Much happened in the next twelve months following that first session with my ex and her new partner: Ann began divorce proceedings which I didn’t contest, I financed myself into another home, and Ann, David and I met for two more sessions of torrid sex. These sessions were pretty much replays of the first; I would first screw Ann thoroughly through at least two climaxes, and then she would watch avidly as I serviced her partner David, playing with herself and having a further orgasm as she watched us having a little man to man fun. Both these two latter meetings occurred after Ann had phoned me each time, saying that she and David were hungry for more of my big cock. I was always happy to oblige, as Ann was still one of the hottest women I had enjoyed. So I was a little surprised when David phoned me out of the blue several weeks ago and asked if we could meet for coffee, saying that he had a friend he wanted me to meet. Pressed by me for more details, David admitted that he had confided to a younger work colleague some of the things that he and Ann and I had done, and as a consequence the colleague had asked for an introduction. Intrigued, I agreed, and we made a date for the following week.
David and his friend met me at my usual café just as I was having my coffee delivered to my table. Having placed their orders they joined me, and David introduced his friend Ash. I was a little surprised, as Ash was looked to be in his mid-twenties, and was consequently about twenty years younger than both David and I. He had unusually smooth skin, and I noticed that his hair, nails and attire were fastidiously tidy. We chatted over our coffee for several minutes until David had drunk his and he excused himself, saying he had to get back to work. As he left the café, Ash moved a little closer and told me in lowered tones that David had initially hinted at, and then later admitted to Ash that he and Ann and I had enjoyed a number of threesomes. David had shared this information after Ash had told David that he and his wife had recently talked about a experimenting with a threesome. I could feel my cock swelling comfortably as Ash related this, and when he asked if I would be interested in meeting his wife I readily agreed. We exchanged mobile phone numbers and Ash promised to call me the following day after he had spoken about it with his wife.
As he had undertaken, Ash phoned me the following morning, telling me that he had talked with his wife Melanie, and she first wished to meet me alone before agreeing to a threesome, to which I enthusiastically agreed. I was flexible regarding times, as much of my work was undertaken in the evenings, and so it was settled that I would visit their home at two the following afternoon to meet Melanie, or Mel as David told me she preferred to be called.
Not having fucked in forty eight hours, and primed by the previous day’s conversation with Ash, I was feeling unusually horny when I knocked on the door of Ash and Mel’s home the following day. I response to my knock a voice from within called out to me to let myself in, saying that the door was unlocked. As I closed the front door behind me Mel stepped into the hallway, and with my astonished eyes I could see why she hadn’t wanted to expose herself on the doorstep. She was a white and pink vision of lace and silk; exquisitely made up, with her thick blonde hair cut in a short bob, the ruched front of her see-through white blouse not quite concealing her white lace bra, while her flared pale pink skirt was so short that it revealed the tops of her smooth thighs and the white suspenders supporting her white stockings, as she teetered before me on high heeled pink shoes. She was tall, almost as tall as her husband I guessed. My cock throbbed to an almost instant erection at the sexy sight before me, a fact not lost on Mel as she gave my crotch a meaningful stare before giving a throaty chuckle and saying in a low, husky voice “Well, I’m pleased to meet you too, Doug!”
I began to stammer an apology, but she chuckled again. “Don’t be silly Doug, I dressed especially for you. I’d be disappointed if you didn’t like my outfit”
Swallowing the lump of excitement in my throat I asked “Do you dress like that for Ash?”
“Oh yes”, she replied, “often, and he likes it too!”
“I’ll bet!” I thought to myself, wishing that I could reach down to adjust my cock, which was trapped in my underwear and was so hard it was painful.
As if intuiting my problem, Mel teetered closer, reaching to cup the bulge in the front of my trousers. “Poor Doug! Does that big cock I’ve heard about need to be let out?” her slender fingers massaging my swollen cock as she watched my eyes intently, her heady perfume filling my nostrils. As if having come to a decision, she gave a little nod and sank to her knees, unbuckling my belt and unfastening my trousers, pulling them and my briefs down my thighs. The air felt pleasantly cool on the heated flesh of my cock as it sprang from its confinement. “Oh my, that’s a big one!” Mel murmured huskily, “Is that all for me?”
