Evolving as a cuckold - through the seasons of life

[The Owl]

Scarlett and I enjoyed NRE as we explored each other's interests. She was comfortable being single. But she and I really enjoyed each other's company in and out of bed.

We hiked, dined, watched movies, read the same books, talked, and explored life together. I learned her history. She learned mine. I began understanding more about the nuances of her submissive nature. I learned that she fantasized about receiving a spanking, not a pretend one but one that may bring her close to tears. We experimented with OTK spankings, panties on... panties off. She did not want me to injure her or leave bruises. But she found some pain blended with her pleasure to be intoxicating. I was willing to accommodate her previously unexplored fantasies and desires.

To push the limits a bit further, I purchased some bondage cuffs. One evening when she was very aroused and we were both naked in bed, I slipped the cuffs around her wrists and ankles and began attaching the tethers to the bedposts. Scarlett didn't know I had purchased these cuffs and resisted at first. I reassured her that I would not hurt her and educated her how she could extract herself from the restraints if I were to fall over dead, or some other catastrophe left her stranded - tied to the bed.

She was sufficiently reassured to allow me to tie her arms and legs firmly to the bedposts. I used my hands to touch her body. I pinching her nipples between my thumb and forefinger, firmly enough to create momentary pain. I would quickly release the pressure and then used my tongue to replace the pain with pure pleasure - licking and sucking them, first one, then the other. Then, I got between her legs and teased her with my cock for a bit - edging her by running the tip over her clitoris time after time, carefully avoiding sufficient stimulation to cause her to have an orgasm. When I could fee her desire was burning hotter than a bonfire, I pushed inside her and fucked her without restraint while fully restrained. She exploded into one of her very powerful orgasms, but was unable to wrap her legs or arms around me while her body shook and convulsed.

After her release, I released her - unlaced her, allowing her to move freely within her state of bliss. We had broken through yet another internal boundary in our relationship - to each of our delight and pleasure.

As we cuddled in the bed enjoying the afterglow of our respective orgasms, Scarlett whispered in my ear - speaking softly in her irresistible Scottish accent, "I have an idea. We should find a handsome dominant man to join us. You can sit in that chair (pointing to a chair in the corner facing the bed) and watch him fuck me."

I was simultaneously aroused, startled, and somewhat anxious.

"What? Where did that idea come from?"

Scarlett replied, "You've told me about your past experiences and fantasies. I'm sure you would enjoy the experience." As I was processing what she had said, Scarlett moved her mouth closer to my ear and lightly sucked my lower earlobe, as if to punctuate her fantasy.

The seed was planted. Scarlett and I had read Esther Perel's book "Mating in Captivity." There is a chapter in the book titled "Inviting the Third."

Scarlett's statement began the creation of our shared fantasy of inviting the "Third" to savor the pleasures of Scarlett's pussy. When I was inside her and she was climbing the wall of arousal, I would sometimes stop, holding the tip of my cock between her labia but outside her vagina. Before nudging back inside I would whisper in her ear, "Do you want to feel the Third's cock inside you? Do you desire fresh cock?"

"Yes... I'm more than ready."

I pushed my cock back in... Scarlett gasped.. and soon her consciousness was shattered beyond thought as every nerve ending in her body savored orgasm. We continued to fuel the fantasy of the Third. We were in no rush, but we both were increasingly confident that we would like to explore the fantasy in 3D. If we did not like the experience, we agreed that we could make it a one-off experience. And, if we liked it, then we could add it to our repertoire of erotic experiences to enjoy.

We both enjoyed reading and writing. So, in addition to talking about this shared fantasy, we wrote erotic emails as well. Tumblr was replete with erotic photos at that time. We sometimes used one or more erotic photos as the basis for an erotic missive. More fuel for our shared fantasies. In our emails, we discussed whether a man in a photo was Scarlett's partner or the Third. If there were two men, which one was the partner and which was the Third? Was the picture taken pre-tryst, post-tryst, etc. Was the woman preparing for her erotic adventure with the Third or was she savoring the aftermath? If the picture showed a man and a woman having sex, was her partner present as an observer, or was she flying solo? If solo, was this a spontaneous tryst or was it planned with the full knowledge of her partner? What was the woman in the photo thinking and feeling? What was the man thinking and feeling? If there were two men, what were each of them thinking and feeling based on what was shown in the photo? What led up to the photo? What would happen next after the photo. All of these points of ambiguity were used to explore our erotic fantasies.

Want to hear more? Want to read one of the erotic missives I wrote for Scarlett before she actually cuckolded me?

[vicg]

Oh yes, definitely. This phase, where a couple is talking about it and working their way toward their first experience is super hot to me, and posters here rarely cover that in detail (especially when it was the woman who initiated the conversation).

