You’ve heard this all before, the guy that finds his Sister’s or Mother’s underwear. For me, it was very similar, we had a neighbor family that moved out of state, they had more boxes than room in the moving truck, we had a spare room, and they had agreed to arrange for the boxes to be shipped once they settled into their new home in Colorado. So we had these boxes, eight of them stacked in a room for months.
Finally, the family had contacted us and advised the boxes we had been storing were just clothes that may as well be donated locally, as the cost of shipping all of them would be more than the contents were worth. Naturally, I was given the task of hauling the boxes to one of the nearby clothing donation collection containers. I found that the boxes were too large to stuff into the container, and so I began opening the boxes and putting the clothes into the container. It didn’t take long before I started seeing women’s panties, and bras.
I took hold of one of the bras, it was flesh-colored and lacy, wow, it felt great, and I realized I had a raging hard-on. I put the bra back into the box and kept feeding the other clothes into the container. I found a matching pair of panties and several more sets that all looked very sexy. They all were set off to the side, and by the time I had donated the rest of the clothes, I had three matching sets and a burning need to get home and more closely familiarize myself with these dainty things that were causing my dick to strain painfully against my jeans.
Suffice to say that later that night in my room, started the first, of countless sessions that involved slipping into a bra and panties, admiring myself in the mirror on the wall, and ending with my throbbing cock spurting hot jizz onto my stomach.
I can’t explain why I was doing this, I’m straight and like every other guy, I constantly had sex on my mind. Maybe it was because I didn’t have much experience, sexually speaking. I know I would certainly have preferred that not to be the case, and the few encounters I did have, were good, well.. awkward.. but good. However none of those encounters included partners that wore such sexy underwear, this was the first time I had ever actually touched these lacy treasures, and now I owned several sets to choose from.
I couldn’t explain my actions though, 99% of the time, all I could think of was getting laid. But that other tiny percent, I wanted to be the object of my own desires. While dressed, I felt so feminine, I wished that I had breasts to fill my bra, stuffing socks into the bra helped, but I wanted cleavage, I wanted to pull on my nipples and see them harden against the delicate material of the bra. I wanted to feel the weight of breasts that would have filled the C-cup, but instead of worrying about the breasts I didn’t have, the one thing I did have, was a fresh load on my smooth tummy, and a good girl would never let that go to waste. The taste of my cum wasn’t what I had expected, it wasn’t bad, but somehow I thought it would taste sweet. I knew that in time, it probably would.
This was my life for several years. My ‘girl time’ increased a bit, but never became an infatuation, I did feel like I needed to expand my horizons a bit tho. One year during the Christmas shopping season, I bought one of those makeup gift sets that included more than any woman could really need, right? I remember the first time I tried to put makeup on ended in me nearly giving up. There was no way I’d be able to make myself look like a woman, makeup was definitely more difficult than I expected and so after watching many youtube videos, and much practice, I could now ‘put on my face’ and actually feel quite sexy. If I had a wig, it would have been difficult to tell I wasn’t a woman standing in front of her mirror in her underwear.
The makeup led to the next phase of my journey. As I mentioned earlier, I never let a load go to waste, but now, with my face all dolled up, I really wanted to blow a load directly onto it. I wanted to look into that mirror and see a faceful of cum slowly dripping down. I accomplished this by assuming uncomfortable positions while madly jerking off, and then trying to aim (often, without a lot of success) to take the facial. There were some occasions though, where it went perfectly, and I looked just like so many of the Porn Actresses at the end of a scene.
I knew at this point I’d need to buy a dildo, a big one, that had big balls.
The problem was, my house situation wasn’t great for having packages delivered and I was too shy to drive up to a sex toy shop and buy a dildo, let alone one like I had planned to purchase. What if someone saw me? I could picture myself handing a thick veiny dildo up to the cashier just as one of my neighbors walked up, recognized me, and would say something like ‘That’s an awfully big cock you’re buying..’
So yeah, no sex toy shops. Finally, I bit the bullet and just ordered one online, and made sure I watched for the delivery truck, it took nearly a week, and I was worried sick the whole time that someone else would get the package, and I’d end up facing lots of questions about what I had bought, etc etc etc.. But as the truck drove off, and I stood there in the doorway with my package, I couldn’t help but wonder why it felt so heavy.
There was obviously no way I’d be able to wait till later that night to check the contents, so rushed back to my room, locked the door, and got the wrapping and box opened up. I could say I was surprised at the size of the plastic cock that I was now holding in my hands, but that would be an incredible understatement. The dildo looked exactly like the pictures online, only twice the expected size. I had no expectation that I’d be able to get this thing into my mouth, it was just too big, and sorry, but I’m not sending this back and going through that nervous nonsense again.
