I was in my mid-thirties when I moved into a high rise building overlooking the ocean in a sub-tropical major resort city. It was also a most popular location for retirees. The building had no road between it and the ocean, so it fronted the ocean, all access was by a long drive from the rear of the building. The majority of the residents were retired couples, with a large number of single women.
I quickly learnt some of the single women were still sexually attractive, two in particular. I used to walk bare chested and suntanned past the pool on my morning walk. On Thursdays there was always an exercise class of some sort in the pool with a woman shouting instructions to a group of women. Invariably some of the women would look closely at me and call out ‘good morning.’
If I was a little early on the Thursdays I could look the women over before they got into the pool. The majority of the women were past being sexually attractive, with a few notable exceptions.
In due course I fell into conversation with Elsa, one of the women who had greeted me with a cheery, ‘good morning’, dressed in a one piece bathing suit as she lay back tanning herself. Lot’s of two way questions, quickly learning she was a lonely widow.
“My girlfriend and me return at eleven to sunbath, why don’t you come along and talk to us?” I did join them, Elsa and her friend Zali. Admiring their lush, mature size 12-14 tanned bodies in tight fitting, one-piece swim suits, wonderful firm, fleshy thighs and enough generous cleavage to convince me the two older women still had magnificent tits.
Turning to lean on their elbows before Elsa asked me to oil her shoulders, then her back as she managed to expose it for me. Wishing I could oil her obviously big ass concealed under her costume as I oiled her thighs, then the insides of them as she opened her legs for me.
Elsa so confident while talking to me all the time, confiding in me, telling me she was a wealthy widow after her older husband died more than a year ago. Her hand behind her back, slipping her bathing costume into the crack of her ass, exposing it for me so I could oil it. Wow, what a waste on a fifty-year old widow. The ultimate tactile feel surely, my hand on her magnificent big ass, then two hands all over it. Forcing my clenched fists into it, relaying pressure to her vulva.
Elsa suggested we move to a more secluded spot, the dress optional area, sitting on a chair, sliding the top of her costume down to expose a magnificent pair of tanned, slightly saggy tits for me, her girlfriend Zali watching on, admiring her tits almost as much as me. Standing behind her sitting in the chair, my large hands oiling her tits and nipples. Hoping the two women were aware of my erection straining against my bathing costume.
Later over coffee with Elsa I told her, “I am very attracted to you.” Reading her body language before I continued. “Your wonderful lush body is a turn on for me.” Holding her hands, carefully studying her body language some more before I told her, “I had an erection for you earlier.” Hoping I hadn’t overstepped.
“I know you did, so pleased I can still turn on a man, a younger man especially. I haven’t had a man since my husband passed. Would you like to be the first?” Kissing with our tongues across the table.
I was so pleased to be the first after she took my hand and led me to her unit. My erection under my slacks obvious to those who looked, our intentions also obvious to them, an older woman about to enjoy a mutual seduction with a younger man. My ego in overdrive.
And enjoy it we did, kissing passionately with our tongues as we removed each other’s clothes. Admiring each others naked bodies for the first time. Flattering me when she told me I was huge, much bigger than her husband. Feasting on her magnificent pair of slightly saggy tits. Nipples to die for, licking and sucking them. Whispering to me, “I hope you like my 36D tits.”
Telling me, “My husband never did that to me, as I licked and kissed her big ass, clenching it for me as I worshiped it, the few sexy dimples an extra turn on for me. “My ass likes it, you kinky boy. What have I been missing?”
Placing her on chair, opening her legs for me, licking and kissing my way up her wonderful creamy thighs to her sexy, thick black pubes, my tongue finding her clit. Elsa moaning, “Oh fuck yes, my husband never did that to me,” as I showed her what a clitoral orgasm was.
Elsa urging me to fuck her like a woman who hadn’t had sex, a fuck for years. In the afterglow, telling me, “My husband never fucked me for as long as that.”
Telling her later, I wanted to shave her copious bush, explaining what I wanted her pubes to look like, offering her a few choices. “My husband never did that to me, I like it. I can’t wait to show and tell my girlfriends at the pool,” she smiled as she posed in front of a mirror.
Fucking for the second time that day. Telling Elsa to fuck me while on top, her big ass facing me so I can admire her ass, hold it in my hands as she used me.
The next afternoon showing Elsa how I like to have my cock sucked. My cock flaccid when she commenced, an extra turn on, admiring her naked big ass in the mirror behind her. Talking to her all the time, explaining my ass fetish to her, complimenting her on her head job skills. Holding and moving her head so she was edging me. As I was almost ready to blow,, telling her I wanted her to swallow. “Oh wow, so good I never did that for my husband, you kinky boy.”
Introducing Elsa to my cock rings, showing her how to fasten them around my balls, Shopping with her for vibrators, sexy lingerie, stockings and garter belts. “You have the perfect body for black stockings and garter belts, and the perfect ass for garter belts,” I told her while I watched her trying them on, making sure the female shop assistant also had a look at her dressed like that.
Elsa insisting on unwrapping her new purchases as soon as we returned, “Heels, stockings and a garter belt, nothing else,” I told her wanting to fuck her immediately in her new outfit.