Almost choking with excitement, I responded hoarsely, “You bet sweetheart, as often as you like!”
I felt Mel’s warm breath gust over my cock as she leant forward to take my heated flesh into her mouth. My ex-wife Ann had been the best cocksucker I had known, but Mel was every bit as good, and where Ann would fairly quickly get greedy to have her own hunger satisfied, Mel seemed content to continue to stimulate me. I was almost at the point of losing control when Mel suddenly stopped, letting my straining wet cock spring from her lips. Looking up with a wicked grin she murmured “What a bad hostess I am! Here we are, still in the hallway and I haven’t invited you inside properly!”
My voice strangled with passion, I tried to assure her that she could finish right there what she had started, but she rose to her feet and reached for my hand, tugging me up the hallway. Clutching my trousers with my free hand I hobbled after Mel into the lounge, where she pushed me into a chair. I sat somewhat dazed, with my trousers still around my knees, my erect cock wet with Mel’s saliva as I watched her fill two glasses with white wine from a bottle she took from a cooler on the coffee table. I was accustomed to taking the lead in sexual situations, but Mel seemed about two jumps ahead of me.
Teetering back to me on her crazily high shoes, Mel handed me a glass before gracefully folding to the floor beside me, extending one hand to tease my swollen cock with her fingernails as she sipped her wine. Taking the glass from her lips she breathed huskily “Dave told me how Ann was always talking about your cock! I can see why!”
Giving a grunt of laughter I responded “She’d still be getting it regularly if she hadn’t caught me sharing it around!”
Giving me a wicked smile Mel countered “But then you might not be sharing it with me!” Taking a long sip of wine she put her glass down and moved between my knees, plunging her mouth over my cock. I groaned with pleasure at the exquisite shock of the mouthful of cold wine on my cock.
Bending forward as Mel worked on my cock, I fumbled for the buttons on her blouse, but before I could open it Mel released my cock and pulling away from me stood, saying “I’m not very big there, and anyway you haven’t seen my special panties yet!” Turning away from me she pushed her pert backside back at me, at the same time flipping up her brief skirt. Beneath her skirt she wore a frilly pair of white lace panties, a style I think are called ‘boy shorts’, except this pair were split from the waist to the crotch, held together with three little white satin bows, so that the shadowed cleft and creamy flesh of her smooth buttocks peeped through the openings between the bows.
My heart was pounding, my breath short as I gazed at the entrancing sight. “Do you like them Doug?” Mel whispered, looking back at me. Choking on words that would not leave my throat I nodded vigorously. “Do you want to undo the bows?” Mel breathed sexily. Sliding from the chair onto my knees I pulled Mel’s hips closer. With trembling fingers I untied the first bow, exposing more of her buttocks, bending forward to press my lips to the cool flesh of her smooth globes as I fumbled the next bow undone.
Taking my lips from Mel’s smooth buttocks I whispered hoarsely, “Are there more bows at the front?”
“Yes!” Mel whispered back, “But don’t you like my bottom?”
“Of course!” I choked.
“Show me how much!” she breathed, waggling her hips invitingly. In response I grasped her smooth mounds in both hands, spreading them to rain kisses inside her cleft before licking up and down its length, pulling her cheeks even wider apart to tongue the pursed pink pucker of her anus.
“Oh yes!” Mel groaned, “You do like it! I wanted you to like it! I want you to fuck me!”
“Turn around then!” I whispered hoarsely.
“No, give it to me that way, the way you did Dave!” she responded urgently.
Disconcerted, but still highly excited I told her, “But I need lubricant!”
“In the silver box on the coffee table,” she told me in an urgent whisper, “and condoms, if you want them!”
Crawling past her and reaching for the box I told her “I’d rather feel you on my cock!”
Taking the tube of lubricant from the box and uncapping it I turned back to Mel, who had moved to the chair I had recently vacated and was bending forward over it, bracing her arms on the chair with her hips pushed back towards me. Spreading her smooth globes with the thumb and fingers of one hand I pressed the neck of the tube to her pink anus, forcing a good squirt of lubricant in and around it. Standing, I kicked off my trousers and briefs and moved closer to Mel. Feeling my hot knob probing the cleft of her buttocks Mel looked back at me over one shoulder. “Be gentle with me Doug, I’ve never had one that big before!”
