Pledging a Prestigious College Fraternity with the Help of a Sexy Crossdresser [MT]

I grew up in a small college city. A prestigious private university, a well-regarded state university, two small liberal arts colleges and a community college made for a very interesting environment.

Following high school I ended up attending that private university. After settling into classes, my friends and I began to attend some of the rush events hosted by fraternities tied to the different schools. The fraternities weren’t located on campus or on a fraternity row of any kind. They were located around town in areas largely populated by off-campus student housing.

It would have been absurd for me to actually pledge a frat. All locals were trained to dislike “frat boys” beginning at an early age. Joining a frat was unthinkable, but their beer was cold and free.

The parties were a lot of fun. Each frat house had its own character – and gang of characters that lived in them. My far the most prestigious frat in town was Delta Tau Omega (DTO) largely due to its beautiful building. The DTO structure was like a palace which had been sculpted out of marble – an edifice which had been requisitioned by a railroad executive in the late 1880s.

The DTO house was located right around the corner from my parent’s house where I lived and while we appreciated that they were good (and quiet) neighbors, as a fraternity they were still marked with the same brush of hatred by all locals. A distinction earned by other frats who frequently hosted loud parties.

One of the last rush parties I attended was held at DTO. I had always wanted to see the inside of that house and it didn’t disappoint. It was well-preserved and well appointed. Unfortunately its members seemed to believe they were simultaneously attending Oxford and Harvard at the same time. The snotty (and sort of laughable) atmosphere was a big turn off as was the tea in place of cold beer. I had an interesting discussion with the frat’s president. Amazing how logical and articulate one can be when they don’t care about the outcome of the conversation and they’re fueled by caffeine rather than alcohol. I took a pretty good bite out of Chad’s ego and it tasted just swell.

The next day I was studying at my folk’s house when the door bell rang. I opened the door and there was Chad. What the hell? Members of DTO were scouring the neighborhood borrowing brooms, rakes shovels, etc. so they could put their huge pledge class to work on the grounds of the DTO house.

Chad couldn’t believe I was a 6th generation local and that I had grown up in DTO’s very neighborhood. In plain terms I would be a “catch” if DTO landed me – I could be a local emissary to the entire neighborhood. Chad asked if I would like to join DTO’s pledge class (a honor to some in itself.) I said I would like about it (yeah, sure!) as I loaned him some gear.
Later that night I told me dad about what had happened. He actually supported the idea of me joining a frat – particularly the upscale DTO. I was a little flabbergasted to be honest, but it made sense as my dad had went away for college and didn’t quite carry the hatred for frat boys resident in most locals.

The following week I returned home from classes to see my father and Chad having a chat on the front lawn after he had returned the tools. What the fuck was going on? Chad reiterated his invitation for me to rush DTO and this time he had the support of my own dad! I finally agreed but not before pointing out that I thought it was a bad fit, that something less than 1 in 10 aspirants actually got into DTO and that I found it to be a rather snobby environment.

I didn’t really get all that enthused with the pledging process. Not really caring if I got in or not and knowing they wanted me in, completely relieved me of the pressures weighing down the other plebs. I was able to slice and dice the entire panel of DTO members that had been chosen to verbally test us about our knowledge of local history. It was a lot of fun making them look like fools.

The hazing wasn’t all that bad. Still, the pledge class has shrunk from over 100 to 19 due to the (largely mental) bullshit we had been subjected to. While the hazing was constrained by that Oxford/Harvard mindset, it certainly ended with an intense bang(ing) that I would have never expected.

It began with a fairly elegant meal at the DTO house. Martinis before dinner, wine with dinner and then followed by huge snifters of brandy – a lot of drinking which was out of the character for a DTO event. I for one felt very relaxed to say the least.

We were told that our final hurdle would take place at the Lambda Psi Rho (LPR) house across town. With that we piled into some vehicles and made our way to LPR. While it was no DTO castle, LPR was also a nice large (in its former life it was a Franciscan friary), immaculately kept Spanish revival house with a putting green for a front lawn and what seemed to be beautiful flowers everywhere.