[The Owl]

Oh yes, definitely. This phase, where a couple is talking about it and working their way toward their first experience is super hot to me, and posters here rarely cover that in detail (especially when it was the woman who initiated the conversation).

She initiated it... but she did so in context. She was confident that the idea would arouse me based on what she had learned about me during our discussions about the erotic. More to come...

[venus-can99]

Thanks for sharing the account of how you and Scarlett started exploring bdsm kinks leading in a way to imagining a third… imo most of readers would be game to hearing this next phase of your evolution…

[The Owl]

Thanks for sharing the account of how you and Scarlett started exploring bdsm kinks leading in a way to imagining a third… imo most of readers would be game to hearing this next phase of your evolution…

I shall continue. Thanks for the feedback.

[The Owl]

The follow is an erotic (fiction) story that I wrote to Scarlett in an email a couple months after she opened the door to the
Third. . The theme was sparked by a Tumblr photo of a woman in a very fancy library/reading room. She is on all fours on the plush carpeting, waiting for an erotic event, or so it would seem. Her skirt had been pulled up over her hips to her waist. Her naked ass was fully visible for all to see. And now to the email. The purpose of exchanging these fiction stories was to explore what we might enjoying doing il real life.
*****************************************
Scarlett was a natural submissive She desired submission. The fabric of Scarlett’s eroticism was knitted from the yarn of being soft and cooperative in the serve of the erotic.

This evening, Scarlett was preparing for an erotic surprise that had been arranged by The Owl. As commanded, after showering and primping, she donned the black silk dress that fit loosely below her waist. The top was supported by spaghetti straps allowing the delicate fabric to drape her unsupported youthful breasts. The Owl had instructed her to wear the matching high-heeled CFM shoes, her gold anklet – but nothing else – no bra, no panties, nothing but silk, high heels, and hotwife jewelry on her ankle.

The Owl had arranged a limousine to drive them to the edge of town where they would enter a gated driveway leading to a large well-maintained stone house – styled a bit like a medieval castle. The driver was quiet, handsome, trim, and dressed to perfection – consistent with Scarlett’s taste in men. She preferred well-dressed, dominant men. He was wearing a dark suit, a crisp white shirt, cufflinks, and a well-selected tie communicating confidence and a quiet, but commanding presence.
During the ride across town, the driver kept his hands on the wheel and his eyes focused on the road ahead. Now and then, Scarlett caught him glancing in the rearview mirror. On one such occasion, their eyes briefly met through the mirror. Scarlett enjoyed the brief eye contact with the driver, but no words were exchanged.
The Owl broke the silence in the back seat by whispering in Scarlett’s ear, “Move your hand under your skirt, touch yourself, and prepare your pussy for your surprise. Do not bring yourself to orgasm, but bring yourself close to the edge. Be discrete. The driver must not know what you are doing. No gasping, no moaning, no other expressions of pleasure.”
Scarlett fastidiously followed The Owl’s command, hoping that the movements of her hand would not be detected by the driver. The Owl watched Scarlett as she touched herself under the silk fabric. He smiled very slightly – a smile of approval in response to her compliance. Scarlett wondered if the driver had any idea what was happening between her legs.
When they arrived at the house, Scarlett was impressed with the exotic landscape and the mansion they were approaching. True to his training, the driver stepped out of the limo and opened Scarlett’s door. She accepted his offer of a hand to assist while exiting. As their hands met, Scarlett felt his strength and warmth as his hand cupped hers.
Then, she felt unexpectedly embarrassed knowing that the tip of her middle finger, now in contact with the driver’s upturned palm, had just been lightly touching her clitoris a few moments ago. As she stood up beside the car, a gentle breeze of fresh air wafted under the skirt of her dress. She could feel the breeze all the way up her legs – all the way to her wet naked pussy. She wondered if the air movement might be carrying the musky tang of her sex – from below her dress – from her fingers - to the nostrils of the driver or to anybody in the house. When fecund animals are in heat, potential mates detect pheromones miles away. The driver and The Owl were only inches away. She did not detect any posturing or flirtation from the driver or The Owl. But she was certain that sex was in the air.
The Owl led Scarlett to the front door on his arm. The driver told The Owl, “Take your time. I am in the middle of reading an excellent novel. Text me when you are ready to depart and I will bring the car around.” He slowly pulled away and headed toward a parking spot beyond the large outbuilding on the property.

