My Story


Well, I have to say, the feedback from my first story has been amazing. There are so many people with similar experiences and or desires. I had debated telling my story for almost ten years and never thought I'd be continuing after my first installment recently but I have been so encouraged by the 99% positive response and many thoughtful letters. Thank you for the positive and to the one anonymous critic from Australia, Literotica is a sex site so why are you on it if it offends you so.

Anyway for those of you who would like to catch up you are welcome to read my story "First Time "as that is where I will begin this story.

After our first encounter which basically evolved from being my first sexual experience with men to a gang rape, everyone involved agreed to get tested. I would fully encourage everyone who participates in these activities to insist on this. Preferably before the encounters. I would also suggest testing for everything be done from HIV to Gonorrhea to the ones you don't think of like Hepatitis.

Well, no more lecturing. I will describe myself as a lonely businessman that frequently travels yet stays home a lot when not traveling. I used to live in Texas where these events occurred but I left for a cooler environment in the Pacific Northwest where it's been difficult to find men again. Oh, I cross-dress. I love dressing from slutty to classy, always in seductive lingerie, stockings, heels, wigs, breast inserts and if a dress is appropriate, ok. When dressed I go by Lisa.

The guys from my first experience came back negative and it turned out Walter, one of Robins "dates" was a doctor in Dallas and was willing to do the testing for everyone at only the cost of the Lab work which was great. Everyone agreed to meet regularly for sex nights and share cost of a room or meet at someone's home. Our next encounter was the following month at Mike's home.

We three girls were to be the entertainment and now that everyone was known to be clean there was no anxiety. Plus I was no longer a virgin and I knew I could take whatever they had in mind. Mike told Jan, Robin and I to come over early on Saturday and get ready so we decided to meet at his house around two that afternoon.

Jan it turns out had to leave on business, so as before there where only to be two of us "girls" Me and Robin this time. As before we surged ahead on our mission. We spent the first two hours in the tub cleaning each other. Robin thought I was spending too much time with the hose in her rear. She didn't realize it but there would be allot of other things in her rear before the night was over and she'd be glad it was clean. After a thorough cleaning inside we bathed, shaved and oiled ourselves outside till we were both silky smooth. We spent another hour applying makeup. Robin went for the slutty whore look. I went with subtle earth tones and tried to look classy, to go with the lingerie I had in mind.

Robin chose a black ensemble, much like I wore the first time. Black corset with black seamed stockings, 4"pumps and a short wrap around blonde wig, I wore a flesh tone nylon top that gave an opaque shadow of my D-cup wiggly breasts. A gray boned lace up Victorian corset with eight garter straps that held up some shimmering gray fashion stockings with a dark welt around the tops. I wore gray 5" stiletto's for my heels and my long wavy blond wig. Robin wore a black tight form fitting micro dress and I wore a dark blue wrap around knee length that tied in the middle with a long slit up the front and low front that showed my cleavage.

Once dressed, we went downstairs and had a drink with Mike as easy listening jazz played in the background. Sitting on the sofa the slit in my dress opened clearly showing my crossed legs sheathed in stockings. Robin's micro dress allowed an ample view of her stocking tops as well. The men began arriving, all within about 15 minutes. As everyone sipped on drinks the men all reminisced about our last encounter and complemented me on my abilities.

Finally someone suggested Robin and I get unwrapped which we both were happy to do. I picked Tim to make eye contact with as I slowly untied my dress tie and let the wrap fall to the ground. I stepped toward him with my arms around his neck and swayed to the music. I never broke eye contact as I moved in circle around him. After circling him I danced and presented my backside to him lightly rubbing his groin with my naked rear. Then I turned and kneeled still looking up at him, unzipped his jeans and fished out his cock. I had found during our last encounter that Tim had the largest cock in the group. About 8 or 9 inches long. Impressive in length but incredible in girth. A bow upward in the last two inches with very prominent features like veins and a thick muscled tube up the underside.

As I kneeled at his feet I began greedily slurping and sucking his amazing cock, all the while looking up at him with my eyes. His penis stiffened significantly as he approached orgasm. I kept my mouth firmly engulfed with his tool using my fingers to stroke the lower portion of his amazing cock. I could feel the pulses begin and I took his semen, allowing my mouth to fill one convulsive squirt at a time. I not once broke eye contact with my lover, making love with my eyes as well as my mouth. After he began softening I let his dick slide from my mouth pulling the sperm from his tissue. I tilted my head back and parted my lips playing with the semen with my tongue, allowing Tim and the men either side of him to peer into my mouth then I swallowed the entire load and finished by licking my painted lips and asking who was next.