I wrapped the dildo in some older jeans and put the jeans at the back of the shelf in my closet. I had to figure something out. The rest of the day was spent trying to decide what to do. The dildo was the right length, coming in at a very respectable eight inches, with seven and a half inches ‘insertable’. Except the thickness was something I hadn’t accurately planned for, I really didn’t think I could open my jaws enough to get that thing in my mouth. All of my plans to cum on the dildo, and then lick the jizz off, or wrap my lips around it and suck it clean, seemed as if it would be impossible.
Later that night, I locked my door once again, and began the ritual, carefully applying my makeup. I wore dark red lipstick, I wanted to leave my mark on ‘my Lover’s cock’. I took my time and made sure I did the best I could manage, I felt like this would be how a woman would be, taking the extra time to freshen up and look that bit sexier for her Lover who would be waiting in the bedroom. My Lover, on the other hand, was a gigantic plastic cock that would soon be dislocating my jaw while attempting to get past my lips. I put on the black lace panties and bra, tonight was going to be an extra naughty night and the matching black set always felt the sexiest.
I started as I often did, standing in front of the mirror, and feeling my body, caressing my panties and cupping my bra, tracing little circles where my stiff nipples would be. I licked my shiny red lips and began swaying to some unheard music, my eyes were half-closed and I imagined my Lover, laying on the bed, with his hands clasped behind his head, and his cock standing at attention. A cock that looked exactly like the one I had bought, but his twitched slightly until his hand encircled it and slowly began stroking up and down. I made my way over to the bed, and climbed onto it, on all fours moving to where my imaginary Lover would have been laying, and took the dildo into my hand, placing it on the mattress aimed skyward as I licked my lips once again, smiling as I dipped my mouth towards the head..
I began the same way I had seen countless porno scenes, small, delicate licks, coating the cock, until it began to glisten and my patience had all but gone, it was time to see if I could give ‘my Lover’ a blowjob. I kissed the tip of the cock, and slowly moved my head downward, my lips stretching as more of the cock began entering my mouth. my jaw felt uncomfortable, and I felt like that would be the end of that, but the little she-demon on my shoulder whispered ‘don’t give up just yet.’ So I moved back off the cock, licked my lips, and noticed the lipstick left behind on the head. That absolutely caused my own cock to pulsate even more, and so I moved back to my task.
I had seen several scenes where the Actress would allow her tongue to slip past her lip, and glide along the underside of the cock in her mouth. That’s always seemed so sexy to me, and I tried the same now, but things weren’t working as planned, I decided to just keep trying, and within a few seconds, I could feel the head of the cock slip past my lips. It felt like a triumph, but at the same time, my jaw was aching badly, and all I had was the head in my mouth. How in the world are women able to get so much cock in their mouths?
I pulled back off and went back to licking the cock, getting it nice and wet once again, I moved down to the big balls, and began licking those too. I’d gotten the head into my mouth, so I knew it ‘kind of fit’ now I just wanted to see what else I could do with ‘Max’.. that seemed appropriate.. I’d call my dildo Max. I licked along the length, spending extra time at the bottom of the head where it’s most sensitive, flicking my tongue there, lingering, kissing softly before opening my mouth and taking Max back inside. I tried to relax with my mouth opened so wide, but this was new territory, and I couldn’t keep ‘my Lover’ in my mouth for long before I needed another break. I decided I really needed to get off, and I especially wanted Max to get off, so I began sucking on Max’s balls while I stroked myself and within seconds I felt the pressure building and knew I was about to cum. I aimed my cock along the top of Max and fired several long spurts of cum that nearly all landed on their target.
Now it was time to be a good girl and clean Max up, I licked along the shaft, scooping up cum with my tongue then swallowing, smiling to where ‘my Lover’ would have been able to see. I continued licking and wrapped my lips around the head once again, now sucking, urging forth any cum that may yet remain. As I moved my lips off the cock, I gave a final kiss to the tip, then opened my mouth so that Max would have been able to see his cum pooled on my tongue. I closed my mouth, and with the sexiest smile, swallowed deeply. I opened my empty mouth, licked my lips, and then collapsed on the bed.
Like a lot of others, I can feel guilty after cumming, but right now I just felt really sexy, I felt like, if I had been with an actual Lover, they would have really enjoyed my performance. I felt like if that dildo had been a bit smaller, I could have done a much better job, but it might just be that I’d need to practice. This was also about the time I felt like I was probably Bi. It wasn’t anything like a painful discovery, but at that minute, it felt like that whole experience would have been even better with a real cock in my mouth, and I thought that maybe someday that would happen but for the time being, I had to get to terms with this dildo. By now it was quite late, and so I threw on some shorts, leaving my panties on underneath, I slipped out of my bra and took the dildo in a t-shirt to the bathroom to clean off and get the makeup off my face. I chuckled as I ran my soapy hands quickly across the length of it, thinking ‘eight inches long, seven and a half insertable..’
Insertable? Hmm..