Eight Day Hanuah Challenge

Eight-day Hanukkah Challenge

From the time she tried to blow me at my Bar-Mitzvah to now, our second year in college, I always knew Susie to be wild. She wasn't Jewish like me, but since we hung out together from childhood, she knew many of our traditions and celebrated our holidays with me, except for Yom Kippur, the holy day of atonement. She insisted that since she wasn't religious, she didn't have to ask forgiveness for anything she did.

Shortly after Thanksgiving break, we sat around with friends, smoking weed and contemplating some fun after the semester's final exams. The conversation turned from holiday traditions to sexual proclivity.

"Your problem, Randy, is that you've only ever fucked one girl," she teased me. Susie was the only girl I did have sex with. Although our relationship was more of a friendship than a romantic coupling, she sometimes took pity on me and insisted on reliving my sexual tensions.

"Is that a Jewish thing?" Jenny asked. As evident from our earlier discussion of holiday traditions, I was the only Jewish boy in our circle of friends. Jenny had adopted celebrating Kwanza, which, like Hanukkah, took place over many days. "I mean, being so unsure of yourself that you can't just enjoy sex for the pleasure of it?"

"Wow, Randy, she's diggin' into you hard," Susie shot at me.

"I'm not a whore like some people I know," was my lame response.

"So, I've got a new spin on celebrating the holidays this year," Susie said excitedly. "This year, I challenge you, Randy, to fuck a different girl on each of the eight days of Hanukkah."

I was stunned. What a crazy thing to propose for me. I couldn't get one other girl than Susie my whole life, and she only fucked me out of pity. It wasn't that I was ugly or fat. I always worked out and took care of my body. I was just so unsure of myself. Girls were not attracted to my lack of confidence. I suppose I just accepted that, and someday, I'll meet someone who will understand me and want me anyway.

I watched Susie whisper something in Jenny's and Karen's ear. They seemed to perk up all of a sudden.

"I'll take day one," Karen called out gleefully. Her boyfriend gave her a dirty look. "Don't get jealous, Kenny. It's just for fun and to help Randy gain some confidence," she told him, though I don't think he was all right with it.

"Then, I'll do day two," Jenny chimed up. "I'll give you a taste of chocolate you'll never forget."

I was still speechless. What did Susie get me into? I couldn't back out, not with the peer pressure on me. I must have had a fearful expression when Susie tried to reassure me.

"I'll be your

shammash

. Isn't that what they call the helper candle on the Menorah?" she asked innocently. I didn't know what she meant by being my helper. Was she going to help me get girls to have sex with? Was she going to coach me? How was this going to work?

Later, when we were walking home, I asked Susie what she had whispered to the girls to make them volunteer so readily.

"I told them how thick and hard your circumcised cock is. I told them how good it feels to have my pussy stretched," she responded casually.

**************

Christmas and the first day of Hanukkah fell on the same day, December 25

th

. As my 'helper' in the challenge, Susie arranged for us to meet with Karen and her boyfriend Kenny, at Karen's apartment near the campus. I was concerned that Kenny would be there, but he insisted, stating that if Karen was going to have sex with someone besides himself, he needed to be there. Susie and Karen didn't mind, but I wasn't sure how comfortable I'd be in that situation.

"You've been naked with other men in locker rooms. So, why are you freaking out about Kenny?" Susie tried to calm me down.

"Yeah, but we don't have hard-ons in the locker room," I told her.

We smoked weed to get relaxed. Then Karen took the initiative to come on to me. I assumed she had discussed the seduction details with Susie and maybe with Kenny; he seemed to be taking it easily.

Karen knelt before me, pulling down my pants and boxers, taking my cock into her mouth. She felt different from the way Susie sucked me, and I quickly got hard. I gestured for her to pull back so I wouldn't come quickly.

I finished undressing, watching Karen strip. Her body was thicker than Susie's, enticing differently. Her large, malleable breasts were fun to play with. I sucked on her nipples, eliciting soft moans. Susie and Kenny were already making out naked on the bed when we joined them.

"Eat her out," Susie whispered in my ear. I didn't require encouragement. Her sopping wet pussy tasted good. Her clit was easily found, having swollen to a discernable nub, begging to be sucked on.

Susie came several times, bathing my face in her hot juices. "Fuck me, Randy," she cried out. "I want your thick cock in me," she begged some more. She spread her legs, beckoning my cock to fill her hot pussy. I thrust into her out of an uncontrollable desire to feel myself inside her juicy, hot cunt.