We were met by LPR brothers at the door and guided to a room where we were directed to strip to our birthday suits and to enjoy a beer or a shot or two from the ice chest. They came and got us about a half hour later and herded us upstairs to a huge, dimly lit parlor room. The evening’s alcohol had done its duty and I had long forgotten that I and my other pledge brothers were nude.

They lined us up – all 19 and I minute or two later they marched in 19 women, each stereotypically dressed like high class call girls. The push-up bras, bustiers, garter belts, hosiery and sexy heels were all a sight to behold. Some of the women looked like moviestars.

We were paired off into couples, just standing there in the dimness, when I heard the first screams and curses, followed by 5 of my brothers bolting for the door. What the fuck!?! The “girls” had removed their panties to reveal they were actually LPR members who had crossdressed for the evening. That explained LPR’s reputation (known only to observant locals) as the local “fag frat.”

I looked over at my “date.” Perhaps it was the alcohol, but (s)he looked absolutely sexy. Were it not for that small dick between her legs, she would be dateable. Actually she would probably be out of my league.

Then the asshole-in-charge gave those of us remaining our second challenge. The LPR gurls were to stroke the DTO boys to erection in unison, with everyone watching. I could see a few more head towards the exit. That left a total of 12 couples.

In a rare flash of mental toughness I decided to endure. I looked at Abigail as she approached me. I could see that she was also uneasy and that it was some sort of test for her as well.

Abigail really was pleasing to look at. Sexy as hell! With her 4” stiletto heels she was the same height at me – 6’3”. She was quite slim but toned, totally smooth, with a truly world-class bottom and tiny, pert boobies. Her long brown hair was real – she had gotten a hairdo that day for the event, and her black bustier and garter belt looked as if they had been custom tailored to her body.

Abigail made it very easy for me to succeed at this challenge. She routinely crossdressed unlike most of her sisters so she knew what she was doing. She was also considerably hotter than any of her sisters – at least of those who remained. She discreetly spit in her hand just before touching me for the first time. I was already a tiny bit aroused – even under those circumstances so it made things very natural.

I was amazed by her hand – very soft, with long tapered, feminine fingers. Her long fingernails looked intensely sexy and deliciously slutty in Ferrari red polish. It took a bit of effort but I was fully erect in no time. Abigail was pleased and smiled when the dickhead-in-charge judged that I had satisfactorily completed the challenge.

He then said, that based on the looks of things, perhaps I had enjoyed it too much? With that I went ballistic. “Listen asshole, you pair me with Abbey who looks like a cross between a tall Jennifer Aniston and a tall Kaley Cuoco, you tell her to stroke my cock and you don’t think I’m going to get hard? What the fuck did you think was going to happen? Are you come kind of fucking idiot? Fuck you and the horse you rode in on!”

I looked over at Abigail and she had a huge smile on her face. I actually winked in response – I’m never that cool, but I was that night. That release of tension would prove to be a key in that evening’s outcome.

Back to reality, the murmurings from those around us ranged from the desperate (some guys just couldn’t get hard), to the quiet (both defeated and victorious couples) to the loudly triumphant. All in all, 9 couples remained.

Our final challenge was the kinkiest of the evening. Each LPR gurl would escort their DTO dates to their bedrooms where they were required to make their partners cum. Hand jobs, oral, foot-jobs, intercourse, whatever was approved but absolutely no masturbating was allowed – we were not to touch our own cocks! We would be periodically monitored to make sure we were playing by the rules and that the DTO’s had cum.

Abigail led me back to her room. We sat on her bed and talked and she confided that to join LPR she had to make me cum. Talked turned to flirting when the door opened for our first “check-up.”

The dickhead-in-charge pointed out the obvious – that talking wasn’t going to complete the challenge. After telling him to take up his own challenge by fucking himself, he left with his tail between his legs.

Our flirting resumed as Abigail reached over to stroke me. I responded by growing in her hand and by reaching over to touch her – the first time I had ever touched a cock other than my own. I was rather amazed and turned on that she was too was also becoming erect.

