This is based on a true story as related to me. Events and descriptions have been altered for storytelling purposes and, of course, the names have been changed.
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I will never forget my first contact with Ryan.
"I am a discrete, professional, single male. I will awaken you sexually…expose you to a sensual world of eroticism all around you. Meet me…and change your life. I am genuine and will not disappoint. Only your prompt reply will convince me of your interest and sincerity," the message glared on the computer screen.
He had answered my ad in an on-line swinger's dating service. I suppose it was a same mix of curiosity and desperation that had me sign up in the first place that made me reply back to the mysterious message. My ad had lingered for months attracting many inquiries, from couples, single men, and single women. I checked it daily and I was typically nonchalant about answering. But Ryan's message definitely caught my attention.
We traded messages over the next week, mine flirtatious, his assertive and confident. I started out coy, but was dying to meet him at the end. Finally, we agreed to meet at a local restaurant the next Friday night, for dinner only. I spent the next week in a funk of anxiety and anticipation. It was like I was a child again, looking forward to some big event, while time seemed to pass slower and slower, as the event grew near. I was determined to look good, dress conservative yet mildly seductive. I wanted, needed, to make a good impression with Ryan and not especially for him, but for me.
I live in a small town where I had moved when I married my first love. My husband and I were employed as professionals, enjoyed lucrative careers, and had started a family, I had given birth to a son. However, over time and for a number of reasons, my husband and I began to grow apart. Our relationship became empty, lifeless, and while I remained faithful to him, he finally admitted he was having an affair and wanted out. Suddenly I was on my own, filing for divorce, coping with a disconcerting emptiness, and scrambling for answers to questions I thought only other people had to contend with.
My son became the focus of my life. My ex and I agreed to share custody. While opportunities to meet new prospective partners were few in the immediate area I knew I could not bring myself to leave my only child. I had to stay, I had to make the best of it. Conscious of my divorce, my professional status, and being in a small town, I maintained a very proper lady like demeanor. I did not want my son, my employer, or my husband's family, hearing gossip. Recreational activities, my career, travel, and being a parent were fulfilling my life. My lack of sexual activity was of little concern. I had suppressed myself sexually through the almost two years of separation and divorce, and for some time previous. I had somehow denied it, but as our marriage broke down, the sexual gratification from my husband was on a similar, steady decline.
However, as time passed and I adjusted to my new life, I felt a sexual hunger returning. I began to look at the men I would meet differently, and while maintaining my lady like façade as a happy and content divorcee, began to secretly long for companionship and sex. I didn't act on these feelings immediately, I wanted desperately to remain discrete, which was one of the motivators for me to check out alternative ways to meet men, and to a lesser extent women. I cannot say I am truly bisexual, but could envision myself trying at least some soft play with another of my sex.
Medium height at 5'6" I had an athletic build for a woman which I worked hard to keep in top form. Golden blonde hair and blue eyes on a finely featured symmetrical face I had always felt confident, if not just a little sexy, with my look. My breasts were large and firm, a size 36C, with rose colored aureola and plump nipples. My thighs and legs were long and muscular converging on a neatly trimmed pussy with a long slender slit of my womanhood. In my mid-thirties I kept my weight under control, in fact, due to the stress I had been through I was actually lighter and slimmer than I had been ten years ago.
Among my many pastimes I am a voracious reader. As my sexual appetite increased I found myself seeking more and more material on sex, particularly from a social perspective. Which is where I discovered the 'lifestyle' or 'swinging' as it is more popularly known. As baby boomers age into their forties and fifties their impact on the 'lifestyle' has been as dramatic as it has been to other areas of the economy. Facilities, organization, rules, and even social acceptability have improved. While truly for couples, single women were welcomed, and I read that for many women it was a discrete and safe diversion from the bar scene. Wanting to avoid the latter it caught my interest.
It was my curiosity about the 'lifestyle' that led me to find where local swing clubs were located and find an on-line swinger's dating service site on the net. I went back to it a few times before actually logging on and creating an identity. Feeling just a bit excited and embarrassed, I filled out a few of the basic questions ignoring more detailed information requested. The thought 'I can't believe I'm doing this' crossed my mind more than once. I had no way of knowing where any of this would lead.
