Why I hate Colonial Williamsburg

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Tricked into a stockade, guy is stripped, teased and pegged.
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Gaius8666
Gaius8666
790 Followers

My name is Ted, and like many people I look back very fondly on my college days. Those Halcyon days were some of the wildest times of my life and I certainly wish I had appreciated it and enjoyed them more when I was there. Now that I am older, I still think back in amazement at the crazy things I did, and would give anything to relive those times again, if only for a weekend. Back then it was all hot coeds and endless keg parties, now it is mortgage payments and insurance, so things are sadly very, very different, and NOT for the better. Despite having many fond memories of college, the sight of any shot of Colonial Williamsburg still gives me heartburn now twenty years later.

I went to William & Mary back in the 90s and it was beyond fantastic. So many hot women, so many drunken nights, it now seems like a never ending blast. Mostly my memories of those times are just a haze of non-stop partying and endless pussy, although it was no typical "party" school. Ironically the best part of attending when I was there was the high percentage of very attractive young women that were students.

The college, for those who are not familiar with the school, has the town of colonial Williamsburg essentially cutting right in the middle of campus. Founded in 1699 it is one of the oldest institutions of higher learning in the United States and everyone is pretty much in agreement that it is the most beautiful college in the country.

Being in the middle of the restored city of Williamsburg, Students and Tourists mill about constantly thrown together in a perpetual mix. It is not odd at all to see coed hotties cutting across The Duke of Gloucester street as they try to make their class on time running straight into crowds of dazed middle aged couples fecklessly meandering through the streets with their dull eyed fat children all wearing tri-corner hats. It never is exactly clear where William and Mary ends and Colonial Williamsburg begins.

One of the more popular sites in the touristy part of the old Colonial Town is the main square with its obligatory stockade. Every family fresh off the farm from Iowa seems compelled to have their picture taken with someone (usually the Dad) bent over with his head and hands in the stocks pretending to be a Colonial Prisoner. Although just for show, these are real stocks and if locked they would be impossible to escape. For people who actually LIVE in Williamsburg, this charming scene has long ago grown tiresome, and the plague of tourists infesting everything are both craved for the money they bring in, and mocked for their garish goofball ways. Too many "I'm with Stupid" T-shirts, flip flops, and shockingly inappropriate shorts having made the actual residents quite jaded about outsiders.

I hate to admit it now, but I was a total pig back when I was a student. Not to brag, but I was fairly attractive back in those days, practically LIVING at the gym, and given that William and Mary had a ratio of 2 women for every man made the pickings shockingly easy. That coupled with the fairly high ratio of complete geeks that represented most of the male students, any guy with just average looks and a moderately sized functioning penis would usually do quite well in this target rich environment. I had my pick of an endless stream of hotties as the girls at that college found the inventory of hot men relatively small, so the odds were in my favor.

Rarely did a weekend go by that I did not have some new young naïve freshman girl's panties laying on my floor as her delicious snatch sat on my face. It was absolute heaven and foolishly I thought those days would never end so I did not savor them for the rare event they were. Even so, I did thoroughly enjoy myself and left a long string of broken hearts all the way down the cobblestone roads of Old Towne. Never thinking about the consequences of my swinish attitude, I never dreamed that my ways would come back to bite me, but as they say Karma can be a bitch sometimes.

I can still remember the event today, nearly twenty years later, as it was the most humiliating day of my life. I was walking back to campus one warm EXTREMELY late spring evening and was kind of drunk as usual. The streets were completely bare as it was truly the middle of the night, and with exams coming, everyone was back in the dorms studying or sleeping. Staggering back towards Dawson Hall I was shocked when two girls came up out of the dark and approached me. They were both knockouts so I certainly did not mind them to me chatting ME up, but I did find it odd that they seemingly came completely out of nowhere.

Now, as I said, I was pretty attractive back in those days, but I certainly was not THAT attractive, so in hindsight I should have known something was off. Here it was the middle of the night and two girls approach a drunken college guy to start flirting? These things just do NOT happen and I should have immediately been alerted to something nefarious. Beer, testosterone and my then relentless and insatiable male ego can definitely cloud my judgment and it definitely clouded it that night.