Telling her “Don’t worry sweetheart, I’ll take it easy at first!” I moved even closer. Parting her buttocks with both hands I guided my knob to her pucker and pressed forward. Despite Mel’s concern my knob initially slipped partway in quite easily, but I heard her give a little gasp as the resistance increased. “Breathe deep and push back!” I urged, keeping a gentle yet steady pressure on my cock. Mel gasped again as the elastic muscle gradually yielded and my knob slipped inside her.
The first time with any sexual partner has always been particularly exciting for me, and on this occasion the heat of Mel’s rectum on my knob and the exquisite tightness of her anus on my shaft were focussing my mind solely on the fabulous feeling of taking this beautiful young woman for the first time, as I slowly worked my shaft ever deeper into her slim buttocks. Especially stimulating was the fact that while she was essentially fully dressed, Mel’s hips were effectively bared to me for my lascivious pleasure. My hips pressed against Mel’s firm rounded buttocks, and I was all the way in. Withdrawing fractionally, I began a measured, steady pumping of my cock in Mel’s tight anus, initially only tiny movements but gradually increasing the length of my strokes as Mel’s anal muscle slowly spread to accommodate me.
“Oh Doug that feels wonderful!” she moaned, beginning to push her buttocks back to meet my thrusts. Grasping Mel’s hips I began to pull her hips back to match the slowly increasing rhythm of my strokes.
“You’re so tight!” I gasped, “It feels so good! I’m not going to be able to hold back!”
“Don’t hold back! Let go Doug, let go!” It was all the encouragement I needed. Thrusting ever more forcefully as the familiar tingling and straining sensation built in my groin, with one last urgent
jerk of my hips I buried my cock deep in Mel’s rectum, holding her hips tight to my belly as my cock throbbed and spurted inside her.
With Mel still kneeling before me I stood panting, our bodies locked together until my cock began to soften. Releasing Mel’s hips I eased myself from her, and half turning she collapsed forward into the chair, smiling happily up at me. “Phew! You know how to show a girl a good time!” she giggled, giving my still swollen but limp cock a meaningful stare. “Is he going to sleep now?”
“Not for long darlin’!” I told her, “Not around you!” asking “Where can I have a quick wash?”
Lifting herself from the chair she took my hand and led me from the room and across the hallway to the bathroom. “While you clean up I’ll use the ensuite in the bedroom.” she told me, indicating towards the end of the hallway, “Don’t be too long! I’ll be waiting!” Giving me a wink and a lascivious smile, she teetered up the hall as I watched until she disappeared into the bedroom.
Towelling off after a quick shower and leaving the rest of my clothes in the bathroom, I made my way up the hall to the bedroom. Sprawled in the middle of a king-sized bed and still dressed, Mel smiled coquettishly up at me as she patted the bed beside her. My cock began to swell and stir at her obvious invitation, swaying as I stepped towards the bed. As I climbed onto the bed, Mel grasped my cock, pulling me towards her. “Mr Sleepy’s waking up!” she giggled, “Let’s see if we can’t get him ready to party!” Pushing me onto my back she moved between my legs, pushing my knees back and up. Her hot mouth descended on my rapidly filling cock, the fingers of one hand worming between my buttocks to stimulate my anus as the other hand massaged my balls and the base of my shaft while her talented tongue and lips teased exquisite sensations from my knob as my cock swelled to full erection.
Over the next half hour or so Mel expertly demonstrated her oral skills, several times bringing me close to orgasm before easing back and taking me off the boil. Several times I reached for her, wanting to pull her over me in order that I could reciprocate, but each time she evaded my reaching hands and distracted me by squeezing my balls or fingering my anus. However when I sensed that I would soon want to seek release and explode in her mouth, I tried to sit up, reaching to try to pull her up to me, but lifting her head from my cock and putting a hand on my chest she pushed me back onto the bed. “Later Doug!” she urged huskily, “Let me taste you first!”