The responses I got were, to say the least, interesting. Ryan didn't come along at first, and if he had, I probably would not have responded with any encouragement. I was close, but not yet ready to begin seeing someone again. I corresponded with couples, and a few men and women that seemed intelligent and interesting. I enjoyed the attention and soon found going to the site to pick up mail was a daily ritual. I was still somewhat inhibited, and although a genuine interest in men and women had definitely returned to me, I needed something to get over that last bit of apprehension. And that's when Ryan's message flashed on my computer screen.
Our first date was at a nice restaurant, his suggestion, and to be dinner only although I think we both knew it could lead to more if impressions were favorable. I found Ryan to be very attractive. He was tall and lean, just over 6', very well dressed and, although almost ten years my senior, in great physical shape. He was polite, courteous, a real gentleman. He complimented my looks, my perfume, my clothes, and laughed easily at my offbeat humor. I thoroughly enjoyed his company, I had not realized how much I missed the companionship of a man, and it felt good.
We ate, drank, and talked for what seemed to be hours. Ryan listened to me intently as I told him things I never thought capable of. The swinger's forum where we met opened up intimate things about one's fantasies and inner most desires that one rarely will share. I had so many things I wanted to experience, and hadn't. Ryan showed little emotion through it all. Finally, when I asked him to share one of his fantasies Ryan told me that he, and some of his friends, had been participating in 'the lifestyle'. Perhaps it was the wine, my mood, the situation, or maybe simply that I knew he was interested, I found myself expressing an interest in 'lifestyle' activities, if in fact, we got to know one another better.
By the end of the evening all the talk of sex, my fantasies, and his mere presence had me very aroused. I decided I wanted to seduce him but the more I made advances, the more he seemed to retreat. Ryan plays the game of seduction better than anyone I know. And the disinterest he conveyed, by his lack of response to my behavior, only served to make me want him more. I sensed he knew perfectly well all along I wanted him, but decided to enjoy my pursuit. It bothered me but I realized I was the overanxious one looking for a conquest. Ryan stayed cool throughout. He walked me to my car after dinner, gave me a light kiss good bye and began to walk to his car.
"Ryan…" I heard myself saying. "Why don't you follow me to my place…we can have a night cap…my son is at his father's."
He nodded, accepting with a smile. "Drive carefully," he called out as he got in his car. At the house we continued to talk. Turns out he liked single malt scotch whisky which fortunately I had in the house, for the odd time when my father visits. I handed him the scotch and sat beside him on the sofa. I deliberately placed my hand on his thigh and rubbed it toward the inside. He didn't flinch, instead looked at me intently, peering deep into my eyes. He casually brought his arm over my shoulder but went no further. The silence was deafening as I looked at him, my eyes pleading to be kissed. 'Did he want me to beg him for it…surely he could see I wanted him,' I thought.
"Ryan…do you find me…attractive?" I stumbled over the words such was the state of my insecurity at the moment.
"Of course Andrea, you are a very sexy woman," he said soothingly and leaned forward to kiss me. A soft moan escaped from me as he said it. My body tingled with raw desire as our lips lingered together. He drew back, then forward again, I felt my mouth opening, his tongue moving deliberately forward. We kissed long and hard, I grew wetter by the moment. His hand moved off the top of the couch and caressed my hair, I loved that and wondered how he knew.
Our kisses grew more passionate and soon my make up was smeared about my face. I didn't care, I loved it, lost in the moment. It felt liberating, it had been…too long. His other hand was on my thigh, rubbing gently, I could feel the sensation through my silk stockings. I shuddered slightly as his hand shifted down to the sensitive area behind my knee and stroked it lightly with the tips of his fingers. He seemed to know all the right spots to caress and stimulate me.
"Andrea, do you want me to stay with you tonight?" Ryan whispered in my ear.
I didn't answer but my eyes betrayed my desire. He nodded slowly. "Take off your clothes for me…slowly…that's it… seductively…sensuously," he murmured as I began unbuttoning my blouse.
Ryan watched me intently. When I reached the last button I stood, then let my blouse slip to the floor behind me. My skirt was next leaving me in a fine lace bra, panty, and garter belt set. Being well dressed, for all occasions, was a minor fetish of mine. I moved to unhook one of the garters when he interrupted me.