They were extremely flirty, quite over the top, and made sure to make lots of physical contact so I knew they were interested. As both were scorchingly hot I was instantly attracted and quite intrigued. Saying they were going to go share a bottle of wine on the commons and were looking for a little bit of male companionship they asked if I wanted to join them.

I was gobsmacked at my seemingly insane good fortune. For years I, like EVERY straight man, had dreamed of the ultimate holy grail, the mythical threesome. Now right before my eyes it appeared that the circumstances might be presenting themselves for just such a fantastic event to actually occur in reality instead of just in my hormonally supercharged imagination! Who knows, maybe there would be TWO pairs of panties hitting my floor tonight if I played my cards right, I conceitedly thought, so of course I joined them.

It was extremely late, around 2 am, but still light enough to have a conversation as it was a full moon that night. One of the girls seductively stroked my bare leg with her equally bare foot so I knew enough about women to know she was attracted to me, and I grinned to myself. As we all drank and talked I was getting not only drunk but quite horny after about 20 minutes of light flirty banter as we finished off their wine. When the girls suggested that we play truth or dare, I couldn't believe my luck, but suggested that we take it inside (maybe my Dorm room?). This seemed to annoy them and they insisted that since the evening was so nice it was much better to stay where they were. Not wanting to blow it, I acquiesced as I continued to secretly plot a way to get them back to my room and thus into my bed.

Sitting out in the wide open lawn of the commons, the night was as beautiful as the circumstances were surreal. Bathed in the soft silvery glow of the full moon, both girls looked incredible. Dressed in shorts and t-shirts, their lovely female charms definitely showed through their casual wear and I was drooling. Both were stacked and showing just enough bare skin to keep my idle high. As they kept brushing against my arm, or touching my hair, my knowledge of women told me what I most wanted to hear, and what it told me was that they were BOTH interested in taking this evening in a sexual direction. The first rounds of our game were mostly truths, but their questions to me kept getting bolder and raunchier When Kathy (one of the girls) asked me how much meat I was packing, while simultaneously checking my crotch out through my shorts with her toes, I nearly creamed right there.

"Ted, don't you love getting kinky and playing outside?" Kathy giggled as my arousal was now quite apparent.

When it was my turn I asked the girls whether they wanted truth or dare, and to my amazement and delight, they said dare. Getting bold myself, I dared them to flash their tits, and for a second I regretted blurting out such an obvious request. My heart stood still as I waited for their reaction, fear gripping my balls as I hoped I had not blown such a golden opportunity.

To my surprise and great delight, they looked at each other and winked, not hesitating to comply and instead of flashing me, they took their shirts off and revealed their full naked perfect breasts underneath. Now with four full round babies staring at my hungry eyes, I was extremely hard.

Even though I was drunk, I nervously looked around the deserted square to make sure we were alone as we were now out in public and with two half naked girls and I certainly did not want some Campus Rent-a-Cop coming by and fucking it up. After they had taken their tops off they stood over me sitting on the ground and waved them in my face before leaning over and grabbing my face. As each girl tongued my throat in a toe curling passionate kiss, she giggled saying that that was a freebie. The effect on my libido was instant and now I was going crazy, my whole body burning to get them back into my bed ASAFP!!

When it was their turn and they asked Truth or Dare, I boldly said dare. The hypnotic effect of their beautiful tits swaying in the night air, and the effects of quite a bit of wine I had scarfed down made me feel pretty invincible at that point. Giggling, they pointed across the commons towards the main square and dared me to get into the stocks so they could take my picture.

I was at first surprised by this request as it seemed so cheesy, but given that they had were still topless, this seemed like a very harmless dare and much less of a commitment than I had demanded of them. Still, posing in the stocks was something tourists do, not students, and I wondered why they were so insistent on THAT as my dare. I certainly did not argue though as I remembered that the first rule of getting pussy is, Do NOT ARGUE WITH THE PUSSY, OBEY THE PUSSY, so I gladly stepped up on the platform, laced my arms and head through the hole and prepared for my picture to be taken.

