I entered, making me remove my clothes and “model” my sissy undies for him. He then made me strip him and when I didn't fold his clothes neatly after removing them, he spanked my butt. And then the moment I had been waiting almost ten years for finally happened! He told me to get down on my knees and welcome him to town. I knelt down and started to lick his cock then slid it in my mouth. Oh my god, it was so incredible! I HAD A COCK IN MY MOUTH!!! It was thick and smooth, and felt so big in my mouth. I was very nervous but loving the moment. We spent about an hour and a half together with me being submissive and him giving orders. I had my butt spanked several times and spent a lot of time licking and sucking his cock. I've always fantasized about swallowing a big load of cum although it never happened that day. I wasn’t certain whether I could really do it or not but I didn’t get the chance to find out. I hope it will happen in time. That was my initiation and I was happy and excited to have finally accomplished the first step. I can now honestly say, I know the feeling of having a thick seven inch cock in my mouth and it was wonderful!!! My mouth is no longer a virgin, it was filled with cock and I can now proclaim, I am a sissy cocksucker! That can never change for the rest of my life. No matter what else happens, I will never have my virginity again. I've SUCKED A COCK!!!

After discovering my sissy desires......

For the next few months after discovering my sissy desires I masturbated often while viewing pictures of other men masturbating or sucking cocks. Occasionally I would still masturbate while looking at women in panties but nothing excited me more then looking at a man with an excited cock. My fantasies almost always involved playing with or sucking another man’s cock and I soon realized I had the desire to have a sexual experience with a male. I placed a free ad at a gay personals web site expressing my desire to masturbate with another man with my ultimate desire being to suck their cock. It was much more difficult to find someone then I expected it to be and although I corresponded with several men in my area, I only got comfortable enough over a two year time span to meet two of them. I met the first man at a bar for a few drinks. He was “very” gay and looking for a “mutually” fun time. After talking for an hour we went our separate ways that night and even though we corresponded occasionally after our meeting we never got together again. As I continued in my search for someone to help me fulfill my desires, I came to the realization that I wasn’t interested in mutual fun with a man or reciprocation but rather that I wanted to be totally submissive to a dominant man. I wanted to be told to “suck my cock sissy” and made to masturbate in front of him for his amusement. The second man that I met seemed to fit that description. He knew beforehand that I wanted to be a “sissy” and he was turned on by the thought of having a man wearing panties sucking his cock. One evening while I was online he “instant messaged” me as he had on several occasions during the prior weeks. Up to that time I couldn’t get up the nerve to meet and would make up excuses why I couldn't. I had the desire but I couldn't get past my nervousnous. On one particular evening I was really horny when he asked if I wanted to come to his house to suck his “big cock” I couldn’t resist my desires any longer and agreed that it was a good night for him to “fill my mouth with cum”. I put on a clean pair of panties then nervously drove fifteen minutes to his home, fully expecting that by the time I returned to my house that night I would know what it was like to suck a cock. Unfortunately it didn’t turn out that way. The man’s house was dirty and smelled of animal urine and I was turned off from the moment I arrived. The bottom line however is that in the end I got scared. He asked me if I was wearing panties which I told him I was then he asked if I wanted to go into the bedroom and I declined. I can’t believe it, I was so close to fulfilling my desire and I backed out! I was only minutes from tasting cock and a few minutes further from tasting another man’s cum. I was really disappointed for letting the opportunity slip away. A few months later I got married to a woman I had been in a serious relationship with for many years prior to my discovering my sissy desires. It’s unfortunate that I didn’t know my desires sooner in life so I could have explored them further prior to our relationship. Unlike in my first marriage, my current wife does know about my panty fetish and she knows that I wear them daily. She’s okay with it and calls me her little sissy! However, she has no absolutely no idea of my true sissy desires and I’m sure she would never understand them. I live in fear of her finding out as I’m certain she would divorce me. It’s a constant struggle between my love for her and my sexual desire to be a sissy that sucks cocks!

Discovering my sissy desires.........

Even though I’ve been wearing panties 24/7 for a number of years now, it was only about ten years ago when I discovered my true sissy desires. I had been corresponding via e-mail with a woman who was acting as my “domme” and giving me various orders and tasks to “sissify” me. She would have me buy specific panties then send her pictures of me “playing” in them or to make me feel more feminine and smell pretty she would have me take bubble baths. Sometimes she would have me wear a maxi-pad in my panties for a few days and other times she would make me go out in public with a butt plug properly inserted. They were usually very simple tasks that were used to make me feel more effeminate. Then one day I received an e-mail from her that asked if I had ever felt any sexual attraction towards men? I responded that I definitely had not, that my only sexual attraction was for women. She immediately sent me a task to perform saying males that wear female panties usually have female desires also. In order to better understand my female desires Iwas to wear a bra and panties only, then search for websites with pictures of men masturbating either alone of with other men. I was then supposed to masturbate while viewing the pictures and give her a detailed report. Of all the tasks she had given me, this one I truly detested and even considered not doing it then making up my report for her. Although I had no interest in performing the task I decided I would do as I was told so I could tell her how disgusted I was looking at men. I stripped down to just my panties and put on one of my bras then got online to complete my task.