"Not here," he said. I looked at him quizzically.
"Somewhere more comfortable?" He nodded approval.
He stood, took me in his arms, and kissed me again. His hands deftly unhooked my bra and I felt it fall away as he took a step back. My breasts felt the coolness of the air and my aureola crinkled as my nipples grew hard and taut. I felt the air escaping my lungs in a huge sigh as I experienced the first strong adrenaline rush of excitement. It had been so long since I had been laid, and here I was with this tall, handsome guy. I imagined him in me, on me, with me…it was exhilarating.
"Lead me to where you want me to make love to you," he said softly. I willingly complied leading him into the back of the house. I was taking him into the guest bedroom but as we passed the door to my bedroom Ryan stopped. "Your room?" he questioned.
"Yes," I replied.
"In there then, I will take you in there," he said decisively. I hesitated but then quickly led him inside, I wanted him, and I didn't care where.
Once inside he had me lay on my bed and then, as I watched, playfully undressed. He too was fastidious about his clothes as he carefully folded or laid everything he took off over the dressing table chair. Ryan was soon naked, my eyes were drawn to his long slender cock, not yet fully erect. It had been awhile since I had had one of those to play with. He noticed me staring.
"Andrea, do you know how to satisfy a man orally?" he asked.
"Yes," I managed to say, for a moment catching myself as slightly embarrassed.
"Good, I enjoy oral sex. Pleasure me, won't you?" he asked while moving over to my side. I took his cock in my hand and felt it swell as I stroked it. I ran my tongue from the base to the tip of his cock, lingering on the sensitive underside of the head. I could hear him exhale, almost a sigh, as I worked my magic. "Ahhh…that feels good Andrea…suck on it, make love to it," he instructed, clearly enjoying my technique. I did as he asked. I had always enjoyed giving head and soon took Ryan's full length into my mouth down into the opening of my throat. I could feel the blood pulsing in the veins of his shaft as I sucked him in a slow deliberate fashion.
I worked on Ryan for some time until my lips, tongue, and cheeks felt like they were going to burst. "I'm sorry Ryan," I panted slightly as I withdrew from him. "It's been a while since I've done this."
"Time for me to return the favor," he said understandingly. I was relieved he seemed unconcerned. Ryan stretched out his hand to me, helping me up. He kissed me lightly, his tongue gently chasing mine. I sat down on the edge of the bed and Ryan gently rolled me onto my back. As Ryan carefully and deliberately removed my stockings, garter belt, and panties I began to tremble with excitement at the touch of his hands.
"Neatly trimmed I see…I like that," he said as he lightly tugged my panties off my hips. He looked at me approvingly. "A little wet also…you're ready for me aren't you?" The wild look in my eyes could have only given him a resounding yes. "I want to taste you…" a moan escaped me as he said it, I knew if he just touched me I would cum almost immediately. "But can you touch yourself for me first Andrea? I'd like to see you touch yourself." Slight embarrassment passed quickly, I would have done anything he asked.
I spread my legs open for him and fingered my pussy as he watched. The long slippery slit of my womanhood filled with my juices, a reflecting pool of passion. I smiled wickedly at him as I drew my finger to my mouth and playfully licked off my own juices. Ryan smiled broadly. "Yes, like that Andrea, just like that…" then bent over top of me to suck on my engorged nipples. He flicked them gently then slowly drew one, then the other, into his mouth, teasing with his tongue as he drew in my flesh. It produced a wonderful current of sensation from my breasts to my pussy. A deep moan escaped as I exhaled. He kept up his tongue action for a few minutes then began caressing my thighs with his soft hands.
His touch was like silk running over my body. I know of no other man with hands so gentle. My thighs opened up even further for him letting him move down to the crease joining my thigh and pelvis. I noticed my breathing growing heavier, more urgent as he continued to suck my nipples. He hadn't even touched me 'there' yet and I felt I was going to cum. Sensing my condition Ryan stopped his sucking, his tongue laving down the undersides of my breasts, kissing them lightly. I raised my head off the bed and gave him a look of protest.