“I never dressed like that for my husband, he wouldn’t let me. I like it, I always wanted a garter belt and stockings. Does my ass look big?”
“I told you in the shop, you have the perfect big ass for garter belts, look how hard I am for you.
After a few weeks Elsa told me, “My girlfriend Zali is jealous, you have taken me away from her. Would you mind if she came to dinner with us?” I didn’t mind at all, perversely hoping I could make her girlfriend even more jealous. Also hoping the dinner that night might become sexual.
I learnt Elsa’s girlfriend was also a wealthy divorcee after her husband took off with his secretary. Over desert Elsa telling Zali about our sex life. Instead of lessening the jealousy, Elsa increased it. “Scott does sexy things to me my husband never even dreamed of.”
Holding her hand as she continued, “He worships my big ass, licking and kissing it as foreplay before he licks my cunt, tongue fucks me. And when he fucks me with his thick, hard erect cock he is so good. And so big!”
By then it was obvious Elsa wanted to have her girlfriend Zali involved. Kissing her with her tongue, asking in a whisper, “We had intended to make love and fuck around this time tonight. Would you like to watch?”
A new and exciting dimension for our relationship as Elsa’s girlfriend watched her undressing and changing into her heels, stockings and garter belt. “I hadn’t told you Scott shaves me. Perhaps he could shave you Zali? Does my ass look big in my garter belt?”
“Did I tell you Scott has an ass fetish, that I like him worshiping my big ass? So good, I love it and so kinky for me. Did your husband worship your ass like that Zali? Am I turning you on?”
“You know you are turning me on you bitch. I have wanted to have you, make love to you since the moment I met you,” Zali told Elsa, kissing her passionately. Elsa helping Zali to undress, incredible sexual attraction between the two women, outright carnal lust.
“Scott loves fucking me from behind with my big ass in his hands. We both wanted you to watch.” Zali was making love to Elsa while I fucked her from behind. Kissing with their tongues. Sucking her nipples, licking and kissing her tits. A wonderful sexy vibe.
An hour later after the three of us had showered together, it was Zali’s turn to make love to Elsa, tongue fuck her. How could Elsa not have realised her girlfriend was bi, a lip stick lesbian?
Elsa sitting in a chair, me standing behind her, kissing her over her shoulder as Zali prised her legs open, licking and kissing her wonderful thighs with her arms wrapped around them. Sliding her tongue up to her clit.
Elsa and me kissing with our tongues as Zali showed Elsa her lesbian skills. The first time in my life I had watched two women making love, having lesbian sex.
“I want to watch you fuck my girlfriend Zali,” Elsa told me later that day, though instructed would be a more apt than told me. “I am living out some of my long held sexual fantasies with you. Something I could never do with my husband.”
“I want to sit back and watch you with Zali. I told her she has my permission to fuck you Scott. I never imagined when I first met you we would be in a situation like this.”
At two the next day, by now I have convinced Elsa afternoons are the best time for sex, Elsa and me were preparing for Zali. “I have never ever watched a man and a woman making love, fucking. So exciting when it will be my years younger male lover and my bi-sex lesbian lover. Do you want me naked while I watch? Perhaps almost naked in my lingerie?”
When Zali arrived Elsa greeted her most enthusiastically, both of them kissing with their tongues, before Zali gave me her full attention. “You are such an exciting man for me. Now that Elsa and me have established our sexual relationship, I want to share her with you. Undress me while Elsa watches.”
Zali completely naked for us apart from her heels, after I removed her dress and sexy black bra, licking and sucking her nipples and tits as I did, then her sexy black thong, a hand on her big ass, my other hand sliding over her shaved bush. Elsa watching all the while wearing heels, stockings and a garter belt.
I was sitting on the couch as Elsa watched Zali slide herself onto my erection, my hands grasping her big ass, as she commenced fucking me, her nipples and tits close enough for me to suck. I could see her ass in the mirror opposite with my hands holding it. What a pair of hips! Elsa watching intently as she ran a hand down Zali’s back, then over her ass. So tactile.
Elsa sitting on the couch alongside us while we fucked. Zali leaning over to kiss Elsa while she continued fucking me. Elsa kissing me while her girlfriend was riding my erection, fucking me. Then Zali tongue kissing while she fucked me, whispering, “Fuck me, fuck me, fuckame, fuckamycunt.” Elsa masturbating while she watched.
The three of us so comfortable in a three-way. All of us determined to develop and stretch our relationship.
The morning I oiled Elsa’s naked body on the massage table while Zali watched was a standout. Elsa lying face down completely naked as I commenced oiling her body, her shoulders, her back, her thighs, the insides of her thighs, then her big, firm ass. Teasing Zali while she watched, as I talked to Elsa. “My hands love your magnificent big ass. So does my cock. Your naked ass has given me an erection, a real boner.”
Turning her over so I could oil the rest of her body. Shoulders, thighs, the insides of her thighs, then her nipples, just a light touch so they responded for me and Zali, oiling Elsa’s wonderful tits, then her stomach down to her freshly shaved pubes. Spreading her legs, teasing her clit with the oily tip of my middle finger.
