Skirting The Issue

Brenda and I had been seeing each other occasionally that summer. She was a stunner in her mid twenties with long dirty blonde hair, nice medium sized tits and great legs. There was nothing exclusive about the relationship but it was frequent enough that I'd say we were an item of sorts. I'd met her at a topless club I used to frequent. It was actually kinda funny - I went there to touch base with my accountant at lunchtime once a week or so and ended up running into all sorts of business acquaintances there.

One day I gave Brenda a ride mid afternoon after her shift was over. When I dropped her off at her place, she asked me in and left me waiting for her in the living room while she took a shower. We were going to go grab a burger after she did. It ended up taking her forever and the couple of beers I'd had at the club began to take their toll on my bladder so I went looking for a bathroom. The only one there seemed to be was where she was taking her shower. The door was open and I hollered in "OK if I use the toilet?"

"Fine by me, just don't flush." she replied, then added "Then get your clothes off and get in here with me. I thought you were never going to come up!"

Needless to say I did as I was told and was rewarded with a wet and steamy fuck with her bent over and me taking her from behind. At one point one of her room mates showed up and pulled the curtain back to stand there and watch us, poised with her hand on her hip provocatively for a while before drawing the plastic back into place and disappearing. I came like a freight train right after that, pulling out and blasting my spunk all over Brenda's sweet little ass.

After that the sex was more conventional sleeping together vanilla sort of stuff but we still couldn't be away from each other for more than a day or two at a time without needing a fix of each other. When her monthly visitor came she actually set me up with a friend of hers one night to make certain I stayed a happy camper.

By late August she had moved, to a nice townhouse up near the lake that she shared with two other girls. A few doors down lived a stunning young brunette that she developed quite an interest in but seemed to not be able to get past first base with regard to any form of physical of amorous connection. This girl was smoking hot, but seemed to be hopelessly heterosexual which frustrated Brenda immensely. She was pretty much accustomed to getting just about anything she wanted sexually whether it involved a man or a woman.

To further add to her frustration, she had been bugging me to try going drag sometime. I'm of slender build and that summer was sporting long hair, as in past my shoulders and worn generally in a ponytail type long. For some reason she just got it in her head that I'd look good in a dress. I didn't find the idea appalling, but I wasn't particularly interested either. However, she kept bringing it up.

One night after a number of adult beverages she got me to agree to try it for her. I decided to push the envelope a little further and added a component to the scheme that would hopefully not only satisfy her fantasy to see me in a dress but maybe to push things over the deep end with her brunette friend.

Brenda shopped for me, picked out what she wanted to see me wear for the evening we had chosen. We agreed on a time (ten PM on a late August night) and I was to come to her place dressed as she desired. She would have invited Connie (the brunette) over and I would show up. Crazy, I know, but as I said, it was after a fair amount of libations.

That afternoon I showered and shaved. I shaved my legs completely smooth, shaved my ass, and trimmed my pubes down to a neat little triangle. I shaved my chest hair off as well. It felt different, but that was about it.

She had made arrangements for me to visit a hairdresser friend of hers who had been let in on the plan. She cut my hair a bit and styled it, then after I shaved my face one more time, she applied makeup and then showed me how to touch it up for later. I can't say I was the most beautiful "girl" in the world, but I'd say I was more attractive than a lot of women I've met once I was all dolled up.

Around nine fifteen I changed into the outfit Brenda had selected for me. I squeezed myself into a black lace bustier with no bottom, but with garter straps that dangled down in front and in back then pulled on a pair of sheer black stockings with lace tops that I clipped the garters to. A short grey crepe wrap skirt was added and then one of my simple black sport coats. The finishing touch was a pair of black pumps with moderately high heels. I checked myself out in the mirror and thought I looked pretty damn hot.

By twenty minutes to ten I was in the car and headed for Brenda's place. It was a beautiful summer evening and the sun had just disappeared, twilight was turning to darkness. Arriving at her complex just before ten I parked the car, took a deep breath and stepped out of the car.

Holy shit. That's when it hit me. I'd been playing along up until then because it was what Brenda wanted, but when I closed the car door and stood there out in the open I found myself getting oddly aroused. There was a slight breeze and I felt it wander up between my legs and caress the insides of my smoothly shaven thighs. Wow.

The walk to her unit took a couple minutes as I threaded my way along the winding sidewalk that led between the clusters of buildings. There was an occasional post lamp that illuminated the path and a few residents had front lights on. I could see lights in windows and I thought there must be people peeking out to see who was clicketty clicketty walking past. It was all very stimulating and I could feel my heart racing before I neared her door.

I rang the bell and after a bit heard the sound of high heels on wood flooring on the other side of the door. It opened and there she stood in silhouette. I stepped inside and my eyes fought to adjust to the brightness of the interior lighting.

