Part 1: TGIF
"All Friday night, just good, clean, naughty fun," she purred into the telephone line. That’s how the whole thing started.
I had been dating Bettie for about three months. A woman with a nice body and a warm, generous personality. Fair skin, dark hair with cute bangs. We were in our early thirties, and super compatible. We were both a little wary of relationships; we both had had one lousy childless marriage in our pasts, and we had been alone the previous few years, just drifting along when we found each other. I worked for an insurance company that did business with her large banking firm, where she was an executive. We worked on a brief project together and started dating.
We didn't jump into bed right away; we took our time getting intimate and though she seemed a bit reluctant to “let go” at first, our sex life was building recently and getting steamy and I considered myself a lucky man.
The previous weekend, at my place, she confessed that she sometimes liked bondage and convinced me to tie her hands behind her back with a piece of rope she had brought, and also blindfold her with a sleep mask. I had gone through a brief but intense bondage-based relationship about ten years earlier, so I knew where the knots went. She softly writhed and moaned when I held her from behind, caressing her breasts and fingering her already-damp pussy.
She reciprocated by using her bound hands to fondle the bulge in my pants. (She wanted to be naked, while I was still clothed.) Man, I wanted to take her right there and then, but I took my time, bringing her to a shuddering orgasm with my hand. At that, she went a little weak in the knees, so I eased her down onto the carpet. I then offered her my cock to suck as she knelt, and although it was a little awkward with her hands behind her, she did her best, which was very nice. I then put her on the bed and drilled her from behind while she was still bound and she liked that, too. Another orgasm for her, and one for me. I untied her, we held each other, and the rest of the weekend was intimate and warm. The bondage session seemed to break a little dam in her inhibitions. Maybe mine, too.
Cut to the following Thursday and we were on the phone, making plans for the weekend. She had been busy all that week with her job and with helping a friend from work named Page put on a party for her 18-year-old twin daughters. She wanted to make it up to me for the few days we had spent apart.
"The party is tonight, Kevin, and then I'm all yours, from Friday on. We can stay at my place and I'll treat you... " She paused.
"Treat me to what?" I asked with a smile.
"Let me do to you what you did to me last week," she blurted. "I've got some new lingerie I know you'll like, some new body oil. I'll be good to you, baby."
My cock stirred at the image, but I was a little hesitant to push the kinkier aspect of our affair too fast. That had burned out that past relationship with a somewhat older, more aggressive woman in the past, and I saw Bettie and me as a long-term thing. She understood.
"I won't go crazy on you. No pain, no humiliation. All Friday night, just good clean, naughty fun."
I agreed, and so the following warm summer evening, after a nice dinner, a Viagra, a couple of drinks and a shower, I found myself tied eagle-spread to her bed with comfortable Velcro wrist and ankle cuffs she had bought, with only a towel around my waist to cover my manhood. The lights were low, soft old-school R&B music was playing and Bettie had just changed into her lingerie, a blue satin teddy. She was just starting to stroke my chest when her doorbell sounded. She didn't seem very surprised. Slipping on a robe, she said, "Be back in a minute. Don't go anywhere."
Before I could stutter out my WTF, she had gone down the stairs to the front door. I heard the faint giggles and whispers of female voices, and then two pairs of footsteps coming up. Bettie walked in and said, “We have company. I hope you don’t mind.” Behind her was a lovely woman with wavy brown hair, in a short but stylish summer dress that showed off a nice figure. As they approached, I was startled to realize who she was.
“Hello, Kevin,” she said softly. “It’s been a long time.”
“Jewell?” I asked. This was the woman I had had a brief but intense relationship with ten years previously. Her appetite for bondage, drugs and kinky sex (kinkier than I was ready for at the time) had scared me off.
“Jewell was the alter ego I was using back then,” she smiled. She had a marvelous face, with bold features that always reminded me of that sexy actress in the movies Bound and Showgirl. “I’ve been just Page for a while now. After our fling, I realized I had to dial back the wild times and take care of my little girls more responsibly. They liked their mommy’s boyfriend Kevin, and still remember how you played your guitar for them and took us all to the water park and the movies.”
I remembered her two young twin girls, pretty and vivacious, always ready with plenty of hugs and kisses for me. They were great, but I was not ready to be a step-dad formally or informally at the time. The other thing that made me step back was Jewell’s increasing push for heavy bondage games and kink when the kids were away, staying with their aunt.
