As I sit here at my computer with my pants down around my feet it is difficult to keep my hands on the keyboard as I relate to you the events of that night. I am a mid-fifties cross dressing hetero-flexible male who likes to wear pretty women’s undergarments under my male street clothes. I also enjoy anal pleasures rooted in my interest in enemas. I travel a lot and have developed opportunities to meet similarly situated men wherever I go. I had done such a thing with one particular married cross dresser in Springfield, Ohio a couple times, ending up at my hotel room to play dress up and fuck and suck. He was shaved smooth while I retain my body hair to provide an interesting contrast to my feminine outfits. Our events always start out with a little douche of our holes using my bag or bulb and end up prancing about in an effort to retain the soapy water. Our enema dance usually results in semi-erect penises. Usually a suck whilst expelling is performed followed by a sperm enema with a flesh nozzle.

During our second such event he mentioned that he was wearing the panties his wife wore to work that day. He showed me her dried cunt juices on the crotch and I breathed their aroma in deeply. It was a perfect blend of cunt juice and ball sweat. As I was giving him a squeeze from my bulb he told me that he should be pretty clean already as his wife had used a strap-on dildo on him last night. I indicated that I felt he was a lucky man to have a wife to bone his ass any time he wanted. He corrected me – any time SHE wanted. He suggested that I should meet her sometime. I really had no exposure to swinging but he assured me it would be fine. We had our usual good time but continued to discuss bringing his wife into the mix. We agreed that on our next visit I would be introduced to swinging.

Two weeks later when I was in Ohio again we met for a beer. He called home and told his wife that I would like to meet her dildo tonight. Her response to him indicated she would be waiting for us with a special surprise. I followed him in my truck, driving to a suburban location a couple miles out of town. The single story home sat a good distance from the road and surrounding houses and had a tall wooden fence surrounding a perimeter near the home. We entered the fence through a gate next to the garage and continued down a narrow pathway to reveal a smaller perimeter privacy fence surrounding a patio. When we entered through that fence I saw two women in a hot tub on the patio. He introduced the blonde as his wife and she introduced the surprise - her long dark haired friend, Sammi. They both had no tops on as I watched their ample breasts swirl around in the turbulence of the agitated water in the tub.

After some small talk he indicated that he needed to go prepare for some fun. He disappeared through a sliding door into the house only to return a few moments later wearing a pink lace garter belt, nylons and a G-string over it all. Not a vestige of men’s clothing remained, his hairless chest covered with a pink lace bra. He held up high for everyone to see a very full enema bag with a long hose clamped shut to keep the liquid from escaping the long thick nozzle that was only inches from the ground. He asked who wanted an enema. I was of course going to volunteer but to my surprise Sammi rose up out of the hot tub first and indicated that he would like to receive one. Yes, he. As Sammi stood up the bubble filled water could no longer conceal that Sami had a lovely cock; very sizable when limp, no doubt helped by the warm water in the tub. Sammi was a transsexual. This was going to be an interesting night.

Sammi grabbed the hose, pulling the nozzle to his mouth and lubricated it with his saliva. Without hesitation the nozzle disappeared inside his body as my friend hung the bag from a hook on the patio umbrella that had no doubt been installed for that expressed purpose and probably used many times for such an event. When my friend released the clamp, Sammi indicated that the water was very warm and felt stimulating. Sammi positioned himself on the chaise lounge to allow the fluid to find itself deep into his bowls. As he rolled around trying to adjust to the filling my friend’s wife took Sammi’s penis into her mouth and brought him to an erect state. When the bag gurgled to empty Sammi was in ecstasy. As my friend withdrew the nozzle from Sammi he indicated that it was my turn next. I stripped when he retreated into the house, watching the unfolding blow job while Sammi retained his waters. I had on orange sheer crotch-less panties for everyone’s viewing pleasure. My semi-erect penis and scrotum nicely outlined by some black lace hung freely from the openings in the fabric. My friend returned with another full bag but there was no nozzle on the end of the hose.

Sammi stood up with an urgent need to empty his rectum foregoing any further oral pleasure from my friend’s wife. He strolled over to the edge of the patio and watered the flower box there with the clean discharge from his hole. With his wife now disengaged orally she began talking about using her strap-on dildo on my ass. I indicated to her that I may not be ready until after I get an enema, anticipating that I would receive the same oral treatment from her luscious lips as Sammi did during his enema. But she said that she had another surprise in store for me that night. She retreated into the house and returned carrying a strap-on dildo. There, tangled in the harness was a short section of rubber hose and an in-line squeeze bulb – this was no ordinary dildo. She told me that I was going to get an enema WHILE she fucked me with her strap on. Yes this was a dildo nozzle that I had heard so much about from everyone on Zity but this was the first one I could actually touch. Or more correctly – would actually touch me.