The Owl behaved as if he knew the house. Without hesitation, he entered the front door without knocking. Classical music was playing on the sound system in the house. The music created an arousing backdrop, hitting just the right notes to help Scarlett feel centered. The Owl led Scarlett through the vestibule, down a large hall leading to the library. The room’s walls were lined with shelf after shelf of old books. The wooden floor was partially covered with a high quality Persian rug. The room was home to a variety of intriguing items – perhaps archelogical discoveries placed there by the owner - perched on the side tables. There were a few leather chairs in the room that looked as if they would be comfortable for reading or observing others.
Scarlett had a keen sense of smell. She detected a distinctively male musk in the room. A fascinating... arousing... erotic... aroma that she couldn’t place; it brought back adolescent memories – very private feelings harkening back to her youth in Scotland. She remembered being in a house not unlike this one when she was 16 years old. She was with an 18 year old athlete from school. His parents were gone for the evening. Scarlett accepted the glass of wine he offered. She was naïve. He knew exactly what to do. Scarlett discovered the pleasure of sex on a couch in that house. She wasn’t in love but she was curious about the forbidden, the unspoken. She did not resist when he slipped his hands under her blouse and deftly unsnapped her bra – with one hand. He disrobed her, then himself. Their maked bodies met in the dark, and Scarlett saw the light as he confidently but sensitively entered her.

The masculine smell in this library took her back to that experience – in her mind and in her gut. She felt the same feelings of anticipation that she had as a naïve teenage girl, who wanted seduction. The masculine aroma was comingled with the scent of leather – perhaps from the chairs.

The Owl broke her momentary spell when he commanded Scarlett to lower herself to her knees in the middle of the room on the carpet. Scarlett knelt. He then commanded her to lean forward and to support her torso with her forearms and elbows. “Place your hands flat on the carpet, where they will stay until I tell you to rise.” She followed his command as stated. Her torso was tilted down; her shoulders lower than her raised hips. Her spine was slightly swayed. She realized that The Owl had put her in mammalian lordosis – a submissive and sexually receptive posture.
Scarlett's long thick hair was hanging down the sides of her face obscuring her peripheral vision. She began to reach up with her left hand to tuck her hair behind her ear so she could see the door out of the corner of her eye. The Owl sternly told her, "Don't." She didn't. She put her hand back on the carpet as previously instructed.

The Owl reached down and slowly pulled up the hem of her silk dress - up and over her ass – fully exposing her naked hips. Standing beside her, The Owl used his hands to pull her butt cheeks apart far enough to inspect both orifices. The Owl dropped a hand down to her pussy and slipped a finger between her moist labia. She could see nothing but carpeting in the narrow field of vision between the cascade of hair falling beside her face. Her sense of hearing seemed enhanced by her arousal. “I know how much you like surprises, Scarlett. My finger tells me you are ready for your surprise. Are you?”
“Yes. I trust you completely. Please surprise me.”
Scarlett was submissively exposed from the waist down. Her head was close enough to the carpet to feel that it was woven from very high quality wool. The carpet felt good on her forearms and knees, and smelled as pleasant as a new cashmere sweater. There was no more talk. Scarlett felt pleasure as The Owl gently rubbed the curves of her buttocks, up to her waist and then back down to her upper thighs. He had dropped to one knee so he could reach under her, gently caressing her lower belly – slipping one hand over her pussy, the other roaming wherever he desired. The Owl’s confident hands caressed her while she maintained the submissive posture she had been commanded to assume. She felt reassured – and aroused - by his touch. She felt The Owl run a hand down her lower back, to the top of her crack, and then further toward the pucker of her anus, where his middle finger lingered. The Owl gently prodded slipping the very tip of his finger slightly inside this very private orifice. To date, her ass had been reserved exclusively for The Owl. He had taken her anal virginity about a couple of years ago. By mutual agreement, her ass remained his private sanctum since they had enjoyed that threshold experience together. Scarlett felt a frisson – a pre-orgasmic shudder of pleasure running up her spine as The Owl pulled back and stood up.

She dared not look but she could hear The Owl walking toward the door. He opened it. She heard two sets of footsteps walking from the door toward her. She could detect the noise that the sole of The Owl’s shoes made with each step on the wooden floor as he walked back toward the rug. The other steps coming from the door sounded like a man walking barefoot toward her. She could hear each step, but it wasn’t the sound of leather soles on wood. She reflexively began turning her head toward the door to see who was coming.. Before her head had moved even half an inch, the Owl firmly uttered, "Don't." She didn't.

