Renfaire Virgin

Seated at the small table in my equally small apartment, I sat down with a cup of coffee and opened my email to see what was happening - or more likely, what wasn't happening. As I sniffed the French Roast, I was surprised and pleased to see an email from "Dungeon Master." 

While in college I was, at times, included in a group who met on Saturday nights to play Dungeons and Dragons at the Rathskeller over pitchers of cheap beer. We all had our fictional roles. I was the Wanderer who was good at exploring but weak at fighting.  

The whole thing was orchestrated by a really hot girl named Christine and just known as Dungeon Master on those Saturday nights. I hadn't kept up with the D and D people in the three years since graduating.   My social life was mostly watching movies by myself in my cramped apartment. I clicked to open the email.

Hail good friends of the days of yore from D&D! I send forth a merry call for assistance in a time of need. A stout and reliable soul is needed to pour and serve grog this weekend at the Renfaire. Camp for free in our fine tents with the folk of the Faire and know that an elegant costume and garb will be provided. Come lend a needed hand and join the merriment. Huzzah!

I nibbled a strawberry Pop-Tart and I thought: Why not?' I had nothing else going on and seeing curvy Christine - and the other hot D&D  girls might possibly lead to something I'd never even been to a Renfaire - but there's a first time for everything, right?  

I emailed back immediately, and before my mug was drained, she had responded giving me the details of when and where to join on Friday night.

***

Christine, a soft and full bodied woman with a prominent bust and jet black hair to her waist, sat across the campfire from me. Her D sized breasts pushed up and out like they were trying to escape from her leather bustier, a part of her Renfaire outfit. It was impossible not to look at her bulging cleavage as the four of us sat around the campfire Friday night.

Angela and Sybil had been part of the D&D  group too. Christine, Sybil and Mary, along with Priscilla Lambert had been really close, almost a clique. Priscilla wasn't here this weekend because of a family thing.  

I had lost my virginity to Priscilla my senior year. It was a one-time -thing, and if I'm telling the truth, the only time I'd actually done it, since she couldn't make it this weekend, it was just Christine, Sybil, an Mary and me.   We would be serving Festival Ale at what I learned was "The Goode Wench Tavern." Christine managed the Tavern for the local Renfaire and the other girls assisted.

Like Christine, Sybil and Mary were in period dress of sorts as well. Sybil, lithe and a little taller than me, wore a blouse with puffy sleeves and was low cut so her cleavage, though smaller than Christine's, was quite inviting.  

Sybil wore a flowing emerald green peasant type skirt that set off her red hair brilliantly. Where Christine was the leader of the group, Sybil was her reliable assistant, always agreeing with her.  

Mary, a natural blond, wore a ruffled crop top that showed off her thin waist. She didn't seem concerned at all by the skirt that just barely covered her firm ass that allowed glimpses of her red panties while standing or sitting on a log around the fire. Mary was the one who usually wanted to break the rules.

Sybil, seated on a log to my left, noticedl my wandering eyes. "Sir Bob, I see you find the countenance of Christine desirable." 

She moved her hand up and down in front of her crotch suggesting an erect penis. The three women all laughed at that.

I played along with their laughter, "I so enjoy the sights of the Faire," trying to go with the goofy way they spoke. I tucked my pelvis in hoping my hard-on wouldn't be so obvious.

"Right you are, Sir Robert, the sights of the Faire draw the crowds. We must be prepared to assist them with spending their coin. And so those of us serving the ale, dress as the wenches, they wish us to be. Good of you to make yourself available when Priscilla couldn't make it." Sybil said."

"''Tis a shame Priscilla couldn't be here, too. Please convey to her my fondest greeting." I felt like I was picking up some of the Faire-speak.

Mary turned to me, "Didn't you and Priscilla have a thing once, Bob?"

"Well, yeah, we did. Truth be told, that's who I lost my virginity to. But probably most proper not to speak of such things now, as I'm a gentleman." I didn't really want to be talking about this.

Christine leaned forward, over the low campfire flames, "So then, you're not a virgin? Because of that night with Priscilla?"

"No, of course I'm not a virgin. I'm 25 years old!   --  But anyway, how shall I dress for the Tavern tomorrow? A leather jerkin and linen trousers?" I wanted to move on from the Priscilla discussion.

Now they all sniggered loudly.

"Your dress for the Faire is in our tent. Sybil, would you get it so it can be tried on? The fit should be good with only a little adjustment." 

The tent was one of those big ones made of canvas where you can stand up. I'd seen four cots and a storage chest in there earlier, I guessed that is where my costume waited.

I should have known there was a problem when Sybil and Mary actually laughed out loud.

"A dress! I can't wear that! I'm a boy!" I yelled when I saw what Mary was holding.  

A fitted bodice with wide long sleeves, boat type collar with lace trim, about calf length. A champagne white with a yellow ribbon sewn around the hem and around the bodice completed the look. Admittedly cute in a historic way. Coquettish.