I guess in hindsight it was because I was drunk, or horny, or drunk AND horny, but I honestly did not see the Kathy take out the padlock from her purse. Once I was in the stocks and smiling like a big doofus I heard the ominous CLICK and found I was locked in and quite helpless.

For the first few minutes, I pretended to struggle as the girls took LOTS of pictures. I figured this was all a big joke and definitely wanted to humor them as I had OTHER plans for how this evening would end. I never suspected anything was up until the Melinda (the other beauty) asked me if I knew who they were. I turned on the charm and said they were some smoking hot girls I had just met that night, but honestly did not know who they were as I did not think we had ever met. "Well, I am sure you will remember us after tonight. We are Donna's roommates."

Hearing this my blood ran cold and now I started to struggle, but this time I was not faking, my desperate thrashing was for real. Donna had been my "girlfriend" for six months at least up until a few months earlier. I am not proud to say it, but I treated her pretty badly even more piggish than usual, so hearing her name was chilling. She had fallen pretty hard for me the prior summer, and was gorgeous, kind and hot as a August blacktop in Texas.

For my part, I cheated on her constantly and was a complete dog, actually seducing her little sister who came up for freshmen orientation. That obviously caused a MAJOR rift and we had a pretty bad breakup. Things were said that should never have been said and I knew she had been pretty pissed when we last saw each other as we did NOT part on good terms.

Thrashing wildly in the surprisingly effective stocks, I now demanded to be let go. Having put their tops back on, the girls just stood in front of me with their arms crossed over their recently bare chests and chuckled. When I saw them start rooting around in their purses my mind conjured up all sorts of dark things that might happen to me now and my concern grew into a panic.

When I saw the scissors in Kathy's hand I got VERY scared. Not knowing what they were going to do I was certainly hoping that the night was not going to end in some kind of violence. Even though RATIONALLY I was pretty sure I knew they wouldn't actually hurt me, my balls shivered as the idea of being castrated by two crazy girls flashed through my mind as it did not seem as farfetched as you might think. Thinking back on the look on Donna's face when she burst into my dorm room and found me on top of her sister, it DEFINITELY was not out of the question.

Seeing my increasingly panicked reaction, Kathy, laughed as she held the scissors up to my face. I had dramatically sobered up now as I glared at the shiny metal in the silvery moonlight and I started to blubber out apologies.

"Look girls, I, well, Look, don't do anything crazy now. Just let me go and I will forget the whole thing. Listen, you won't get away with this so." With my whole body shivering, I was really scared and thought for a second I would piss myself.

Covering my mouth with her hand, she ran the blade down my chest and I flinched as I felt the sharp point poke into my crotch.

"Hey Melinda, this PIG thinks we are going to chop his dick off."

"Not a bad idea though, you know?" Melinda chuckled, enjoying watching my growing fear and shaking body. "We could apply it to our community service requirement for graduation! Sort of our contribution to the betterment of womankind."

Grinning wildly, I watched Kathy's face carefully as she now circled my completely shrunken denim covered cock with the scissors. Being in the stocks with my head frozen in place, I was forced to look only forward, but I could still feel the steel against my body so I was EXTREMELY nervous.

"Yea, no doubt his junk would not be missed. BUT, if we cut it off it would not get to make its world premiere."

Feeling her remove the blade from my crotch I exhaled loudly into her hand as she took it away from my mouth. I still did not know what they intended, but I was convinced my family jewels were at least safe.

Now more calm, I picked up on what she HAD said and got worried again, the words "make its world premiere" ringing in my ears. When they started cutting my shirt away, I really struggled as it was now clear what they were going to do. As I felt the remains of my shirt lifted away, and then completely shredded I realized that once they took an item off of me, they were going to make sure to destroy it totally so I could not put it back on. As my shoes and socks were pulled off I prayed they would stop and not really leave me out here totally naked. Still I said nothing, hoping and praying that they would stop soon and realizing that begging would probably not help. Already envisioning myself bent over in the stockade naked I mentally prepared myself for quite a humiliating morning, but I still hoped to at least be able to keep my shorts.

Feeling my belt pulled off I began to struggle again as they showed no signs of stopping or even slowing down my march towards total nudity. Finally, I could no longer stay silent, and thought maybe I could charm them into some mercy.