Realizing that she had momentarily failed to be fully submissive, she knew that The Owl would punish her. She trusted The Owl and savored his punishments. With The Owl, Scarlett had learned the erotic pleasure that pain could bring her. Scarlett and The Owl had a safe word, but she had never needed to utter it, even when the pain was so intense that a few tears welled up in her eyes, a few sobs in her breath. The pain seemed to make her pleasure even more exquisite – like melted fudge dropped on ice cream – a delicious combination of hot and cold – the heat of pain, the sweetness of pleasure.
Standing beside her and without warning, The Owl’s familiar hand swatted her naked ass quite firmly. The sting caused Scarlett to gasp. She knew that another person was present in the room – standing behind her. She had heard his last footsteps directly behind her. He must be staring at her exposed ass as The Owl began spanking her. The Owl swatted her again, and then again. She felt the stinging pain of swats on her ass. She knew from experience that her buttocks were turning ruddy from The Owl’s repetitive swats on each ass cheek. Knowing that she was being erotically spanked in front of a stranger created a rarified blend of embarrassment and arousal. The Owl would not let anything harmful happen to her. But there she was, fully exposed... receiving an intense spanking... with a stranger in the room. She silently wondered about the identity of the stranger. But these thoughts were disrupted by yet another stinging swat as The Owl landed his firm hand one more time.
As quickly as the spanking had begun, it ended. Scarlett heard The Owl say, “Give her the pleasure she desires.”
Scarlett knew better than to look up again. She heard The Owl take a few steps away. Her ears told her that The Owl had seated himself in a leather chair a few feet away directly beside her. She heard other movement behind her. Although she couldn’t see anything, it sounded like the barefoot man was untying a knot in a fabric belt. She heard the sound of a robe dropping to the floor behind her. The momentary movement of air created by the falling robe felt soothing as it momentarily cooled her reddened ass. Scarlett was in complete suspense. Where was this surprise headed?

Scarlett detected the sound of the man kneeling behind her. She felt his thigh making contact with hers. The hair on his skin could be felt on the back of her thigh. At that moment of first contact, she could tell that his muscles were strong. She knew with certainty her surprise was masculine - a disrobed stranger was kneeling behind her while The Owl watched from his seat.
Scarlett felt more leg to leg contact as the stranger used his hand to guide the head of his erection, pressing it firmly against her swollen labia. She did not flinch, and kept her pelvis firmly in place, her back swayed, and her hands on the carpet. She expected penetration. She wanted penetration. Instead, he confidently used his hand to guide the tip of his cock up and down between her labia several times – moistening the tip and stimulating her clit. Near the top of each swipe – at the opening of her pussy, she wondered whether he was going to plunge himself into her. She made sure to brace herself with her upper arms each time his cock was in position. But each time, he slipped the head of his cock back down and ran it along the length of her wetness until it was touching her aroused clitoris where he would tease her with a few circular movements before moving his cock back up - torturing her with erotic anticipation.
After several rounds of this cock massage, Scarlett groaned – as if she was beckoning him to enter her. She was fully aroused. She felt as if she was only a few deep strokes away from bliss... away from release... away from petit mort.
The stranger placed one hand on the middle of her lower back and stroked her skin with his palm. His thumb found its way down her crack, fingers stretching up toward her back. She felt his thumb making small circles against her anus. He pushed firmly against the bud of her ass, but not firmly enough to penetrate. Scarlett liked the sensations she was feeling but also felt confused. The stranger was touching The Owl’s private sanctum in The Owl’s presence. Should she protest? Was The Owl putting her to the test? Was the stranger taking liberties with her beyond the limits set by The Owl when he was arranging this erotic surprise? He continued to push his thumb firmly on her ass, then lighter, then firmly again. Scarlett remained submissive as commanded by The Owl. He was in charge and if limits needed to be set, he would set them.
The stranger seemed to know that further ass play was verboten. He moved his thumb away from her ass, and used his other hand to bring his cock back up between her labia as he had done several times before. This time, he pushed firmly into Scarlett. His cock began sinking into her – deep inside her pussy. She was immediately pleased with his girth. It was large enough to impress her, but not so large to cause pain. Her pussy was nicely stretched around his cock, but his size did not impede penetration. The deeper he pushed, the fuller she felt. His cock continued descending into her very aroused pussy, inch by inch, until she felt the tip pushing against her cervix. His pelvis was firmly planted against her ass. He was in. His cock was long enough to create unique sensations deep inside her.
As he slowly pulled out, Scarlett savored the sensations created by his cock. It was long enough that he could thrust and parry several inches with each stroke, without any worry about popping out after one of his long slow withdrawals. Each time he slowly plunged back in and hit bottom, she felt increasing levels of arousal growing in her belly and chest. Her toes were tingling and curling inside her CFM shoes. Her breath was deepening and she could feel beads of sweat beginning to form in her armpits. She felt her body taking over, her pelvis naturally pushing back onto his cock with each plunge. The Owl was watching but all that was on Scarlett’s mind at this moment was the carnal pleasure of the fuck.
Scarlett did her best to savor being on the edge of orgasm for as long as possible. Eventually, the arousal overtook her. She gasped her way through an intense orgasm while her pussy spasmed around his cock. Her orgasm was lengthy and complete. As she was descending from the peak of pleasure, she felt the stranger picking up his pace. He grabbed her hips with both hands, and plunged his cock in and out with a new level of intensity as he approached orgasm. The only words she heard him utter throughout their tryst were, "Oh fuck..." while groaning through his orgasm. She could tell that all of his muscles were tense and was momentarily beyond consicious control as his cock squirted deep inside Scarlett. Through her submission to The Owl, she had tamed this stranger’s lust.