I remembered the one Saturday night that found me standing nude in her basement, arms bound to the rafter above, ankles apart with a spreader bar. Jewell had her hair slicked back in an androgynous style. She was dressed in a short, open leather vest that barely covered the nipples on her naked breasts, along with leather boots, black leather chaps and a holster. She was also sporting a big strap-on dildo on her naked crotch. Beside her, on all fours and on a leash, was a naked, collared woman that I had never met, who I gather was going to pleasure me or torture me from the front while I was being whipped and pegged from behind by Jewell.
I had been learning a lot about bondage and sex from this more experienced woman in our few weeks together. (I had spent the previous night learning from Jewell how to tie her up in various ways and give her the rough sex she wanted.) Now, we normally discussed in advance the outlines and boundaries of the wilder sessions, but she surprised me with this scene. She was high on something, and this was too much. I gave my “stop now” safeword, she let me down, sent the woman home, and we talked. There was no animosity when I packed up my overnight bag and left, but I had completely lost contact with her in the years since then.
“Jewell, er, I mean, Page,” I finally sputtered out. “What’s going on? Why are you here?”
She sat beside me on the bed, where I lay, still bound on my back. She said, “When you left, I gave up the wild partying and dating and bondage, went back to being just Page. We moved to a good school district and I raised my daughters to be modest and kind. They’re smart and beautiful, and both have sports scholarships for college this fall. In the past two years I’ve been very frank about my wild times, and the drawbacks that that life entails. I’ve steered them away from being intimate with boys as much as possible. Oh, they’ve each done some kissing and such, but they’re both virgins and they plan to stay that way until they get married or at least really serious with a mature man.
“When Bettie told me about you, Kevin, and showed me your picture, I realized you were the one that influenced me to turn my life around. I could have died from the drugs or lost custody of my little girls and I thank you for that.” Bettie had her hand on Page’s shoulder. Page reached up and caressed it. “Bettie and I have been close friends, discreetly, for the past year. I am so happy for you both, and now I have a favor to ask of you. The girls liked you, Kevin. They had a bit of a schoolgirl crush on you back then.” She leaned forward and whispered, “And they still do.”
She stroked my torso, lightly fingering my chest hair. “Before they go to college, the girls want to have some experience with a man. They’ve read books, they’ve seen videos, but they want to study his anatomy, learn how to please him and be pleased in return. They’re not looking for intercourse, but want first-hand experience so when they do meet the men they love, it won’t be awkward and clumsy. Since you’re tied down, they’ll feel safe in exploring what I remember is a very nice package. And you’ll be safe from any suggestion of forcing them into anything.”
Bettie asked me, “Are you ok with that? I am. The girls are downstairs waiting. We’ll be here to show them how to do everything and keep you safe. Just good, clean, naughty fun.”
“Damn, woman,” I said. “You are just full of surprises.” Page’s hand had wandered down to the area of the towel that still covered my cock, running a finger over it. I was rock hard. The younger Kevin would have backed away, but now . . . I considered it. Trying not to let my penis lead me astray, I looked into the faces of the two women and found no malice, no guile. I drew a breath and decided. “Sure, let them in.”
Bettie and Page both beamed. Page called out, “Come on up, girls, he said yes.”
Yips and giggling sounded from the staircase. Two nearly identical girls came into the room, fit and pretty. Both were barefoot, with athletic legs, strong arms and tight abdomens. I could tell because each wore gym shorts and fetching crop tops. Their hair was moderately long and in ponytails, one kind of blonde and one darker. They smiled coyly and wiggled their fingers in a hello wave.
“Kevin,” said Page, “You remember Ashley and Renee.”
About an hour after the introductions, the session came to a climax. Or at least I did, in a spectacular fashion, spurting a big load of cum all over my stomach and chest, as the two girls oohed and aahed. Both girls were topless by this time, displaying their wonderful, firm C-cup breasts.
The “class” had started with Page explaining that men get aroused by visual cues. The girls were excited but a bit uncertain, so Page started things off by taking off her sundress (slowly, in time to the soft music) to reveal a sheer black bra, panties and garter set. The girls took off their tops, showing off gorgeous lace bras; Ashley in pink (she was the blonde, must remember who's who!) and Renee in light blue.
They moved on to kissing and foreplay. “Try to get your boys to start with close-mouthed, soft kisses and work your way up to the more passionate tonguing,” Page said, while Bettie demonstrated on me. They all kissed me and moved on to using their mouths on my ears, neck, chest and stomach. At one point, there was a teenage girl on each side of me, licking and nibbling my nipples. I was turned on and aching for someone to touch my cock. Good thing I was still tied up or I’d be grabbing flesh all around.
