Pleasuring A Mature Man

"My story of loving an older woman who shares me with mature men."

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I met Lauren while working at a vintage vinyl record store in New Jersey, just nineteen but already renting my own small apartment nearby. I tended to dress in black concert tee-shirts and slim blue jeans with flared bell-bottoms, much as my own mother had during her youth. Lauren, by comparison, visited my small shop in a petite floral dress that emphasized all of her feminine curves, complemented by high-heel pumps. She radiated natural beauty with rich red hair and porcelain pale skin, but it was her sensuality that attracted the attention of men and women alike. From the moment that she entered until finally approaching me with a question concerning a record recommendation, I found myself enchanted by her every subtle movement and the sing-song melody of her musical voice.

Lauren appeared to be the kind of woman I aspired to be, though twelve years younger myself. I often felt awkward and less appealing to handsome men. We became friends before she left with a selection of albums which I felt she bought merely to impress me, and by the time we shared our first dinner together, I realized that I was already smitten with her. At thirty-one, she possessed both the innocent appeal of a youthful woman, but also a distinct feminine ability to persuade anyone to please her simply for her special attention. I knew early on that I would never be able to resist her desires, and you need only view her photo in my gallery to understand why I describe her so.

Lauren is a young woman who inherited both her irresistible physical beauty but also an intellect and imagination to be a successful artist. I enjoy writing and sometimes play guitar with my close friends, but I have never considered myself to be especially talented or a uniquely attractive young woman. Lauren lured me into her lifestyle of living more comfortably than I could afford, lavishing me with gifts that enabled me to continue working for a record store and still manage luxuries that I never could have indulged in myself. She is a serpentine lover, such that her slender body is always slithering around my own when she makes love to me, embracing me in ecstasies which I had never experienced with a single young man whom I dated prior to our introduction to one another.

She was clearly popular with both men and women alike, explaining that her other affairs would never diminish what we shared together, but that she wasn’t one to resist opportunities to further explore her own sexuality. She was very convincing that she sincerely loved me, but that I needed to make a decision as to whether I could continue dating another woman who might occasionally share her bed with male friends. I didn’t feel any jealousy towards men who couldn’t stand to replace me in her life, but I wondered how her other relationships would affect our living together between two shared apartments. I didn’t have any reservations that concerned me, so we continued to enjoy our relationship, which grew stronger every day.

As I have said, my only prior boyfriend had been a young man whom I had grown up with. He and I shared an interest in music, sometimes playing in amateur bands or even with my own father and his musician friends. Our sexual experiences had been awkward at first, but then evolved as we came to better understand our own bodies and one another’s. When Lauren first suggested that I meet her friend Daniel, I imagined that the evening would alleviate any discomfort about her involvement with other persons. I agreed to share dinner with them at a favorite restaurant, then return to her apartment for a drink and maybe a movie. I hadn’t presumed that he might stay the night with her and send me home, or whether it would be him leaving as Lauren and I remained in one another’s embrace for the night.

Daniel was forty-one and distinctly handsome, but I hadn’t ever considered myself dating a mature man who was twice my own age. Lauren clearly had him wrapped around her little finger, always so sensual and the center of everyone’s attention. She had bought me a nightgown in black, with sheer stockings and matching black pumps for our formal dinner. I felt more attractive than my usual jeans and tee-shirt self, but nowhere near as alluring as Lauren appeared in a shoulder-less short-skirted dress and platform stilettos like you would see a dancer wearing on stage. Ample breasts nearly bursting through the supple cloth, and long legs sheathed in satin sheer, revealed her garter belts just above the hemline. I found myself equally enticed by her as Daniel clearly was throughout our dinner, and when we finally decided to leave for the apartment together.

Lauren poured drinks for Daniel and herself as I excused myself to refresh for a few minutes in private. When I returned to the living room, though, Daniel was standing over Lauren, who was seated in her favorite chair with her long legs turned to one side. The hem of her dress had lifted above her thighs, and the top was now beneath the swell of her compressed breasts. Daniel had one hand behind her head and was drawing her face closer to his waist, Lauren already sliding her fingers inside of his dress slacks after having unzipped them in my absence. I leaned against the doorframe as she handled his length, teasing the head with her lush pink lips. I hadn’t expected anything like the situation I found myself in, uncertain if I should retire to the bedroom myself or attempt to leave the apartment inconspicuously. Neither seemed a feasible option at the time, so I simply stood there and watched Lauren seduce her male friend by slowly sucking his enlarged cock in front of me.

I could feel my own clit begin to swell, just a touch of moisture beginning to saturate the lace panties which Lauren had chosen for me. She took her time pleasuring him, the sounds of her mouth sucking and slurping his cock making my knees close together to contain my own lust. Daniel shook as his knees began to buckle, then he was holding Lauren’s head firmly to push himself all the way inside her mouth. He kept her face close to his own body as Lauren shifted in her seat and began gagging to catch her breath. I could tell when he began climaxing because Lauren choked when attempting to swallow with his full length sliding down her slender throat. I didn’t know what to do, so I just stood there until he finished cumming inside of my own best friend and lover’s mouth.