Scarlett felt completely sexually satisfied by the fuck she had just enjoyed. She felt certain that she had pleased The Owl by way of her submission to his command, submission to the third. The stranger withdrew his spent cock, and pulled his body back. She heard him stand up and don his robe. She could hear his footsteps as he exited the room. No words were spoken.
Scarlett remained in place as originally instructed. The angle of her torso was keeping the stranger’s semen deep inside her pussy, bathing her cervix in his fluids. She heard The Owl stand up and walk over to her. He reached down and lovingly touched her buttocks. He slipped a finger in Scarlett’s pussy, as if he was checking the oil in her engine. His touch, his probing finger felt kind and tender. The Owl lowered the hem of her dress over her ass and told her to rise. The Owl reached into his pocket and pulled out a pair of Scarlett’s panties.
“I brought these for you to wear home so you don’t make a mess of your dress or the seat in the limousine.”
“Thank you. When we get home, I will lay them out to dry and then tuck them away as a visual and olfactory souvenir that we can use to remind us about today’s surprise!”
After helping Scarlett slip into the panties, fully covering his well-used pussy, The Owl kissed her passionately and held her firmly in his arms. Scarlett felt reassured by his affection. Her enjoyment of the stranger had been vicariously enjoyed by The Owl. Her sexual transgression with the stranger, as commanded by The Owl, had brought them even closer as a couple.
Together, they walked back through the vestibule, out of the mansion, to the waiting car. The driver held the door for her. She saw his novel on the seat next to him. The bookmark had moved forward several pages. He looked exactly the same as when he had dropped them off. Was he the stranger who had fucked her? There was absolutely no hint that he was. Was there another man whom she had never seen who had given her so much pleasure with his cock? She realized that she may never know. She decided to savor the ambiguity rather than trying to nail down the details.
The ride home was quiet. Scarlett rested her head on The Owl’s shoulder, and rested her hand on his thigh. She felt satisfied and pleased with her surprise.

As they pulled into their driveway, Scarlett turned to The Owl and asked, "Did I please you?"

"Yes. Thank you. Before you bath, I want to taste your pussy. Will you allow me that pleasure?"

"The pleasure is all mine. And, I am happy to share the aftermath of my pleasure with you. Thank you for the surprise.”

[venus-can99]

Wow - what an erotic story Owl. Have you considered placing your erotic writings in the Library section?

[The Owl]

Wow - what an erotic story Owl. Have you considered placing your erotic writings in the Library section?

No... I haven't. My writing has involved telling the story of my last 40 years - hit and miss. Actually, I got laid the first time 55 years ago so it's even longer than I thought. The story I emailed to Scarlett (above) was fiction but is part of the factual story regarding how Scarlett and I moved further down the path of inviting the Third. It was written in the context of how we eroticized our relationship.

[venus-can99]

No... I haven't. My writing has involved telling the story of my last 40 years - hit and miss. Actually, I got laid the first time 55 years ago so it's even longer than I thought. The story I emailed to Scarlett (above) was fiction but is part of the factual story regarding how Scarlett and I moved further down the path of inviting the Third. It was written in the context of how we eroticized our relationship.

Perhaps you should if you have the time.Your style of writing is one of the best I have seen and mixed with your experiences and erotic letters to your lovers to draw upon IMO you have a lot of material.
Just a suggestion..

[shadowtantra]

Wonderfully written Owl. I completely agree with Venus

[The Owl]

Wonderfully written Owl. I completely agree with Venus

Thank you for the feedback Shadowtantra and Venus.

Question: What would be the advantage - if any - of posting my "evolving" story in The Library instead of here?

[The Owl]

Scarlett and I continued sharing more and more about our respective fantasies with each other face to face and in writing.

We learned more about what aroused her, what aroused me, and what aroused us as a couple.

After almost a year of talking, writing, and exploring, we decided to dip our toes in the water, rather than just talking about swimming.

We decided that we would visit a lifestyle club that we had read about. It was located in the Pacific NW.

We agreed that we wanted to meet other couples who enjoyed pushing boundaries. A lifestyle club sounded perfect We both agreed that we had no intention of being sexual with a Third at the club. But we also did not want to be too rigid or rule bound while planning.