With a sigh of frustrated resignation, I lay back. This time when my hips began to surge to meet the rise and fall of Mel’s lips on my shaft she increased the activity of her mouth and busy fingers, and with a groan of release I discharged my flood of hot ejaculate into her suctioning mouth. Swallowing greedily, she milked my cock as it slowly lost its rigidity, until she let it slip from her mouth to fall wetly back on my belly. Licking her lips suggestively, Mel flashed me a lewd smile before pushing herself up onto her knees and crawling up the bed to nestle beside me as I reached an arm around her to cradle her close.
I was temporarily sated and would have been happy to lie back and doze, but the combination of the warmth of Mel pressed to my nakedness, her heady perfume and the sensation of her fingers delicately fondling my cock and balls soon had my limp cock stirring to life once more. Cooing her appreciation at my recuperative ability she twisted around to take my semi-erect into her mouth. I lay back, enjoying the sensation of my sensitive cock slowly responding to the stimulus of Mel’s lips and tongue teasing me to hardness. As she lay across my waist, her mouth busy on my cock, I reached to caress her shoulders and back, unable to touch beyond the swell of her buttocks. Finally, my cock restored to throbbing hardness, and with a desire to sink it into Mel’s warm, wet flesh I took my hand from her shoulders to reach beneath her cheek, stilling her mouth’s movements on my cock as I pushed myself up on one elbow.
“Come on darling!” I told her, “I want your pussy!”
Turning to look at me, her face flushed, she responded “Oh Doug, I want you too!”
Rolling over and drawing her knees beneath her, she turned to present her buttocks to me, wiggling them in an open invitation. Getting up on my knees I grasped her hips, pushing her onto her side and grabbing her ankles in both hands to spread her legs wide I rolled her onto her back as I moved between her thighs. I would have preferred her naked, but was gripped with an urgency to claim her cunt. Resting her stockinged legs on my shoulders I pushed her short skirt up, barely registering her unusually prominent pubic bulge as I reached to release the bows holding her panties together at the front. However my passionate urge to mount her was halted as the panties gaped open to reveal not the wet and open cunt I anticipated, but tight hairless balls and a slim and equally hairless erect cock.
It was not just the startlingly unexpected appearance of the male appendages that caused my desire to flag, but the fact that the beautiful, sexy and exciting young woman who I had enjoyed so immensely in the last hour and a half or more had so suddenly been revealed as a man. My jaw must have dropped as fast as my erection had died, for Mel, or whoever she was gave a throaty chuckle, reaching up to caress my cheeks as she told me “Poor Doug, what a shock for you! But don’t you see, you’ve already had my pussy!”
Stammering in my consternation, I asked who he was.
“Don’t you know Doug? Don’t you recognise me?” and he pouted in mock annoyance.
Dumbfounded, I shook my head. “We haven’t met!” I croaked, my mouth dry.
“Yes we have Doug!” he told me, “It’s Ash, or as I prefer when I’m dressed like this, Ashleigh!” spelling out ‘leigh’ but pronouncing Ashleigh as Ash-Lee.
“Well, who is Mel?” I stammered.
Telling me, “Poor Doug! Lie back and I’ll go and get our drinks and then I’ll explain.” he pressed me gently back onto the bed, rolled over and slid from the bed to pad from the room. I lay back, stunned, my mind whirling. Ash, or Ashleigh, came back into the room with our glasses of wine and the bottle.
Lifting up on one elbow I took the glass proffered to me and took a long gulp of the cold wine, easing the lump in my throat. “Are you married? Does Mel exist?” I queried shakily.
“Yes Doug, I am married, and to Mel, and she does want to meet you, but I wanted to meet you alone first!” he told me. “Do you want the long story, or the short one?” he continued.
Taking another long sip of wine, slowly regaining control of my senses, I told him “You’d better tell me it all!”
“I guess it goes back to when I was little.” Ash began. “I was the youngest child in our family, with four older sisters who doted on me. I was never alone and even slept with them in their beds on occasions. They thought that it was fun to dress me up as a girl at home, and sometimes I went out with them dressed as a girl at Halloween. But by the time I hit my teens they had all left home, married or gone flatting, although they were often at home. I didn’t have the desire to dress as a girl again until after I married Mel.” he told me. Giving a wry smile he continued, “Because I work as a company rep I’m often home in the afternoon if I finish early. One afternoon I was hanging my suit up when I saw a party dress Mel had put out but forgotten to take to the cleaners. It looked so pretty that I wondered what it would look like on me and tried it on. I tried putting on some makeup and then I put on a fun wig of Mel’s.”