Smiling as he saw the distress on my face he said, "give yourself to me Andrea, relax." As I heard his words I was fighting back the rising orgasm within me, I didn't want to come yet, or at least I didn't think I did. Ryan suddenly moved back to my nipples, sucking one of them hard, while his hand moved up to the other, pinching and rolling it with his fingers. I cried out as he did it as the intense sensation drove me over the top. My hips bucked off the bed as I came, an agonized "Ohhhhh…" escaping my lips.
I could see lights flashing in front of me as a sharp, intense orgasm rushed through me. I felt the gush of warm fluids between my thighs, my pussy swollen and drenched. Ryan held me close as I quivered involuntarily, his strong arms, his body, and his scent comforted me. It was somewhere I had not been in a long while, and had not realized how much I missed. The soft hands continued to rove over my body, searching out places I had not thought erogenous, that is, until now.
"That…was great," I whispered gratefully.
"That…was nothing," he replied. "Do as I ask and there will be more, much more. Andrea, you are at the peak of your womanhood, you simply don't realize it…and have not had a partner who will help you explore it."
I looked at him for a moment. He seemed so confident, self-assured, a gentleman, someone I was 'safe' with, that I could trust. I could feel myself getting aroused again as he caressed me. Maybe this was what I longed for. A man who could help me both discover and explore a side of me I knew existed, but had suppressed. I knew I enjoyed his company, I was attracted to him sexually, what did I have to lose by letting myself succumb to my own fantasies?
Ryan was unhurried as he asked, "Will you let me taste you now?" Normally I would have been too sensitive after an orgasm but, other than my light fingering, my pussy had received little direct stimulation. I was ready and nodded my agreement. He sat me upright and moved behind me, pulling me to him so my back was leaning into him. In slow circular motions he swirled his tongue sensuously around the base of my neck and shoulders while his hands reached around to seductively squeeze and play with my swollen and sensitive breasts. My breathing became short and choppy as my excitement and arousal rose quickly. I knew he would go down on me and somehow I knew he would be expert at it.
Gently lowering me to my back as he swung around in front of me Ryan positioned between my legs. He looked up at me, our eyes locking for a moment, before he lowered his head to taste me for the first time. Using his long slender tongue he carefully traced along the entire length of my slit, my juices oozing out even under his gentle pressure. Sliding his tongue between my outer labia I knew he could taste the tart flavor of my inner lips and core. He carefully avoided my clit, a small but distinctive bud typically well hidden within its sheath. I felt his hands underneath me, carefully lifting me up so that he had better access to my pussy.
I could feel the softness of his tongue, the delicate yet provocative probing, sending warmth, tingles, and electric sensations throughout my body. 'This guy is great,' I thought as I enjoyed his attention. Ryan continued to work his tongue in and out of my pussy, lightly sucking on my inner lips until they protruded out of my slit. I moaned at his every touch as he alternated between the flat, soft surface of his tongue to lick and lave, and the harder point of his tongue to probe and stimulate. My juices flowed unabated, the moisture perceptible on my thighs like a thin sheen over my smooth skin. Ryan never seemed to tire and I could have let him go on all night. I could not remember oral sex ever being this good before. I felt him slowly get closer to my clit, by now fully engorged. "Suck my clit Ryan…god, please suck on it…make me cum for you," I implored him as I moaned and whimpered. I noticed his eyes transfixed on my face, as if enjoying every contortion of pleasure it showed…pleasure only he could bestow.
It seemed forever but, in reality, it was probably only a few minutes later when he turned his attention to my clit. I gasped as he spit on it then gently rubbed his finger around it driving me to the edge. In one motion he lowered his head and, using his tongue rapidly flicked it across my clit several times. My body stiffened and I clutched the bed spread in a death grip as an orgasm, much stronger than before, surged over me. I screamed involuntarily as Ryan then took my clit in his lips and sucked it like a tiny cock. My hips bucked wildly off the bed as this orgasm came in waves, each one stronger and deeper than the one before. I could feel the veins popping out of my neck as my entire body pulsed with the incredible sensation.
"No…no more…please Ryan," I weakly gasped as I almost fainted. I remember him lightly licking me before raising his head to look at me. I must have been quite a sight. Out of breath, completely taken over by pleasure, I lay there before him completely spent. It was absolutely the best orgasm I had ever had in my life.