When he pulled himself out of her, much of his orgasm flowed over Lauren’s lips and spilled between her cleavage. She used a finger to wipe the edges of her lips, careful not to smear her rich lipstick. She continued looking up into his eyes, even as her disheveled clothing continued to fall away for what would continue to happen that evening. Daniel had already noticed me standing in the doorway, motioning to Lauren that she should turn towards me and address our situation. She positioned herself comfortably with a pose that suggested her irresistible sexuality, then nodded with a subtle gesture that I should walk over to where she was waiting for me. Daniel took a step back, but didn’t attempt to conceal himself, despite the fact that his manhood was already firming up with an erection thick as my own slim wrist.

Lauren remained ever the distinguished lady, even with her breasts and thighs exposed, and her beautiful mouth moist with Daniel’s glossy cream. She took my hand and expressed how lovely I looked that night, encouraging me to turn slowly so that they both could see how much my image had changed since meeting Lauren only six months earlier. Daniel commented on my long legs and how the stockings and pumps made me every man’s deepest desire for a younger woman. His compliment made me blush, even as Lauren began to caress my thighs and began lifting the hem of my dress. She exposed the bands of my stockings, that often elusive and tantalizing border between a woman’s thighs and something even more enticing above.

Lauren positioned me to stand beside her, then motioned for me to sit with her on the cushioned chair. She caressed my hair behind my neck, giving me a soft kiss on my lips and breathing her warm fragrance across my face. I began to feel intoxicated by her nearness, Daniel only a handspan away with his cock standing straight up against his waist for me to see clearly. I closed my knees together, not sure where this was going or if I could even stand and leave if I tried to. Lauren placed an arm around my shoulders, then looked up at Daniel with a suggestive smile. I saw the exchange between them and felt a little panicked, but remained still as Daniel took a closing step towards us. His cock was throbbing hard with thick, colored veins along its length, and a full pink head which glistened from sliding inside of Lauren’s moist mouth.

I had nowhere to turn, so I watched Daniel approach with Lauren comforting me with soft whispers, confirming how desirable I was. Then I was making eye contact with the much older man standing over me, his hand sliding beneath my chin as he told me what a pretty girl I was and how he couldn’t take his eyes off of me all night during dinner. Daniel stood close enough that his head was right in front of my face, but it was Lauren who slid her fingers behind my neck to coerce my lips towards his luscious length of manhood. It felt as if my heart would explode when his head slid between my lips and over my tongue. I had only even given head to my first boyfriend, and he had been physically small and very gentle with me. This man was twice my own age and had an enormous cock pushed inside my mouth, while my own girlfriend sat beside me with her hand pushing my face towards him.

Daniel shuddered as his cock began to slide back and forth inside of me, every thrust making me gag as I attempted to gasp. Lauren simply sat there and continued to caress my breasts, lowering my top and fondling me as if we were all alone. I began choking as Daniel orgasmed down my throat, then managed a deep breath before he began to use my mouth once again. Lauren had my dress pulled up enough for her to lower my panties, which were now tangled around my thighs, nearly to my knees. She reached her fingers inside of me, making my clit and lips swell with every pulsation of Daniel’s mature member. I sucked him slowly at first, but he was intent on fucking my mouth, so I gave him the kind of head that I had only ever seen in porn videos before. I swallowed cum for my first time, gagging and choking as I sucked and slurped with my body being used between two older and much more experienced sexual partners.

Lauren was masturbating herself, even as she made me climax each time that I sucked Daniel off to cum. It felt like I had no sense of time that night. It might have been an hour or maybe two before Daniel stood back with his cock dripping onto Lauren’s hardwood floor, most of his thick load inside of my tummy, but some still drooling over my lips and chin and onto the dress, which was now saturated in cum. Lauren was still fingering herself as I lay back against the chair, physically drained and feeling sick to my stomach for all of the semen I had swallowed. Daniel looked pleased with himself and merely smiled before retiring to the bedroom, Lauren giving me a soft kiss on my cheek and then standing up herself. She finished undressing and began following him, then turned and told me to take my dress off but to leave the stockings on.

I had thought my ordeal over, but Daniel and Lauren were only beginning. I had nowhere else to go and would need a shower just to step out of her apartment, so I took off my ruined dress and smoothed my sheer stockings over my slender legs. The pumps were left aside on the floor with my panties draped over them, and then I was slowly making my way to yet another doorframe to watch as Daniel bent my girlfriend over the dresser and began to pump her hard from behind. I swallowed the sticky remnants of his cum inside my mouth and knew what they both had in store for me when he was finished with her. I stood aside, beside her bed, hoping that he wouldn’t use me so hard that it would hurt, but Lauren was already crying out, whether from pain or pleasure; I couldn’t be sure.

When Daniel stood back and left Lauren leaning forward in a slump of used feminine flesh, I knew that that night would change my life forever after. He turned towards me and told me to kneel on the bed, then closed the door as Lauren made her way to the bedside to watch how he intended to handle me. He was the first older man who Lauren invited into our bed, but he wouldn’t be the last. I think that she knew what would happen, even from that first time when she approached me in the record shop months prior. I knelt on her bed and felt Daniel behind me, his full girth pressed against my bottom, sliding between my cheeks, and then kissing my wet cunt with the promise of a long night ahead of me.

To be continued … soon.

Michelle

Published 2 hours ago

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