In order to intensify our level of desire (perhaps to override the anxiety of actually going to a lifestyle club) we agreed to refrain from sex and orgasm for a week before our visit. We could flirt with each other. We could be naked together. But no sex, and no orgasm.

It was a long and challenging week. Each of us developed a fairly intense head of sexual steam before boarding our flight to the PNW.

Want a trip report?

[hornedhubby]

Please. Still reading and enjoying your story, Owl.

[venus-can99]

Thank you for the feedback Shadowtantra and Venus.

Question: What would be the advantage - if any - of posting my "evolving" story in The Library instead of here?

Speaking for myself- not suggesting that this wonderful thread be posted in the Library. My suggestion was for you to post some fictional stories like the letter to Scarlett….
IIRC a thread in Library lives for ever and is not subject to pruning.

[shadowtantra]

On the Library - What Venus says!

[The Owl]

Speaking for myself- not suggesting that this wonderful thread be posted in the Library. My suggestion was for you to post some fictional stories like the letter to Scarlett….
IIRC a thread in Library lives for ever and is not subject to pruning.

That makes sense.

[The Owl]

Our flight to the Pacific Northwest city where the club we had selected was located was uneventful. There was no turbulence but we both felt butterflies in our bellies throughout the flight.

We picked up our rental care and drove to the boutique hotel downtown where we had made reservations. The club was in a suburb that had begun as a separate town. The city and the town were now merged into one metropolis.

The first night in the hotel, we cuddled and kissed but we had both agreed to a week of no sex and no orgasm - mutual denial. So, we were cautious with our touching, knowing that we were both cocked and ready to fire.

We slept in the next day, ate brunch and had a leisurely afternoon. Our reservation at the club required us to show up at 6 pm for a newbie training session and tour led by a woman and man who were either employees or volunteers. We had been told that after the tour and class, the club would open at 7 pm for members who had made reservations for that night. A buffet dinner would be served around 7:30 pm. Then the party would begin with dancing on the first floor and partying upstairs. There was a locker room near the top of the stairs. Before walking much further around the second floor, and before even thinking about ascending to the Third floor (...the floor where Scarlett might meet her Third... skin to skin), you had to be undressed. Lingerie, panties, and bra (or men's boxer shorts) were acceptable. But you were not allowed to make people upstairs uncomfortable by showing up with your clothes on - to gawk.

As the afternoon wore on, Scarlett and I were becoming increasingly anxious about the impending evening. Were we really going to go to a club where people would be having sex with others - people other than their partners - in an open room? Would a woman approach me for sex? Would a man approach Scarlett for sex? Would a couple approach us as a couple - for sex? We had read and fantasized a lot, but this was the real deal. How would we feel? How would we respond?

We didn't want to put too many rules on the evening but we also did not want to dive into extremely deep water only to learn that one or both of us didn't feel comfortable swimming.

The club was ranked as one of the best swingers clubs in the country. It was one of the first clubs to be extremely focused on making women feel safe. The club prided itself on being focused on women's pleasure. If a woman said "No", it meant "No." No questions asked. The club catered primarily to couples but single women were welcome to attend. The club had a few select males that could come solo but those "solo male" tickets were extremely rare and were coveted by the men who enjoyed the privilege of attending without a female partner. When going up the stairs to the play areas, a man could not go up solo. But a woman could take as many men as she wished, as long as those men stayed with her upstairs. The club did not want random men roaming around upstairs without female supervision, so to speak. The club had a reputation of being focused on women and their desires.

The general rules that Scarlett and I had agreed to before going to the club that night were that either of us had the right to use our safeword. If one of us uttered it, we would both retreat, and - if necessary - leave for the hotel together. Another rule was that we were open to "softswap" but we would not jump into intercourse with another person during our first visit to the club. Softswap could include erotic dancing, kissing, petting, but not intercourse. Scarlett was open to me flirting with other women and I was open to Scarlett having some erotic interactions with a man (or a woman... but Scarlett was not very attracted to females and an erotic encounter with a man was central to her fantasies).

However, I didn't want us to structure the evening too tightly or to be constrained by too many rules. So, I told Scarlett, "If you want to have sex with somebody at the club, tell me. If I'm comfortable with that idea, I'll let you know. Let's play this evening by ear."

Scarlett replied, "Ok. But I doubt that will happen during our first visit."

Now we weren't just talking about visiting the club, we were on the brink of doing so.

After we had both showered at the hotel and before we began donning our club clothes, I pushed Scarlett's freshly washed body onto the bed and climbed on top of her - belly to belly - breast to chest. I began kissing her intensely. She responded with fervor. My cock was fully erect and the head was positioned at her labia. I instinctively moved my pelvis and nudged up even closer and tighter. We both felt the tip of my cock beginning to push up and into the port of entry to her pussy. About half of the head of my cock was inside her portal

Our lips pulled apart, my head rose, and I looked into her eyes. As a natural submissive, Scarlett would have allowed me to take my pleasure in her pussy without resistance. But we also both knew that if we made love, our respective desire to go to the club could wane. I pulled back further and said, "Let's get dressed for the club."

