“One of the boys from the Gym is training to be a masseur, he has offered you a free massage,” I told my lady Sarah. “Some of the boys speak highly of him.”
“A massage while naked I assume?,” she asked, her interest piqued immediately.
“You know I would love to watch his hands massaging all over your naked body.”
“Does he have any experience with females?”
“Let’s find out.”
Sarah is always looking for new and exciting ways to have her body sexually pleasured. A massage while naked from a trainee masseur, just half her age while I watched had the promise to be very exciting for both of us.
We were watching some video clips of young, male masseurs massaging naked, older cougar women, when I told her, “The thought of a man their age massaging your naked body while I watch is an exciting thought Sarah. What if the masseur wanted to penetrate you with his finger while me was massaging you? How would you respond?”
“You know me well enough to know it would be tempting for me, very tempting, especially if he had big, thick fingers to penetrate me.”
By chance, or was it serendipity, we ran into the boy Brian at a social function. Confirming for Brian, my lady Sarah was a demure class act, so sophisticated with her honey blond, bobbed hairdo, so elegant in her designer outfit. Flirting with him to show she was an incredibly classy, confident, elegant and sexually sophisticated woman.
He couldn’t keep his eyes off Sarah, undressing her with his eyes. Sarah was flirting with him, she had lots of questions for him while she looked at his big thick fingers.
His interest increasing when Sarah asked, “Do you realise I am French, that I am bi-lingual? Roger told me you want to practice your massage skills on me. He told me the boys at the gym speak highly of you. Do you have any experience with women? Older women my age, women twice your age? Massaging cougar women while their men watch?”
“I have massaged women while their men watched. You will be the oldest woman I have massaged Sarah. And already the most exciting while your man watches.”
Confirming he had offered Sarah a free massage as part of his training regime.
“While I am naked I assume?,” she asked flirtatiously, confirming her interest in receiving a massage from the boy. Her playful sexual attraction to the young boy obvious to others nearby.
“While I massage your naked body Sarah it will be important to let go of your expectations. The goal is simply to become more aware of your body and remain comfortable throughout the experience.”
“I expect you to behave professionally while you massage my naked body. Will you be professional for me? Do you promise you won’t try to seduce me while I am naked?,” Sarah taunted.
A few days later at three in the afternoon Brian was topless in tight, white shorts and sneakers after setting up his massage table. He was a good looking twenty-five year old boy, twenty-years younger than us, with a toned six-pack body.
A few minutes later he met Sarah for the second time, her cheeks flushed, excited at the thought of a new, much younger man massaging her naked body with his hands and big thick fingers. She was wearing heels and was obviously naked under her short, black silk dressing gown.
“Is this going to be a professional massage? Or a massage as sexual teasing, sexual foreplay?,” Sarah asked as she noticed the dim the lights and burning incense to set the mood for her massage.
My voyeuristic side was anticipating watching his hands on my lady’s naked body. Will she enjoy it? Where might it lead to? Will it be just a professional massage or will it lead to sexual teasing? Will he be able to resist the temptation of Sarah’s naked body? Will he try to seduce her? Will I be comfortable watching a new man with his hands on my lady’s naked body? Will I have an erection while I watch? What if he wants to have sex with Sarah? What if he tempts Sarah with his hands and fingers on her naked body and she wants to receive sexual pleasure from him?
“I am ready for you. You still haven’t told me if you have any experience with women? Older women my age Brian?,” Sarah asked again. “Let’s find out,” she smiled as she slowly opened her gown to tease Brian with her naked body before she let her gown fall to the floor, her exhibitionist streak in full play, completely naked for the massage boy and me.
Just as I wanted, he was admiring Sarah’s naked body, her freshly trimmed honey blond pubic hair, just a tuft above the meeting of her thighs, as he picked up a bottle of oil, and filled his hands with oil.
“Can I leave my heels on?,” she teased some more, full of confidence as Brian ogled her magnificent naked body as he helped her lay face down on the massage table, resting on her elbows. “Do you like my big ass Brian. I love having it worshiped, usually by lips and tongues, both men and boys even younger than you. Even better while Roger and I are tongue kissing,” she told Brain as I knelt so we could kiss with our tongues as he smeared oil over her naked ass cheeks.
“Relax yourself first Sarah. I want your calm energy to set the tone for our entire experience today. Is that enough of my special fragrant oil? It will prevent friction and keep my movements smooth and enjoyable,” he told her as he warmed his hands.
“Be patient for me Sarah, intentional, mindful touching is far more relaxing than rushing. I am going to focus on your breathing cues. I want your breathing rhythm to guide my pressure and pace.