Eventually it was time for the big reveal. Bettie did the honors and pulled off my towel and my hard cock was on display for inspection. The elephant in the room was the large dose of pre-cum oozing out of the tip. Page had the girls touch and rub it between their fingers, explaining that while it served as lubrication, it contained some sperm, so it should be treated as potent semen. (The girls were on birth control, but there would be no intercourse for these two virgins.) She handled my package, naming the various parts of my cock, balls and anal area, then pulled out an electric grooming tool.
“Kevin has already trimmed his pubic hair - thank you sir - but we can do better. Girls, doing this for your man will show you care and also make things nicer and neater for you.” Page carefully clipped and said, “One of the learning materials I showed the girls was an old copy of 'The Joy of Sex’ from the seventies. Renee looked at the drawings of the nude couple and asked, 'Didn’t they have razors back then?’ It was a different time, ladies, a different time,” Bettie joked, “What’s that line from that show? ‘Not so much a landing strip as an abandoned airfield?’” They all chuckled, but I was focusing on trying not to get carried away and erupt as she handled my manhood.
Then the young women learned how to fondle male genitals, the first they had actually touched. (At least that’s what they said.) “Find out how much handling his balls can take,” said Bettie. "Testicles are somewhat sensitive, so take it easy and watch for body language cues.”
“Yes,” chuckled Page. “Cock and ball torture comes later in the curriculum.” My eyes widened. Page laughed, “Kidding, honey. It’s all about handiwork today.”
Flashback: The talk of CBT brought back memories of a roleplay session she talked me into years ago. Firmly tied to a chair, I was a naked prisoner being interrogated by an enemy military officer. Wearing camo bootie shorts and a crop-top camo shirt, she knelt in front of me and tied up my genitals with shoelace material. She then ran a spiked pinwheel over the sensitive skin of my cock and balls (also my thighs and nipples) while asking me to reveal a code to open a locked briefcase. She also applied some nipple clamps that vibrated. Per her earlier request, I resisted for several squirmy minutes, pretending it was absolute agony, though the sensation actually was both painful and exciting.
“You are so brave,” she purred in a Russian accent, standing up and kissing my mouth and face. “No one has taken this much punishment before, ever.” She fondled my cock. “Every man in this chair has broken eventually. So, tell me the one little thing I want to know right now and the pain will end . . . and the pleasure begins. I want you so badly.” I assumed that was my cue to give up and I gave her the code. She placed the “boobytrapped” briefcase on my lap and observed, “So sad. If this blows up, you won’t have anything for me to suck on.” She opened the case successfully, kissed me and then gagged me, and proceeded to administer a long, wet, teasing combination hand job/blowjob.
Back to the present:
Page explained the need for lubrication, and she had a bottle of it, but told the girls that spit also works to start things off. With some giggles, the four women took turns spitting and drooling on my cock, making it a kind of contest to see who could produce the most saliva. They rubbed it in. I was still tied down, still going crazy with lust, almost ready to cum, so Page backed off and slowed the touching down a notch.
“I think it’s time to show him what we’ve got up top.” Page and her daughters each took off their bras to reveal very nice tits. (Page’s D-cup breasts were a bit larger than the girls, but still firm and stellar.) No tan lines showing, they must sunbathe topless or nude. Bettie was still in her teddy, but pulled down the top to reveal hers as well. She leaned over me to let me suck her nipples, and the other women followed in turn.
Ashley then got between my legs and with a little extra lube, started stroking my cock. Page gave expert tips on how to manipulate the glans, the frenulum, the perineum and the shaft, while Renee took occasional turns from the side. “When he’s in a more favorable position, I’ll show you how to play with his anus and prostate. You’re doing a good job, Ashley. Now get your face in closer. Let him feel your breath on his cock. Blow on it. Watch his reaction. Look at him lovingly.”
She did so, while stroking, and I just could not hold it. I moaned and cried out and Page called out for her daughter to keep going. I gasped and spurted my load. Ashley pulled back just in time to avoid a face-full.
As I caught my breath, the release of sexual tension (along with the continued stress of the bondage I was in), caused me to burst out laughing. When had that happened before, I asked myself? Oh, yes, back that night during the interrogation scene. My laughgasm started the others breaking up and I think it broke a layer of ice for the teenagers and us adults.
“Me next,” Renee called out excitedly, like a child at Christmas.