Scarlett smiled and said, "Wow... that was close."

As she rose off the bed, she said, "I was looking for my razor. I want to run it over my pussy one more time before I put on my thong. I don't want anybody feeling stubble." She nervously giggled and then said, "I feel like I'm back in college getting ready for a date! I not only want to smell good, I want my pussy to feel smooth as a baby's butt. I want to be ready for anything that might happen on this date. I'm feeling as frisky as a coed. Take me to the party!"

She knew how to arouse me with her words, spoken in her highly erotic Scottish accent.

We dressed and drove to the club. We arrived about ten minutes early. I was so nervous that I drove around the block a couple of times before driving onto the premises. Scarlett was quite nervous too. But we were determined to push through our anxiety, and to attend the required orientation class and tour with the other newbies.

Want to hear how the evening unfolded from there?

[venus-can99]

What a fantastic setup for your activities at the Club. Would love to hear how the evening unfolded

[shadowtantra]

Waiting for more Owl!

[The Owl]

Orientation at an upscale swingers sex club was quite an experience.

A couple guided us through the club explaining the does and the don'ts.

They toId us it's all about the women's pleasure.

When a woman says "No", it means no... not maybe, etc.

The guy who checked our IDs to see if it matched our reservations turned out to be quite nice and supportive. Anxiety went down a bit.

There were about five couples and one single woman in the orientation. We were all newbies and were all somewhat anxious.

The single woman was about 40 yo. She looked professional, healthy, and engaging. I think she felt odd being there alone when everybody else was coupled. At one point, we were in a room full of bunk beds and mattresses. The single woman leaned against the wall while we were listening to the couple giving us information about this and that. She didn't realize she was leaning against the light switch. The room went pitch black. None of us, including her had any idea why the room was dark. One of the guides figured out where the switch was, reached behind her and turned it on. She was embarrassed about putting us all in the dark. We thought it was funny. The lights went down. Were we suppose to start having sex with each other? She didn't think it was so funny. I think accidentally turning off the lights increased her anxiety. She looked like she wondered what she had gotten herself into.

The orientation was over. We either had to pay the entry for the night or call it a night. Everybody in our group of newbies stayed except her. I thought about reaching out to her and encouraging her to hang with Scarlett and me. We could be her anchor at the evening of debauchery!!! But I thought Scarlett may not take kindly to me flirting with another woman by way of asking her to stay with us for the evening at the sex club. So, she quietly departed never to be seen again. I wondered if she ever came back and gave it another whirl.

Scarlett and I stayed. We had brought a bottle of wine with us and drank a glass to settle our nerves. Regulars were floating in for the evening. We chatted with several interesting people before the party began. One was a 30 yo woman from New Zealand. Her husband was about 70 yo. She introduced me to him as her husband. He then left. The club was her place to get her sexual needs met. Her husband and she seemed quite loving to one another but she wanted some young hot blooded male to bed her at the club. Her husband was either neutral about it or enjoyed her cuckolding him at the club.

The evening began with dinner... so Scarlett and I filled our plates and set down with about three other couples (8 people at the table).

To be continued... Too tired to write more.

[guitarman]

Owl, As always, your recounting of these events is compelling. I'm sure I speak for many of us wannabees who have never been to a sex club what recollections you had from your first time. Looking forward to your continuation of this story.

[The Owl]

Before dinner, while everybody was milling around and some music was playing, a couple approached us. They figured out we were newbies. The husband was well nourished (...big belly but not morbidly obese) and the wife was not really my type either. I think they thought they had found playmates but after we filled our plates at the buffet, Scarlett and I headed to the table mentioned previously. Six of the eight seats were occupied by three couples. We three the other couple off our scent easily.

I don't think anybody at our table believed we were newbies and naive to being at a sex club. The handsome guy seated next to Scarlett had been there a lot of times and said, "Let's not pretend we're naive." The fact is, Scarlett and I were.

I enjoyed all of the sights. There was a live band and lots of dancing - one FMF threesome that danced in synchrony as a trio. The spirit at the club was lighthearted, playful and fun.

Eventually, Scarlett and I decided to go upstairs. The rule was you couldn't go to the sex floor dressed. You could wear underwear or lingerie but no clothes covering most of your body. That might make naked people feel uncomfortable. We put our clothes in a locker and ascended the stairs that we have visited during the orientation tour.

There were already quite a few people upstairs who were naked and enjoying sex. There were bowls of condoms everywhere. The area felt safe, clean and inviting.