She climbed into the harness as her hubby fitted the straps to her curvy body. I was somewhat apprehensive about the size of the dildo as it was bigger than the cock of her husband, bigger than any real cock that has fucked me in the recent past. Sure there was the occasional monster vibrator I snuck from my mother’s night stand and shoved up my tender young ass, but that was a long time ago. Those events were almost enough to turn me away from any future anal play – well almost. Once it was in and vibrating me, I quickly changed my mind as I found it to be quite pleasurable.

The hose from the bag was now being fitted to the short lengths of hose with the in-line squeeze bulb connected in the middle that ultimately was connected to the base of the hollowed out dildo forming a penis nozzle. My friend began to spread a glop of a white greasy substance on the fat and long ersatz cock. I got on my hands and knees at the end of the chaise lounge and she strolled right into place behind me, the cock swinging from side-to-side as she did. My friend opened the clamp as she began to squeeze the bulb. The rubber cock began to ejaculate the contents of the bag through the tip of the dildo. She playfully aimed the spurting liquid at my anus to make sure she was on target and it splattered all over my ass. Another glop of the white greasy stuff was smeared on my crack and she moved in. I felt the tip of the dildo begin to spread my cheeks as she used the dildo to smear the lube up and down my crack. She instructed her hubby to stand next to me and spread my cheeks so she could get right in. He did as instructed and she pushed. I took a deep breath and tried to relax my sphincter. She backed away and continued stroking the head up against my sphincter – toying with me until she forcefully bucked once again with her powerful hips and the head popped in my body. She paused as I was somewhat in agony, my hole suddenly stretched to the large diameter of the intruder. As she sensed my pain subsiding she slid the balance of the shaft into my body. I could feel every bump and vein molded into the shaft of the dildo as it slid past my sphincter. Finally the rubber balls touched mine and I knew that I had just taken a ten inch dildo with a two and a half inch diameter fully up my ass. My pain soon turned to pleasure as the dildo rubbed against my p-gland. Those same bumps and veins that I felt entering my body were now causing my tight sphincter to almost vibrate as she picked up the pace of her stroking in-and-out. When I finally got my sphincter to lock open in the anal gape mode she began to squeeze the in-line bulb causing the enema to enter my rectum in spurts. The gape mode would not work for long as the pressure of the enema began to build in my bowels. Every pump of the bulb and thrust of the dildo pushed water deeper into my body – I was getting full very fast. I had to tighten my sphincter back up or risk making a mess. I leaked a little on their patio and my friend explained that it was alright, they would hose it down after I left – probably wash a bunch of cum down as well. Returning from expelling, Sammi had noticed my cock swinging between my legs with each of her thrusts and began to suck me. Seeing that he had sucked my cock till it was fully hard, he lay down in the chaise beneath me and guided my cock into his ass. Sami’s cock poked through the plastic weaving of the fabric on the chaise. The hips of my friend’s wife bucking against my ass drove my cock deeper into Sammi’s ass all the while the enema swirled around in my rectum. I was losing control, my body twitching wildly. Sammi reached beneath the chaise lounge and began to stroke his cock.

My friend moved from keeping my ass cheeks spread to sitting on the chaise facing Sammi and positioned his cock in Sammi’s mouth. He fucked Sammi’s mouth like it was my ass. All of the rhythmic thrusting was quickly bringing my friend’s wife to an orgasm as the base of the dildo pounded her clit. I was not far behind dumping my load in Sammi’s hot transsexual ass and Sammi pumped his hard cock one last stroke to ejaculate on the ground as my friend delivered his huge load that overflowed Sammi’s mouth and spilled on the chaise. I guess my friend was right – he would be hosing down the cum and enema from the patio that night because as my friend’s wife came she withdrew the dildo fully before I could clamp my sphincter back closed and a lot of enema waters shot out on to the bricks. We showered and relaxed the hot tub the rest of the night, planning a road trip with me in the next month or so.

My shoes are now sticking to the floor under my desk as I have completed recalling my tale for you. I dumped a load on the tile. Hope you find this tale interesting and experience something similar.

R. B.