“I am going to build gradually Sarah, start softly and increase my pressure only if you are comfortable. I am going to use both hands on your naked body. Do you want my even touch and pressure to make your massage feel more balanced Sarah?”
He started on Sarah’s head and neck. Using his fingertips to gently press her temples and the nape. Massaging in small circles to ease any headache and fatigue. Working on her shoulders and back. Placing his palms on her shoulders, applying gentle pressure, then gliding down along her spine.
Working on her arms and hands. Stroking from her upper arms down to her wrists. Massaging her finger joints to relieve tingling and stiffness. Sarah’s legs had never looked better when he started at her thighs and applied light pressure down toward her calves, massaging her soles to stimulate acupoints and reduce fatigue.
After a few minutes, Sarah was really into her massage. “Tease me Brian, oil and massage my back. So good. Now my thighs. The insides of my thighs. So good. Do you like my man watching? Did you realise he wanted to be naked for both of us while he watched you massaging my naked body? Look at the size of his erection. Big and thick, very thick. Is he that big in the showers at the gym? Now my ass. Give my ass special attention. Very special attention.”
I had to passionately tongue kiss my lady Sarah while I watched the much younger, very attractive, toned boy oiling her magnificent ass, watching his hands all over Sarah’s ass and her obvious sexual pleasure, had given me a raging erection.
“Do you have an erection for me Brian?,” Sarah teased, his erection obvious under his tight shorts.
Just as Sarah and I had planned I fed my erection between her pursed lips while she was having her magnificent, oily ass pleasured by Brian’s oily hands. A huge turn on having my cock sucked by my lady while I watched a much younger boy massaging her magnificent ass cheeks. A bonus turn on for both of us while Brian watched us, distracted from the task at hand.
I watched Brian turn Sarah over, rubbing her abdomen with his palm in clockwise circles while he ogled her damp, honey blonde tuft of pubic hair, staring at it while he told her, “This supports digestion and relieves abdominal tightness.”
He was talking to Sarah in a soft seductive voice, telling her, “Those sexy nipples obviously like my oily fingertips teasing them. There are several vulva massage techniques women commonly prefer Sarah.”
He was using one finger, then two fingers, making small circles around her outer vulva and surrounding tissues, while he told her, “This simple technique encourages awareness and can feel calming. Slow, gentle strokes across your vulva should help promote relaxation and improve familiarity with different sensations. The mons pubis is the soft tissue located above your vulva Sarah. Gentle circles here can feel soothing and can help release tension.
“Some women prefer indirect stimulation through their clitoral hood rather than direct contact with the clitoris itself. Which do you prefer Sarah?,” he asked as he placed a warm hand over her vulva without any movement. “This can create a feeling of comfort and relaxation for you Sarah. Many women prefer this as a starting point before other vulva massage techniques.”
When Brian slid a pillow under Sarah’s ass the massage was far from ethically professional, though very exciting for Sarah and me. I was standing behind her, holding her hands while he was teasing her clitoris with his fingertip. Tempting her, sexually tempting her. Teasing her, edging her with his biggest, middle finger, sliding his finger along her oily cunt lips.
“You know that is not professional Brian. I asked you if this was going to be a professional massage? Or a massage as sexual teasing, sexual foreplay?”
“I have massaged other women while their men watched Sarah. You are the oldest woman I have massaged, twice my age. And by far the most exciting while your man is watching me massaging your naked body.”
Recalling what I had told Sarah, the thought of a man just half your age massaging your naked body while I watch is an exciting thought. What if the masseur wanted to penetrate you with his finger while me was massaging you? How would you respond?
I knew how Sarah was going to respond, how I wanted her to respond, for her sexual pleasure and my own sexual pleasure while I watched the masseur boy sliding his big, thick finger, a finger the size some men’s erection, along her oily cunt lips. Teasing her cunt lips with his oily, big thick finger.
Brian was teasing me almost as much as he was Sarah, while I watched him slowly inserting his big thick finger into her, slowly past the first knuckle, even more slowly past the second knuckle, all the way into her, holding her hands even tighter while I watched.
I couldn’t help asking her, “Is this a professional massage Sarah? Or a massage as sexual teasing, sexual foreplay for you?”
The look of sheer sexual pleasure on her face was answer enough.
I had wanted to fuck Sarah while a much younger man watched for so long. It was a long standing sexual challenge for me. This was the perfect opportunity for me.
“Step aside Brian, your massage technique has turned me on almost as much as you have turned on Sarah. I need to fuck her, now, right now. You can watch if you want to.”
That afternoon Sarah was an incredibly classy, confident, elegant and sexually sophisticated woman for both Brian and me. I had become an addict after my first sexual experience with Sarah – when I visited the meeting of her thighs and dreamed of going back there every night.