"OK girls, this is funny but the jokes over! Look, any minute I am sure one of the campus security guards is going to come by, and if you let me go now, I promise not to push this any further."

Laughing, they continued to snip away, now holding the hem off my pants out so they could cut up the outside of my jeans. Hearing my attempts at charm, Melinda laughed and responded.

"You know it's funny you mention that. IRONICALLY enough, or possibly NOT that ironic, Donna has a date with the guard that was supposed to be on patrol tonight. Now, what do you bet that your sexy ex is going to keep him quite occupied while we go about our business and make sure we have plenty of time to do what we need to do uninterrupted."

Now my face turned pale as I realized that they had this planned this out very well. My face turning red, both in anger and humiliation, I thrashed violently yet futilely in the stocks. As I saw the shreds of my jeans tossed onto the pile of my ruined clothes I knew the moment of truth had come.

Now left only in my briefs the girls paused and stood in front of me glowering, enjoying the sight of my helpless struggles and admiring the odd performance art piece they were obviously creating. Seeing them standing before me, and feeling the warm spring night air blowing over my bare legs and chest, I knew I must look like quite the sight. Reduced to just my briefs, a tiny thin white piece of fabric was all that stood between me and total nudity. Seeing them temporarily stop, I took the opportunity to beg like I never had begged for anything before in my life, thinking that perhaps I had a chance to spare myself COMPLETE humiliation.

"Look, please, I am a pig, A LOWLIFE PIG I admit it. Donna was too good for me and I treated her like shit and for that I am really sorry, really. Please, you have made your point. Don't leave me out here naked! I have seen the light!! I swear I HAVE SEEN THE LIGHT!!"

Watching me beg the girls were unmoved and with a knowing glance, they both winked at one another.

"Well, perhaps you have Ted, perhaps you have" Kathy smiled as she nodded and looked me up and down. Walking up close to my face I could smell her perfume and look down her shirt at her glorious cleavage and the tops of those globes that just moments before were on display to me. Feeling my bare chest with her fingers I flinched.

"You know Melinda; he is kind of cute." Reaching back behind me, I felt her fingers stroke my quivering ass through the thin fabric of my remaining shorts. "And his ass is JUST as tight and fine as Donna always used to say it was."

Squatting on her knees, I could no longer see her, but I could feel her breath hit my crotch as obviously she was eye to eye with my dick. "And soon we will learn whether all of her tales of his dick were true after all."

Kathy strolled over and joined in the inspection, running her hand down my hunched over back while playing with the twitching deltoids. "Yeah, she said Ted worked out and now we know it's true." Coming around to face me she stared deeply into my eyes.

"So, if we let you go are you going to be a new man? Not fuck around on your beautiful girlfriend's anymore? Go apologize to Donna on your knees?"

My heart soared as I saw daylight in this long night of gloom by her words. Perhaps this whole thing had just been some elaborate scheme to scare me, and if that was the plan, it had definitely worked! Now I would truly say anything to get loose and avoid being publicly humiliated and I began to beg once again.

"ABSOLUTELY! I swear, on my mother's life I swear! I am a new man; I have gotten the point. In fact, I was just on my way over to Donna's house to apologize tonight, as a fine woman like that deserves much better than some pig like me!"

Laughing both Melinda and Kathy stood up and patted my cheek. "Oh Ted, you are such a charmer. A lying little fuck but quite a charmer! Do we have to tell you how much of an obvious lie that is? If you were going over to Donna's to apologize how did you end up in this ridiculous predicament in the first place? I tell you how, by following your DICK after what you thought was going to be fresh PUSSY that's how! Well, save your charm fucker. After tomorrow, you are going to need every ounce of it."

As I began to open my mouth to beg again, I felt Kathy slip the cold steel between the fabric of my briefs and cut. SNIP SNIP was all it took and the remains of my briefs were pulled away, leaving me completely stark naked and quite helpless.

Angry, I began thrashing again as my nudity was uncovered. They said nothing but just stood and giggled as they watched me exhaust myself in the prison of hard wood and iron for five minutes, my exposed dick and balls jangling helplessly in the night air.

Gaius8666
Gaius8666
790 Followers
12