“Is that it you’re wearing?” I interrupted.
“Oh no!” Ash responded, “This is an expensive one. But even in the fun wig I looked like a woman and it made me feel very sexy. I began trying on Mel’s clothes and walking around the house dressed up when she wasn’t home. However one day she came home early and surprised me. By then I was better at putting on makeup and at first she thought that I’d bought a girl home. When I told her it was me she began crying. She wanted to know if I was a transvestite or something, and if our marriage was over.”
Taking a long sip of her wine she grinned at me a little ruefully. “It took ages to console her,” Ash continued, “and when she had calmed down and asked me what I felt like when I dressed up, I took her hand and put it up my dress so that she could feel my erection. We ended up having very passionate sex, more so than ever before, and after that Mel began helping me to dress up, even helping me choose clothes and shoes. I bought this wig and another brown one, and a couple of times we’ve even gone out on the town together and had fun flirting with guys.”
“That sounds risky!” I interjected, “Hasn’t that ever got you into trouble?”
Ash laughed, “We’ve had to sneak out the side door in a couple of pubs,” he giggled, still sounding as Ashleigh, “but nothing we couldn’t handle.”
Ash was still acting and sounding like Ashleigh, his other persona, and as such was very attractive, and although I was now aware that a lot of his gestures and female mannerisms were a little contrived, I still found Ashleigh, as I had begun thinking of him, sexy, and was beginning to think of him as a woman again. In spite of my earlier shock my cock had slowly swollen, although it was by no means erect. Ever observant, Ashleigh noticed and looked at me slyly. “Did you like the trick with the wine?” she asked archly. I nodded vigorously, my throat tightening with excitement. “Would you like me to do it again?” Again I nodded. Taking a mouthful of wine she set the glass down and leant over to suck my stiffening cock into her mouth. As before, the stimulus of the cold wine and her suctioning lips on my heated flesh rapidly brought it to full erection. Lifting her mouth from my cock and looking up at me from beneath her long eyelashes she asked huskily “Do you want my pussy again?” In response I rolled over and got up onto my knees, reaching for her.
Passing me a tube of lubricant she took from a bedside drawer, Ashleigh rolled onto her back, her legs wide and knees drawn back in an open invitation. Despite the smooth erect cock and tight balls framed by the gaping panties, the sight was highly erotic. I spread lubricant on my cock and shuffled on my knees between Ashleigh’s smooth thighs. Raising her legs she hooked them over my shoulders, lifting her hips to meet my probing cock. I mounted her, savouring the exquisite dragging sensation of her tight anus on my shaft as I slowly slid into her. “Oh God Doug that’s wonderful!” she moaned.
“Am I really the biggest you’ve taken?” I asked, my throat tight with excitement.
“You’re my first man,” she gasped, “Mel’s used toys on me but I’ve never had a man before!” This information served to further arouse my already heightened passion. As our fervour grew and our bodies plunged and rose with increasing urgency, Ashleigh flung both arms around my neck, pulling my mouth to hers, and for the first time ever I shared a long and passionate kiss with a man as our bodies surged to a mutual orgasm.
Holding one another tightly until our breathing eased, our mutually clasping arms slowly relaxed and I eased myself from Ashleigh. Her panties and belly were wet from her ejaculation, which our heaving bodies had also forced up over her short skirt, crushed over her chest by our passion. Easing her legs from my shoulders Ashleigh pushed herself back up the bed to lean against the headboard, reaching for her glass and taking a long sip of wine as she pretended to fan herself with one hand. “Phew!” she announced breathlessly, “That was something else!” Suddenly giggling she told me “You’d better show Mel a good time like that or she’ll be jealous!”
I crawled up the bed to join her and took a refreshing mouthful of wine. “You were serious then,” I asked, “about a threesome?”
“Oh yes!” she responded, “It’s just that I persuaded Mel that it would be best if I checked you out first!”
To be continued.
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with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/crossdressing/ready-to-perform-part-two-all.aspx">Ready to Perform, Part Two – All Crossed Up</a>