From the moment I met Sarah I was intent on seducing her, penetrating her with a finger. Intent on fucking her with my rock hard erection, fucking her with my erection inside her all the way up to my balls. Tease and edge her before I slowly penetrated her cunt lips with my boner. Penetrate her tight, wet cunt lips with an absolute boner.
When Sarah first told me about the flings she had enjoyed with her ‘younger guys’ I was determined to fuck her while a ‘younger guy’ watched. Brian was a little older than her ‘younger guys’, though after watching him massage Sarah, go beyond the ethical boundaries of a professional massage, a turn on for both of us, I wanted to fuck Sarah while he watched.
The massage table was the perfect height for me to slide my erection into her, penetrate her tight, wet cunt lips with my absolute boner. Slowly slide just the tip of my erection into. Pulling back so I could show Brian the masseur the full length of my erection, thicker than the finger I had watch him insert into Sarah.
I had my hands under Sarah’s ass cheeks, lifting her off the massage table while the massage boy watched me slowly slide all of my erection to her, far to good to rush, inserting my rock hard cock into her, all the way up to my balls. Fucking her while the boy watched us. Acting out a joint sexual fetish, playing out a joint sexual fetish, satisfying a joint sexual fetish, fucking her while a much younger man watched.
Afterwards when Brian asked, “To help further my training, would like to receive a massage from one of my female associates, an experienced masseuse, Sarah? I think you would enjoy her hands on your naked body, she is very feminine and so much younger than you.”
I knew Sarah so well, though I was intrigued and unsure if she had ever had a sexual experience with another woman. I had told her many times she was sexually attractive to women, trying to gauge her interest in lesbian relationships. The thought of watching her receiving a full body massage while completely naked from a masseuse would be an exciting opportunity for me to gauge her interest in sexual contact with another woman.
“How about you Roger, to help further with my training, would like to receive a full body massage from one of my male associates, he is a very experienced masseur? I think you would enjoy his strong hands on your naked body, he is very macho and so much older than you.”
“If my offer is of interest to you both let me know by Thursday so I can confirm the arrangements. I will leave it you Sarah.”
The arrangements were in place by Thursday after Sarah told me, “I think I could comfortably receive a sexual massage from another female but I would not want to engage in reciprocal sexual activity with another female. Sounds like you would with another male though. I think males have more of a tendency to bi-sexuality than females.”
On the Friday watching Sarah receiving a full body massage while completely naked from a masseuse was a huge turn on for me. Just as Brian had promised his female associate was an experienced masseuse, very feminine and so much younger than Sarah.
Sarah did enjoy flaunting her naked body for a very feminine and so much younger female she had just met for the first time, dropping her black silk dressing gown to her ankles, fully aware her cougar body was attractive to most females.
The masseuse had her hands on Sarah’s naked body, she was so comfortable receiving a full body massage from another female, though she didn’t engage in reciprocal sexual activity with her. Though she did enjoy receiving a teasing massage from her before her massage became a teasing, sexual massage.
“I think you would enjoy your massage more if I was naked for you Sarah, I don’t expect any reciprocal sexual activity, that would be unprofessional, unethical even.
“Just relax and go with flow Sarah. I would love to seduce your sexy, cougar body, though that would be unprofessional, unethical even. If my massage becomes sexual teasing or sexual foreplay, tell me and I will stop. Or alternately imagine it is a man my age massaging you. Will your man be comfortable watching me massaging you? Lots of men have watched me massaging their wives or mistresses.
“Some women like to talk about their sexual preferences while I massage them. A good massage should feel relaxing, comfortable, and natural Sarah. To massage you properly, I am going start with your big, cougar ass. I want you to remember the best massages are calm, attentive, and never rushed.”
“Will you to behave professionally while you massage my naked body. Will you be professional for me? Do you promise you won’t try to seduce me while I am naked?,” Sarah taunted.
I was almost naked while I watched, I wanted to talk to Sarah while I watched her masseuse giving special attention to Sarah’s wonderful, naked ass.
“The first time I ever sited Sarah’s naked ass was after we fucked for the first time. I am still not sure if she did it deliberately, she was naked with her back to me as she dressed after a shower. Up until that moment I never realised I had an ass fetish. From that moment on I can’t have enough enough of her beautifully proportioned big ass, size-10 on a size-8 body. Just magnificent, fucking magnificent,” I told the masseuse while I watched her oily hands all over her naked ass.
“Sarah’s body is still good, men and young boys love her legs and ass and the way I trim her pubic hair - less is more. Sarah and I both have a high sex drive, very high, Sarah is to please and be pleased sexually, she loves being licked and teased by men and boys, she lost all her inhibitions between her second and third husbands and she loves having sex with an audience. And she really does enjoy some racy commentary during sex, an extra dimension for her.”