Scarlett and I found an elevated bunk that was not occupied. We could see and hear everything from there, and could enjoy ourselves as well.

Another couple was in a bunk a few feet away. I found myself looking at her and she gazed at me. I considered asking them if they wanted to swap partners with us but that might have been too far for us to push it during our first visit. We had agreed that we would limit ourselves to "soft swap" during the first visit - no intercourse with others that night. We had both made it clear that we were open to revisiting that rule as the night progressed but we wanted to test the waters before jumping in head first.

Watching that couple make love was very erotic. There were others farther away making love too. Scarlett and I began enjoying sex. Scarlett can be vocal during sex. As she began moaning with pleasure, the room grew louder and louder as other women moaning too. It felt like the room became a chorus of female pleasure.

In nature, I think one of the functions of female moans of pleasure during sex is to arouse other males in the vicinity. Sperm competition is real. Women are not monogamous by nature. Arousing other males in the vicinity is a way to maximize the likelihood that an alpha male will deposit his semen in the moaning woman, optimizing the likelihood that her baby will be vigorous. Sex in nature also serves a social purpose (think bonobos) but at the end of the day, keeping the genes in the gene pool is the ultimate purpose of sex. We're all a product of a sperm in male semen fertilizing a female egg.

After Scarlett was done praying ("Oh God... Oh God... Fuck... Oh God...") during her orgasm, I drove my semen home as I grunted my way through a subsequent orgasm. I had been clipped earlier in my adulthood and was shooting with blanks. Given that I was having sex with Scarlett, no condom required. No glove... and lots off skin on skin love.

As we savored post-orgasmic bliss, we watched a very attractive young woman leading a handsome young man by the hand toward another bunk close by. They climbed onto the bunk and began arousing each other with kisses and caresses. It was fairly obvious that they were not familiar lovers. At one point, she stopped him and said, "Do me from behind..." He looked slightly perplexed. But she rolled over and got on all fours. It didn't take him long to figure out what she wanted. He got behind her on his knees and entered her. She moaned and pushed back as he pushed in. She lowered herself on her chest with her ass elevated. He had stamina and kept fucking her until she shook with an intense orgasm. It looked like she continued to have smaller orgasms as he continued giving her pleasure from behind.

Finally, he came and pulled out. The tip of his condom bulged with his semen. I watched him roll it off and use some tissues next to the bunk to clean up. She turned to him and said, "Thank you... I enjoyed that." He smiled and said, "My pleasure." They climbed back down and headed toward the stairs, probably to find each of their partners with whom they had come to the club.

The entire evening was very arousing. I didn't need any more sex but enjoyed the sights and sounds of sex. I told Scarlett that I was fine and that if she wanted to seduce any of the men at the club, I was fine with her going for it.

She told me she had enjoyed the evening and that we should head back to our hotel. In the locker room, we were almost dressed when the well-nourished guy spotted us. I think his wife was upstairs enjoying sex. He was in his boxers, shirtless looking a bit tubby. Scarlett did not find him attractive. However, when he said, "Would it be too much to ask you to show me your tits?" Scarlett boldly pulled up her top. She was not wearing a bra. Her perfect breasts were his to savor for a moment. He said, "Thank you." And we were off.

That first visit was a great introduction to how comfortable being at a sex club could be. The guy who had checked us in, saw us heading out and came over and gave Scarlett and me a hug. He said, "I hope you enjoyed yourselves." Scarlett replied, "We did." That night gave us a LOT of erotic energy to enjoy when we were back home - life as normal... but now we were no longer sex club virgins.

[ALLMYEXES]

I'm just now reading your story. I'm on Sat Jul 13, 2024 3:12 pm and read your comment "45 years later, S and I began communicating again through the internet. She told me things that I never knew that helped it all make sense."

I am about 1 year older than you so I can also say "45 years ago" and think back to a lifetime of experiences and some conversations that explained everything 25 to 50 years later. Sometimes decades go by and then one chat on Messenger out of the blue and things click and the pieces all fit together.

[The Owl]

I'm just now reading your story. I'm on Sat Jul 13, 2024 3:12 pm and read your comment "45 years later, S and I began communicating again through the internet. She told me things that I never knew that helped it all make sense."

I am about 1 year older than you so I can also say "45 years ago" and think back to a lifetime of experiences and some conversations that explained everything 25 to 50 years later. Sometimes decades go by and then one chat on Messenger out of the blue and things click and the pieces all fit together.

So true. Some pieces never fit together. But when they do, it's so interesting... and sometimes relieving.

[Rogueuser1]

What a great story - that is kind of funny that the guy with stamina seemed confused about doggy style... I wonder what his backstory was! At least he gave her a good time though!