When I started searching I couldn’t believe that I was actually going to masturbate while looking at pictures of men and assumed I would have a hard time even getting an erection. After finding websites as instructed I began viewing various pictures of men playing with their excited cocks. Some were alone and some were with other guys. Most of them had cocks bigger then mine and I was intrigued by their size. I wasn’t paying much attention to the men themselves but focused on their big hard cocks. The only time I focused on the guy himself was usually in the pictures where the man was cumming or had cum. I enjoyed seeing the pleasurable expressions on their faces knowing that I’d shared that same pleasure many times. To my surprise I realized I was getting quite aroused and had already started massaging the erection in my panties. It wasn’t long before I was as turned on as I had ever been in my life. I couldn’t believe it, I was not only looking at other men playing with their cocks, I was masturbating too! I continued rubbing my excited cock through my panties as I viewed more pictures and soon they were wet and sticky with my pre-cum. Most of the websites had the pictures divided by “interests” and up to that point I’d only been looking at “masturbation” pictures but then decided to check out “sucking”. Oh my god, I was looking at pictures of men licking and sucking other men’s cocks, and getting even more turned on then I ever imagined! I had never even been really turned on by seeing pictures of women sucking a cock but seeing one man sucking another man was really hot. I started wondering what it would be like to have a big cock in my mouth then feel it begin that orgasmic throbbing and knowing I was about to have my mouth filled with cum. As I looked at the pictures I was imagining my own mouth and expressions with a cock in my mouth. I finally couldn’t handle the excitement any longer and I wanted my mouth filled with cum.
Since I wasn’t as limber as I had been in my younger days I had found a new method to cum in to my own mouth although my accuracy wasn’t quite as good. I would lay on the floor with my butt as near to a wall as possible then put my feet up on the wall over my head, kind of a sitting position but while laying on my back. I would then inch my feet up the wall until my body was almost fully extended up the wall with my feet flat against the wall, my knees bent, and my back almost against the wall. In this position my cock is about fifteen inches away but it’s directly over my face. I quickly took my panties off then got into position. At that moment there was nothing I desired more then to have my mouth filled with a big excited cock. I was wishing I could suck myself just to see what it felt like to have an excited penis in my mouth. As I looked at my own excited cock pointing directly at my face I couldn’t even believe what I was desiring. I then said aloud to myself “oh yeh, I would really love to have someone’s cock in my mouth, I want to suck a cock so bad. Oh god yes, I want to feel a big hard cock filling my mouth with cum”. I couldn’t control my excitement any longer at the thought of another man shoving his cock deep into my mouth and making me swallow his load. I felt the throbbing sensation in my excited penis and knew I had passed my point of no return. I hadn’t even touched myself for at least a minute and yet I was so turned on by my thoughts that I was starting to cum. I opened my mouth in anticipation then watched as a stream of cum shot from my aroused cock, landing on my chin and in my mouth. Since I was already ejaculating I began rapidly thrusting my hips without stroking myself and my cum was shooting everywhere, on my face, in my mouth, in my hair, on my chest. It was so incredibly exciting! I shot such a big load of cum and it was all over me. When I finished ejaculating I slowly stroked my cock and the last bit of cum dripped into my waiting mouth. I laid there for a moment thinking about what a wild incredible orgasm I had then went into the bathroom and as I looked in the mirror I couldn’t believe the amount of cum I had on me. I’m not sure I had ever cum so much. I began wiping it with my fingers and licking it but then I became disgusted with myself and finished cleaning myself up with a wash rag.

Afterwards I sent an e-mail to my “domme” to give her my detailed report of what I did that night and within fifteen minutes I received a response that read “It sounds to me that my little sissy likes big boy cocks afterall. I’m not surprised! You can try to deny it but it’s obvious from your excitement that even though you proclaim to only have a sexual attraction to females you indeed also like men! I am quite certain it will only be a matter of time until you’re on your knees with a big cock in your mouth and your own cum will be squirting into your pretty panties as you swallow your first load of man cum!!!” I laughed and thought “not a chance in hell” then as I went to bed I dismissed the event as one of the strangest things I’d ever done.