The body language of Sarah’s masseuse was becoming unprofessional, she wasn’t professionally detached while I watched her massaging my lady’s naked body. Giving her sexual pleasure with her experienced, hands and fingers.
“You did promise you wouldn’t try to seduce me while I was naked, I don’t mind, don’t stop, keep going. That is so good. You know what I want, what I need.”
The masseuse was using one finger, then two fingers, making small circles around Sarah’s outer vulva and surrounding tissues, “Some women prefer indirect stimulation through their clitoral hood rather than direct contact with the clitoris itself. Which do you prefer Sarah?,” she asked as she placed a warm hand over her vulva without any movement. “This can create a feeling of comfort and relaxation for you Sarah. Many women prefer this as a starting point before other vulva massage techniques.”
“I have massaged other women while their men watched Sarah. You are the oldest woman I have massaged, twice my age. And by far the most exciting while your man is watching me massaging your naked body.
“Relax Sarah, let my fingers massage your cunt lips, bring you to a climax. Is this what you want? Yes?”
It was exactly what Sarah wanted, a long slow, wet climax, and exactly what I wanted to watch, visual foreplay for me.
“How about you Roger, to help further with my training, would like to receive a full body massage from one of my male associates, he is a very experienced masseur? I think you would enjoy his strong hands on your naked body, he is very macho and so much older than you,” the masseuse asked while I watched her hands running over Sarah’s naked body.
“Yes I would like to receive a full body massage from one of your male associates. Can you tell me some more about him?”
“No need to, he just walked in the door.”
Jonah was a visually exciting man for me, ten-years older than me. I had been anticipating him massaging my naked body for what seemed like an eternity though it was less than two two weeks.
“Will you be professional for me? Do you promise you won’t try to seduce me while I am naked? I am not gay, I am bi-curious, pansexual, essentially I am attracted to sexual pleasure from all genders.”
I was naked under my black satin dressing gown looking directly at Jonah, when I let it fall off my shoulders, enjoying him looking at my already tumescent cock, Turning to show him my ass. I wanted to maximise my sexual pleasure while I received my massage.
“I am going to enjoy giving you a massage, I haven’t had a man your age to massage for so long, though in the past I have massaged men your age, and much younger men, teenage boys even. Your macho body will be a special challenge for me.”
“Is this going to be a professional massage? Or a massage as sexual teasing, sexual foreplay?,” I asked, the tone of my voice letting him know I was open to some sexual teasing, sexual foreplay, as he organised me on his massage table, running his hands over my chest before I settled on his table.
My naked ass was pointing to the ceiling, my masseur was admiring my naked body while I watched him pour fragrant oil into his hands, smearing it all over my back, massaging my shoulders, my back, before he poured more oil over my ass, letting it slide into my ass crack, before ran his fingertips over my ass. Pummelling my ass with his fists, slapping it with his hands. Lifting my ass so he could massage it harder.
When he turned me over I had a grade-10 erection for him, though he ignored it, standing behind my head, oiling my chest, special attention to my nipples. How did he know that was one of my major erogenous zones?
“Your big cock is far more impressive almost any man I can recall. You told me you weren’t gay, just bi-curious, pansexual. I know exactly what what pansexuality is, would you like me to give you a pansexual hand job? Ethically it won’t be a professional massage, just a massage as sexual teasing, sexual foreplay,” he told me with his hand wrapped loosely around my erection.
Wow, he was so good, talking to me while he expertly masturbated my erection. “When was the last time you fucked your lady? Would you like some more oil? She is an absolute cougar baby doll. Does she masturbate you like I am? Is she as good as me? Does she give you head jobs? Does she give you hand jobs? Some more oil on your balls? Are her hand jobs as good as mine? Or as exciting as mine? Harder or softer? Harder, yes? How much harder? As hard as that?
“I am sure you know an experienced masseur understands the nuances of a man’s sexuality, what he expects to maximise his sexual pleasure. To maximise his orgasm. What he expects from another man? Would you like your naked lady to kiss you while I bring you off, bring you to orgasm with my hands? Tease and edge you to orgasm?”
Sarah did kiss me with her tongue, so erotic, while he teased and edged me to orgasm, massaging (or was it sexual teasing) the ridge under the tip of my erection. Edging me, making me wait, edging me some more, making me wait some more, this wasn’t a massage, just high-end, drawn out, erotic sexual pleasure.
A few months later we heard Brian, our original masseur and his associates had a flourishing new career in the massage industry, specialising in high-end, premium price, massages and hand jobs for females and males while their partner watches.