Very carefully, after summoning the guts, I asked if she would consider oral, or did she want to stay with a hand job? After obviously gathering her own courage she quietly asked “would you like to fuck?” while cringing a little in preparation for rejection.

I smiled and said that would be ho! She really lit-up and went to her dresser to get a condom. Very lovingly she cupped my balls as she rolled the rubber onto my rock hard cock. Handing me a second condom she said “I don’t want to create a huge mess.” I finally got the hint and rolled it over her cockette.

She wanted to get nude and I nodded. She looked even hotter in the nude – like a supermodel sans all body hair plus a dick. I could see her small cock standing straight up against her flat stomach. While still standing she began to discreetly lube her love sphincter. I took the bottle from her hands and began to help her. She and I were both shaking at this point when the fucking hall monitor opened the door once more. After roaring at him again, he left, but not before seeing two hardons and me generously lubing her bottom.

I laid back on Abigail’s bed and asked what position she wanted to try? She smiled and straddled my body as she replied “cowgirl.” Even though I was steel-hard at that point, it took some concerted effort to get my cockhead inside of her. It finally disappeared inside of her and ever so slowly she lowered herself onto my cock until I was balls-deep inside of her. I couldn’t believe just how TIGHT she was!

Our bodies softly swayed together. I confessed this was my first time with someone of the same sex. She nodded and then apologized – she had not had much experience at anal and never with a guy my size. I grinned and nodded back.

I playfully pinched her nipples and her bottom instantly gripped my dick with even greater tightness. Placing my hand on her back I pulled her down to me so that I could suckle on her nipples. Her moans of ecstasy sounded not only like pleasure, but a release of a great deal of frustration and tension.

It was a great pleasure just laying there. Our two bodies static – my cock just soaking and swelling ever bigger inside of her, as I continued to suck on her nipples. Her asshole was clamping down on my cock with ever more ferocity when she said “let’s really fuck in the missionary.”

That sounded extremely sexy to me so ever so carefully we rolled over in her double bed. She repositioned her legs so they were draped over my legs and we began to pump like a well oiled machine.

We began to kiss on the lips – my first with someone of my own sex. That beautiful sound of my balls slapping against her ass was like erotic music to my ears. Abigail was a very aggressive French kisser – an absolute pleasure.

She began to stroke her own cock as I continued to hammer away at her asshole. We moaned and grunted in concert as our lovemaking hit top gear. In between kisses she said she wanted us to time things so that we would cum together. I grunted my agreement.

I was sucking on her tongue and driving my cock deep up her ass when she managed to say she was close. I replied “me too” and in another 2-3 minutes of hard thrusting our bodies absolutely exploded with lust. I yelled loud enough to be heard back at the DTO house across town. My entire body jerked with every spurt of hot white cream.

Abigail was screaming as she began to cum. Our cries of passion where absolutely over the top with lust. It wasn’t until a few moments later when we finally noticed several people peering at us from the foot of our bed. They erupted into applause once we noticed them. Once more I told them to get the fuck out, and they did.

We just held one another for a few moments. We has just shared a truly hardcore experience of passion that left us breathing hard and our hearts pounding.

Abigail then very carefully removed my condom using both her fingers and lips. She took my cock deep into her mouth and sucked every bit of cum from my dick. She then did one of the sexist things I had ever seen in my life – she drank the remaining cum from my condom. She then began to remove her own condom. I stopped her and returned the favor – another first for me.

I was heartily accepted into DTO (and Abigail into the LPR) but I was never really enthusiastic about being a member – although it did have its advantages. They didn’t dare kick me out – after all, I wasn’t just a local, after that show I was a legendary local who went all-out for challenges.

Abbey and I met for a great many more discreet, “midnight dates” in her tiny, safe bedroom on the top floor. She would dress for me and we always enjoyed one another as the ultimate pair of very special friends with benefits…

Source: reddit.com/r/gonewildstories/comments/7r9t8b/pledging_a_prestigious_college_fraternity_with