When I awoke the next morning I again thought about the previous night and couldn’t believe I had gotten so turned on looking at sexually aroused men. It definitely was a weird thing for a heterosexual male to do and I wrote it off as a once in a lifetime experience. The trouble was I couldn’t get it out of my head. When I was home from work for lunch that day I couldn’t resist getting on the computer and visiting one of the websites I’d been on the night before. As I quickly looked through the pictures, I found some of a man with his hands tied behind his back being forced to suck a large cock. I realized I again had a full erection in my pants and I was massaging it. I very nearly came in my pants but managed to get myself under control then realized I needed to get back to work. For the rest of the afternoon I already knew what I would be doing when I got home and it was hard to keep my mind focused on my job. As soon as I got home I immediately got back on the same website I had been on earlier that day and before the pictures even appeared I had a boner in my pants. I began massaging my very excited cock through my pants as I viewed the various pictures while fantasizing it was me with my hands tied and being forced to orally pleasure the man’s big thick penis. Within a few minutes I felt that familiar throbbing sensation. I was again past the point of no return I was going to cum in my pants! I didn’t care as it seemed appropriate for a sissy to cum in his pants while looking at a big hard cock and oh my, did I cum! My orgasm was probably as intense as it had been the night before and I soaked the front of my pants with a massive amount of warm sticky cream. Normally after I ejaculate I don’t have much interest in tasting my cum but I was still so turned on that I removed my pants then licked all the sticky semen from inside my panties. I masturbated and ate my cum three more times that night while looking at pictures of men masturbating and sucking cocks. I couldn’t believe it but I had ejaculated more times in a twenty-four hour period then I ever had in my life, and my arousal was from men rather then women.

Becoming more obsessed with feminine underwear...

My first marriage lasted a little over seven years and in all that time my wife never knew about my fetish for wearing panties. After getting divorced I had more time then ever to again enjoy masturbating in panties and I became even more obsessed with female undergarments. In addition to making the occasional fun trips to the store to purchase panties I began ordering them through the mail along with girdles and bras. I then started wearing them under my clothes while doing my grocery shopping and I would always wear my pretty feminine undies while doing any house cleaning chores. After a while I finally decided to wear a pair of panties to work for the first time. I was nervous and wore a pair of my male underwear over them but having the silky material against my skin all day felt wonderful and my “secret” excited me. When I would get home at night I couldn’t wait to relieve my excitement and would soak my panties with a big load of cum. A few times I didn’t wait until I was home. I would begin playing with my excited cock as soon as I would drive out of the parking lot at work and would cum in my pants before getting home. For quite awhile whenever I wore panties to work I would wear my male underwear over them but eventually I got braver and wore only panties. After that it didn’t take long before I also started wearing pantyhose and panty girdles under my clothes. I now wear panties every day everywhere I go and my “secret” still excites me. I work in an office that is comprised of mostly females who are unsuspecting that their boss is wearing the same type of silky sexy undergarments that they are wearing. I love being as “girly” as they are.

I don’t know why but I really enjoyed the times driving home from work when I would get myself so aroused that I would cum in my panties. It probably sounds weird but I then started thinking it would be fun to discreetly do the same thing in public places. I started with something very easy, the drive up window at the bank. I had been playing with my cock at home and continued to play with it as I drove to the bank. By the time I arrived at the bank I was incredibly aroused and pulled up to the window with a very hard cock in the silky panties I was wearing under my pants. The pretty young woman who I had dealt with on numerous occasions before greeted me as I placed my items in the sliding tray. She began “working” the transactions and chatting with me at the same time. I was thinking about how she was maybe six feet away with only a window separating us, and she had no idea that I was sitting there wearing panties and with a very excited cock. I was driving a van so I was sitting at pretty much the same level as her and as we talked there was no way for her to see that I had placed my hand between my legs and was rapidly rubbing my erection. I was so aroused that after only about ten seconds I felt the wonderful throbbing sensation that precedes ejaculation. Whenever I get that feeling I know that I’m beyond my point of no return. I was about to cum in my panties and couldn’t stop if I wanted to! With the young woman still talking to me I felt several streams of warm cum squirting into my panties and totally soaking them. It was the most enjoyable banking I’d ever experienced and I repeated that same scenario many more times after that.

After making myself cum in my panties at the bank I also did it a few times at fast food restaurant drive-up windows although it usually was a little more rushed and didn’t seem quite as enjoyable. After a while I had the desire to be a little more daring and decided I was going to cum in my pants while in a store (prior to all the surveillance camera’s in use now). For my first attempt I went to a smaller local department store and wore cotton panties to give myself a little more protection. Just like at the drive-up windows I got myself thoroughly aroused before arriving at the store and as I walked inside, if anyone would have seen me they would have probably noticed I had an obvious erection in my pants. I immediately went to where the lingerie was located, placed my hand in my pocket then rapidly rubbed my cock. Within seconds I shot a big warm load of cum into my panties. A wet spot very quickly appeared in my jeans so I walked out as quickly as possible. While it was fun, it wasn’t nearly as enjoyable as it was at the bank. I did the same thing a few more times at other stores but it didn’t have the same thrill as being in the presence of an unknowing female at a drive-up window.

I still really enjoy the feeling of shooting cum in my panties although it’s been several years now since I did it in any type of public setting. I’m not sure why I enjoy it so much but I do! There’s nothing better then reaching that moment of excitement where you’ve lost control and suddenly realize “I’m going to cum in my pants”!!!