Zali naked now, laying along side Elsa on the table. Kissing with their tongues as Elsa’s clit responded. Whispering to her, “I am going to finger fuck you, make you squirt for me.” Licking and sucking her nipples while finger fucking her as Zali kept on kissing her.
Elsa lifting her hips so I could place a pillow under her ass, licking and sucking her cunt lips, before I resumed finger fucking her. My finger finding her clit. So wet for me. “My husband never did that to me, to my cunt, never. Don’t stop. Two fingers.”
Zali sitting on Elsa’s face, positioning herself so Elsa can lick her, tongue fuck her. Alternating sliding one finger, then two fingers into Elsa, determined to make her squirt for me. I also wanted to make Zali jealous, jealous enough that I could do the same to her. Reverse the situation with Elsa watching.
Teasing and edging Elsa, two fingers inside her, the tip of the thumb of my other hand teasing her clit, her body trembling, fighting to hold back her orgasm. “Oh fuck yes, yes, so good,” Elsa moaned as she orgasmed and squirted, Zali and Elsa kissing with their tongues.
I had a rock hard erection after that, needing relief. Prepared to masturbate if need be. By now the three of us were so comfortable with each other. Zali telling me to take her place on the table, bending over me, using two hands to masturbate me, Elsa and me kissing with our tongues. Edging me, bringing me to a shuddering orgasm with her lips, tongue and mouth as Elsa and me kissed like never before. Life is good!
The most incredible sex with the two women. I was sitting on a low stool, tongue fucking Elsa, my hands grasping her big ass while her friend and lover Zali simultaneously gave me a head job. I thought sex couldn’t be better than this until one night the two women laid me flat on my back. One teasing my cock to erection while the other licked and sucked my nipples.
Then one sitting on my face, my hands grasping her big ass while she looked down on her girlfriend sliding onto my erection. Kissing each other. Could my sex life be better than this?
It could be, I quickly learnt. These two women were on a mission to catch up on the sex they missed out on. Zali had asked me a few times with Elsa listening, if another man had ever given me a head job. My non-comital smile every time answer enough for them.
One day Zali told me her cousin Chandler was in town for a modelling assignment. Asking if Elsa and me if we would like to see his pics on her phone. “I told Chandler I had met a very virile younger man and asked him if he would like to meet you Scott. Would you?,” she asked as she scrolled through the pics.
Chandler was a very pretty boy, around twenty-five, his make up immaculate. A cross dresser with an attractive body, wonderful legs, short cropped blond hair and a very effeminate appearance. Dressed as a female in heels black lingerie, a bra and knickers with an obvious erection in some of the pics.
Elsa was just as interested as I was when Zali scrolled through Chandler’s pics a second and third time. “I think I know you well enough by now Scott to feel sure you would like to meet him. Could you get it up for him with Elsa and me watching?”
“You do know me very well Zali, you also know I live a challenge and being challenged, I would love to meet Chandler. With you and Elsa present,” I answered as I Elsa smiled at me, confirming she wanted this almost as much as I did.
The next day at three in the afternoon when I arrived, Elsa and Zali were sitting together on the couch, holding hands. They were both dressed in their sexiest outfits. Heels, stockings, garter belts and cup-less bras. Lots of wonderful semi-naked flesh on show for me. And for Chandler?
I was naked under my jeans. A little earlier Elsa had oiled my back and torso. Whispering to me, “This is so exciting for me. My husband and I never thought of watching a man giving a head job to another man.”
Just as I had expected Chandler made a dramatic entrance. He was a very exciting boy in the flesh. dressed as a schoolgirl, in a short flared skirt, low heels and a white blouse: He and me staring at each other, not a word spoken, ramping up the sexual tension, before Zali removed his skirt and Elsa removed my jeans for me. My legs spread, hands on hips, flaunting my cock for Chandler and the two women. He doing the same for me. So pleased my cock was much larger than his.
Zali standing behind Chandler, removing his blouse, teasing his nipples as Elsa stood behind me teasing my nipples. Knowing that was a sure fire make to give me an erection, a real boner. Chandler and the two women watching my cock grow.
Even more exciting when Elsa stood being Chandler and Zali stood behind me. They had obviously done some planning in the lead up.
I was standing, always the best position for a head job, with Zali standing behind me, as Chandler took my erection between his lips. I could feel Zali’s pubes grinding into my ass as she kissed me over my shoulder.
Elsa with her hands on Chandler’s face, guiding his head along my erection, feeling my erection in his mouth with just a fingertip on each of his cheeks.
A head job from a talented boy was such an exciting change. Chandler edging me to orgasm, slowly, expertly he really was talented. Lots of subtle touches. Wanting to tease the two women as well as me.
Both of the women muttering, “Oh wow,” as he sucked my balls, my erection like an iron bar. Even harder as he edged sucked me to an incredible orgasm. My first ever with two women watching, two of my cougar lovers.
Later Chandler had Elsa excited, and me, whispering to Zali, “My husband never watched a man, a boy, tongue fucking me, giving me cunnilingus, with another man and woman watching. That is so good while my man is tongue fucking my girlfriend.”