"So here's the thing, Bobbie," She emphasized saying my name as 'Bobbie'" rather than 'Bob'- "It's called the Goode Wench's Tavern, and the ale is served by a wench. So -- that's what we need you to be. Wear the dress, curtsy and be a wench. You can do it." Her voice was firm, no more of the Renfaire lingo, just a statement of command.

"No way, that would be too embarrassing. Really." I said.

They all laughed together and Christine said in a low steady voice,"More embarrassing than being a 25 year old virgin? Because Priscilla told the three of us what really happened. You shot your cum on her thigh. Never made it inside. Only the four of us know. Wouldn't you like to keepit that way?" 

Her eyes bored into mine and I looked away down to her boobs popping out of her dress.

This is what I feared ever since... But I thought I had gotten away with it -  Priscilla had never said a word.  

"Ok, ok, I'll do it. Be cool about it and don't tell anyone. But I'm wearing my shorts underneath." 

At least I'd have that for my pride.

They all guffawed.  

"Bobbie, you'll be wearing a bra. That's how you get tits. And so you might as well wear the  panties too, Bobbie." Sybil added, as she uncrossed her long legs as she spoke.

We all slept in the big canvas tent on individual cots that night. I could hear Mary and Sybil giggling in the dark until Christine told them to go to sleep. I was thrilled to be so close to them, but also nervous about the next day.

In the morning, I was given granny style white satin panties and a white stretchy bra. The bra had a thin edge lace along the B sized cups.  

I tried to refuse but Christine was unmoved. Mary stared right into my eyes and Sybil snickered. I had to pull the panties up in front of them!

Mary showed me how to put on thea bra. She had me wrap it from back to front so I could connect the hooks, wiggle it around my chest so the cups were in front, and then slip my arms through the straps. Pretty easy, actually. Sybil stuffed the cups with tissue paper, then Mary stuffed even more in.

Maybe I should have fought back more, but I actually loved the attention they were giving me.  

Mary stepped back to look at me and said, "Bobbie, this can't be too bad, can it? Your dick is saying it likes wearing panties and a bra?"

Sure enough, my cock was growing hard in the slippery white panties.  

They all laughed at me, again. I felt a tingle down there when they laughed at me, wearing panties and a bra for the first time in my life.

The elegant dress flowed from my shoulder to my waist to just above my ankles. I couldn't help but twirl and watch the dress flow around me. It was a dress for a princess and it was a dress for me.  

Christine handed me a wig of shoulder length brunette hair I put it on and curtseyed.  

The girls gave me a small applause. I had never known that feeling pretty could make a person feel so happy.

At first I was shy and embarrassed carrying mugs of Budweiser (we just called it Festival Ale)  to thirsty faire goers, but no one seemed to notice I wasn't really a girl. I think I did a pretty good job acting like a medieval wench because I got my butt patted several times. One guy with a long beard tried to push his face into my fake tits. I instinctively twisted to the side at the last minute, making his friends laugh at him, and keeping my secret safe.

That night, after the visitors had left, it was just the people working the Faire. We sat around our small campfire. I stayed in my dress, the panties and bra. The girls still had on their revealing costumes too. The Tavern had been busy and profitable, we were tired but in good spirits.

Christine complimented me, "Bobbie, great job today, you kept the beer moving and the customers happy."

I was pleased to hear that and smiled.

Mary, always the one to make a little trouble, added,"I think she deserves a reward. Wouldn't it be something if she was no longer a virgin? Sybil and I think she deserves it."

I caught the use of "she" rather than "he", but assumed that was just Mary teasing me for still wearing my dress --. Whatever. But actually losing my virginity? Hell yes!

Sybil added,"Mary and I have something for Bobbie in the tent."

Christine, being the leader, asked "Bobbie, are you sure you want this? You don't have to."

In answer, I stood up and opened the tent flap. All I could think about was actual sex, and with three hot girls! They all followed. Christine tied the tent flaps closed.

Mary immediately put  her arms around my waist from behind and kissed my neck. Sybil came around to my front and pushed her groin into mine. My cock, already hard, twitched up and down.

Christine sat down on a cot and back in her Renfaire style, said "Unzip our dear lady's dress, and let the jolly times arise!"

Mary pulled the zipper down from the back of my neck to my waist and Sybil pulled the shoulders off me. I pulled my arms out of the sleeves and Mary yanked the dress down. I gave an involuntary shimmy to help it along. They left the white bra in place and Mary reached around from behind and rubbed my cock through the panties. I was leaking and there was a dark spot from the wetness.  

Sybil stepped back and removed her costume. She was completely naked. Her long red hair fell in waves to her bare shoulders. I reached out and put my hands on her breasts. They were soft and magical. I moved to feel her russet colored nipples. They enlarged and hardened under my fingers.

Christine stood up and proclaimed "And merriment will be had by all!" 

She took off her bustier letting her breasts fall onto her upper abdomen. They jiggled like large bowls of jello.

Mary was next and slipped out of her clothes. Her breasts were smaller than the other girls, but her nipples seemed extra long and pointed slightly upward towards the blond hair framing her face.