Brenda was dressed as I had requested, a sheer black teddy with high cut legs and a thong back. She looked sensational. We embraced and she planted a deep long hard kiss with a lot of tongue involved on my painted lips. It seemed to go on forever, a kiss like I'd never received before from anyone. My hand wandered downward and fondled her bare asscheeks and she pressed hard against me.

When she finally let me breathe again we stared into each others' eyes for a moment, then I glanced around the room. Over on the sofa sat Connie in a pair of jeans and a T, mouth agape and eyes wide.

"Good to see you baby." Brenda said, "Let me take your jacket."

I unbuttoned it, slipped it off and handed it to her. She proceeded to do a one-eighty and then pranced across the room to drape it across the back of a chair in the dining area, her ass doing a lovely sashay as she did. When she turned to return to me, I unclasped the wrap skirt and peeled it off.

My cock sprang to full attention once it was released. I dropped the skirt to the floor and stood there with hands on hips wearing only the bustier, stockings, and heels as she strutted her way back to me. It felt exquisite to stand there like that occupying a realm somewhere between genders and from the delirious look on Brenda's face, it was turning her on big time. Connie just sat there, I guess in kind of a state of shock.

When Brenda reached me again she slowly sank to her knees and stared directly at my manhood examining it as though she'd never seen it before even though she'd been up close and personal with it quite a few times. Placing a hand on each of my thighs she drew them toward each other coming to rest with three fingers and a thumb on each hand delicately grasping each of my swollen gonads, the tips of her long painted nails scraping slightly against my scrotum and behind. Her tongue emerged from between her lips like a little erection of her own and using the tip of it she gingerly touched the slit in my engorged cockhead where a glistening bead of precum had oozed its way out.

Still holding my balls, she opened her mouth and slowly, seductively wrapped it around the fat mushroom knob in front of her. Once it was firmly ensconced in her hot wet mouth she pressed forward, taking more and more of the shaft in as well until she could take no more. She began a slow sensual movement that took her mouth up and down the hard shaft as she continued to fondle my boys. My hands went to her head, urging her not to stop and I began to rock my hips back and forth in a rhythm that corresponded to hers.

I glanced at Connie. Her mouth was no longer hanging open like a flytrap, but her eyes were still wide open in amazement that this was going on just ten feet from where she sat. I decided it was time to ramp things up a bit. Pulling my cock from Brenda's mouth, I put my hands on her shoulders and guided her to her feet.

"Take off the teddy." I instructed.

"Yes dear." she said sarcastically.

As she slipped it down and then off over her shoes, I sauntered toward Connie, my rigid dick bouncing and wiggling as I did. I stopped right in front of her and motioned for Brenda to come over. She did, her now freed tits jiggling much as my cock had. Her pussy was now fully on display, adorned only by a thin landing strip of pubic hair. When she reached us, she again went to her knees and this time my cock went immediately into her eager mouth. She leaned over against Connie's knees and rested an arm on her thighs as she focused on my member.

Connie's mouth was again open, this time not in surprise or shock. This time the look on her face was one of desire, craving some of what Brenda was getting. I reached for her hand that lay on the arm of the sofa and guided it to the cock that Brenda was so fervently attending to. Brenda backed off so that Connie could get a good grasp and Connie began stroking it, her eyes now filled with lust.

I placed a knee on the arm of the sofa and leaned over, bring my manhood to within inches of Connie's face. She continued to stroke it and then it happened. She leaned forward and took it in her mouth, taking right up where Brenda had left off. A moment later I felt a hand reach between my legs to play with my balls. Looking back I saw Brenda using her other hand to stroke her slit and then her middle finger disappeared deep inside her quim.

A few minutes later we pulled Connie off the sofa and separated her from her clothing. Brenda and I took turns going down on her before I got her on all fours and mounted her doggy style. Brenda again played with my jewels while I fucked away and then they swapped positions. After a while it became a blur of positions and combinations, but believe me, we left none untried that night. It went on for several hours.

One thing I do remember clearly was my first orgasm of the night. I had just been inside Connie missionary style and pulled out only to have Brenda grab my crank and start jerking away on it, causing me to blow my wad up the front of Connie. She gave a giggly shriek as I blasted a big load all over her, some of it even hitting her in the face. It didn't stay there long, as Brenda dutifully licked every last drop from her. At another point I came inside Connie and Brenda sucked and licked away at the resulting creampie.

It was a wild night and certainly one to remember. Unfortunately there was a downside to it as well. The two girls got so connected that they became an item and I ended up the odd (man) out. I haven't been involved with another woman since who has been into the drag thing, so there was no repeat performance. But it did open my mind to a whole different sort of appreciation for other peoples' kink.