I had four more cocks thrust in my face. I took one at a time giving each the complete attention of my mouth, lips, tongue and eyes until they each deposited their creamy loads in my eager mouth. Robin satisfied three of the guys and had to wait as I finished my fifth.

Afterwards the guys lounged in the living room and recovered from their orgasms. Robin and I pulled up a large padded bench in the middle of the room. I lay down on my back and she straddled me. We each began blowing the other in this position.

Soon someone lifted my head putting a strap under it and wrapping it up around Robins hips and tied it off. Another strap was fished under my hips and tied around Robins neck, tight. We couldn't pull away from each other's cock if we wanted to.

My legs were pulled up and the guys on either side held them in place firmly using the heels of my stilettos as handles. Looking up I saw four vibrating eggs being inserted in Robin's rear. Then I felt something I assumed were eggs sliding in my rear.

Then I saw a cock line up and pierce Robin's sphincter. I felt the same thing happening to me. Knowing Robin was seeing a cock penetrate me at the exact moment a cock was penetrating her was an awesome experience. I watched as her anal ring stretched tightly around the invading cock then the ring pulled inward as the cock slid in without stopping.

The eggs began to vibrate and Robins cock, within seconds stiffened then pulsed then exploded in my mouth filling me with yet another load of sperm. Robin's contractions caused the dick in her to thrust forward. I raised my fingers, cupping the testicles of the man fucking Robin and feeling the ejaculation pulses at the base of his cock. I knew at that instant, Robin's insides were being coated with slick cream from deep within the man breeding her. I soon felt the man in my rear explode filling me with his seed as well. Both dicks were replaced with fresh ones.

The men didn't fuck us hard. They simply rocked a little letting the vibrating eggs and the tightness stimulate them to orgasm. The vibrating eggs and the thick penis probing me as well as Robin swirling her tongue in my tiny opening caused me to shoot my load off in Robin's mouth. She couldn't pull away anymore than I could so she had to take my load. I felt the contractions in her throat so I knew she was swallowing.

As the men slowly fucked us and the eggs relentlessly vibrated on our prostrates we each came once more. I could feel the warmth and wetness increase each time one of the cocks exploded in me. The close up view I had of Robin impaled on one hard cock after another was extraordinary.

When Walt who has a penis with an amazingly plump purplish head fucked Robin he pulled out numerous times till just the head remained in her. As it would pull out I could see her anal ring distend outward, being pulled by the swollen head. After the guys had all had their pleasure with Robin and I they sat back and leered at her and me, still bound and mated cock to mouth. Both our dicks were soft and fit easily but we were lazily tonguing each other's spongy head. The guys watched for awhile but guys being guys they decided to continue to push the envelope with their captive playmates. I felt my stocking encased legs being lifted again, pulled up till my knees touched my breasts, the guys having discovered I'm quite limber.

I again felt probing with fingers, pulling the creamy wetness from inside me. I saw fingers begin to probe Robin as well. Fingers pulled and stretched and massaged her opening with slimy creamy semen till it resembled a sloppy wet pussy. I felt myself being obscenely stretched. I knew I was destined to be filled with a fist.

Robin had a close look at what was happening to me and when she felt someone pushing their hand in her she began a futile protest. She was attempting to voice a "no" with my penis in her mouth. As the hand continued to push she began to tighten her jaw and more importantly her teeth. I reminded her of the situation by grating my teeth on her cock. She relaxed her bite but still remained tense. I sucked vigorously on her cock and she relaxed. Pressure continued to build. Whoever was pushing into me had a much larger hand than before.

Finally relief coupled with incredible fullness. The fist began to rotate and swirl around in me. I watched, mesmerized as Robin's pussy like anal ring distended incredibly as the fist penetrating her ever so slowly slipped in her. Once in, the hand continued deeper slowly, slowly and even slower. Pulling out a bit then continuing until I saw the elbow. Absolutely incredible. The fist in me had begun to pull out and push in till he was coming completely out then completely in. Fucking me with his fist. Then he made a fist in me and worked it in a jabbing in and out motion rubbing my prostrate once again. My penis, though completely soft began to ooze semen in what can only be described as a prostrate orgasm. Robin to her credit sucked it down and continued to suck literally drawing a vacuum from inside me. Someone turned on the eggs in Robin and I reciprocated her oral technique and she moaned and began sobbing as cum flowed from her limp penis. She had hard pelvic contractions as I continued to pull a vacuum trying to drain her.

The guys pulled their limbs from us and released our bonds. So exhausted we remained coupled. The men helped Robin off me and assisted me to a standing position. She and I hugged and held each other up as the men gave us a round of applause.

If the response is as encouraging as before I will continue to write. To those that have responded, I thank you so much.


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bycdandie© 7 comments/ 41256 views/ 6 favorites

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