I started to undo my bra, still stuffed with tissue paper but Sybil told me to stop., "No Bobbie, we like you dressed as a girl."

Mary and Christine laid down on a cot and I saw Mary put her lips on Christine's large breasts. Soon they had their hands in each other's pubic hair.

Sybil lay down on her back on another cot and spread her thighs. "We're going to fuck you," she said, "but first you're going to make my pussy cum with your mouth."

I was immediately on my knees and nuzzled her red pussy hair, then gently circled her labia with my tongue.  

She moaned.  

My face was wet with her juices.  

I could hear Mary and Christine breathing hard and making grunting sounds. Sybil pushed my head down and threw my wig to the side, she just said "Tongue inside."

As I pushed my tongue in as far it could go, she reached down to her clitoris with one hand and rubbed it back and forth. Her pelvis rocked back and forth and I explored every bit of her vagina with my tongue.  

Warm salty juices flowed around my cheeks and chin. I looked up and her hand was pulling on a nipple. Her head tilted back and I think her eyes were closed.

Mary and Christine had moved into the Yin-yang position for a 69 and porpoised up and down in unison. Christine was on top and Mary gently patted Christine's full ass in rhythm with their undulations.

I felt Sybil's body shake and she let out a string of "Oh, oh, that's it, Oh, oh." as a wave of pussy fluid filled my mouth.

I think all three of the girls came within a minute of each other with Mary yelling "Yes, yes, Oh my god, yes."

Christine grunted loudly multiple times.

After a few minutes Sybil pushed my head away from her legs and said "And now Bobbie, it's your turn."

Christine stood up and said "Assume the position to welcome me, Miss Bobbie, and you shall be a virgin nevermore." 

I didn't think I needed to be held to put my dick in her, but whatever she wanted was fine with me. Obviously I hadn't understood yet what was happening.

Mary and Sybil, still slick with sweat, told me to stand up and then bend at my waist. Mary held my shoulders down and Sybil held my hands behind me. She gave my bra strap a tiny snap.  

The next thing I felt was a smack on my ass. A hard smack but it was like electricity through my aching dick. Christine was behind me taking something out of the trunk, then she pulled my white panties down below the back of my butt,., the front of the fabric was stuck on my erect penis.  

"Ok, Bobbie. I'm going to take your virginity. You won't be a virgin girl anymore." Christine said evenly and back to normal speaking.

I felt the coolness of gel being squirted on my exposed butt crack and then pressure in my anus and I moaned a little.  

"This is your first time, so it's going to be a little tight. Just relax and push back against me." 

In a flash I understood what was going on. I was being butt fucked with a strap on; pegged. I also knew I wanted her in me. Never before having thought about being pegged, I knew instinctively that I wanted this badly. I moved my ass towards her and she pushed her strap-on cock inside me.  

Oh my god, it felt so satisfying in what seemed like my very center of being. So different than just jerking off my cock, so much more meaningful.  

"Are you ok, Bobbie?" She asked.

"More, please. Deeper." Was all I could utter.

Christine moved back and forth pushing into me and I just moaned and mumbled, "Yes. Please. Yes."

I was hard and dripping. I  had never felt anything so amazing. It's like I'd had a void --, one I hadn't known about --  but now that I did know, I was desperate for it to be filled.  

My cock stretched the thin satin of the panties and I wanted to come so badly, but it was just out of reach, like Tantalus reaching for an apple he'd never touch.

After the best ten minutes of my life Sybil said "My turn."

Christine was breathing hard from the work of fucking me and laid back down on a cot after removing the strap-on.  

Sybil resumed my pleasure and found a new rhythm, adding a grinding motion when she was fully in me. I needed to cum and reached down with my right hand, but Mary was there and she pulled it back.  

"No, Bobbie, not until we've all had a go."

After another ten minutes Sybil was covered in a thin sheen of sweat and laid  down on her cot.  

Now Mary had her way with me and pumped faster than the others had.

Finally, Christine came to my rescue.   She stood back up and put her hand on my stretched soaking panties resting on the head of my dick. Her touch was both delicate and firm. That was all I needed, I exploded, shooting my cum into the wet white panties.  

Mary pulled out of my ass and I collapsed on a cot, more satisfied than I'd been in my whole life. Not only had I been to my first Renfaire, but in one way at least, I was no longer a virgin. And I discovered crossdressing -they even let me keep the white bra and panties!

***

I started hanging out with my old D&D friends again, giving me a much needed boost to my post graduation social life.    

A few months later I hooked up with Priscilla. She had heard about Bobbie/me losing our virginity and she was curious.   Curious enough to want to give Bobbie a long ride. And then - I think out of kindness and generosity -- she let Bob/me finally lose our virginity in the usual fashion.  

Another great thing about the Renfaire weekend was I learned the pleasure of crossdressing. Its not like the acute, focal ecstasy of having my dick fucked or rubbed, or like the profound inner satisfaction of being pegged, but more of a feeling of peacefulness all day long. Sybil and Mary even took me on a shopping trip to Victoria's Secret.