"Fuck me hard. Come inside. Fill me up," Karen called on me. I relentlessly pounded her instinctively. I felt my balls tighten up. I was ready to explode. I thrust my cock as deep into her cervical opening as far as I could push, shooting my sperm in several plunges.

"Oh my god," Karen sighed when she came down from her orgasm. Kenny was banging Susie from behind as she bent over the foot of the bed.

"I borrowed a bottle of wine from my parents," Karen said as she poured some into four glasses. "Cheers to your day one," Susie toasted. We chatted for a while, and everyone seemed satisfied. I was, and I felt somewhat more confident.

"You should get circumcised, Kenny," Karen said to her boyfriend.

"Yeah, Kenny, girls like Kosher dick," Susie added to the chiding fun.

**********

Jenny didn't have a boyfriend. She dated but never got serious, relishing the romance rather than the rigors of maintaining a steady relationship. Her parents were very conservative, and although she didn't necessarily share their views, she was wary of random, free-wheeling sex. She let Susie know that she wanted sex with Randy on a one-on-one basis, privately.

Susie arranged a hotel room for me after a legitimate date with Jenny. Her aunt Kelli, in her early forties, was Susie's 'more adult' source of alternative behavior. Kelli was relatable to the free-spirited Susie.

"Can you get your parents' car? Kelli needs to register the plate number for your stay," Susie casually demanded from me late Thursday morning, the second day of Hanukkah. I approached my mother and father with some trepidation since it was unusual for me to make such a request.

"I have a date tonight," I explained. "Can I use one of your cars?" I asked my parents.

"Susie has a car. Are you going on a date with somebody else?" my mother asked nosily.

"Well, yes. I have a date with Jenny. I met her in my biology class at school," I told them.

"That's great," my father exclaimed. "Take my Mercedes. Impress the girl," he told me with pride in his voice.

I texted Susie and told her I would be in my father's Mercedes. I hoped the hotel was not in a seedy area of town where it would be stolen. She texted back and assured me Kelli would ensure it was safe for us.

That evening, I picked Jenny up from her home. Her parents questioned me, trying to ascertain my motives, but were impressed that I was well dressed and driving a Mercedes. We went to a nice restaurant for dinner. It was a wonderful evening, and after all my apprehensions, I was comfortable being with Jenny.

Jenny confessed she was not sexually active and had little experience with men, only once before having had intercourse. "I don't know what I was thinking when I offered to do this," she told me after dinner. "Now, I feel safe and comfortable with you."

Susie had given me the room key earlier after her aunt Kelli had checked in. Jenny and I went to the room. I thought the situation should have been awkward, but it wasn't. We kissed. The contact of our bodies was natural and easy.

"We should enjoy the shower," Jenny suggested. I watched her undress. Seeing her perfectly formed, black body made me think of a goddess. We subtly enjoyed each other's bodies as we washed in the warm water. My arousal was evident but not impetuously demanding.

Slowly, we kissed passionately. Our hands caressed each other, touching every accessible area of each other. "We don't need to go all the way if you don't want to," I told her. "This is beautiful as it is," I said sincerely.

"I want to make love to you," she said softly. She guided my hand to her wet, dripping pussy. I inserted a finger gently and began to rub her clit softly. Jenny exploded in a series of orgasms, her body writhing to my touch.

She motioned for me to roll over on my back. Jenny straddled me and easily lowered herself, her hot pussy engulfing my throbbing cock. Steadily, she rocked back and forth and then up and down. I opened my eyes to behold her perfectly formed breasts bouncing up and down to her rhythm.

"Don't come in me," she softly cried as she reached another orgasm. I felt her pussy clenching on my cock, and I felt about ready to come. Gently pushing her off me, she understood and grabbed my shaft, lubricated with her cum, and finished me off.

I called my father, letting him know I would be late, the car was fine, and we were safe. He thanked me for calling and told me to continue having a good time; he wasn't concerned when I got home. I kissed Jenny and held her body close to mine as we lay naked in the bed.

"I will always remember this moment," she told me softly.

"So will I," I responded.

*************

"Randy, I'm not getting good responses for tonight," Susie told me late afternoon on day three. "I can't find any girlfriends who can take care of you."

"It's Okay. I'm fine with the last two nights," I told her. "It was a great idea, but I don't need to get laid every night for the next six days."

"We're going to do this," she insisted.

Later that evening, Susie picked me up and told me she had me lined up for the night. "It's not the greatest, but you need the experience," she said.

"What kind of experience?" I asked.

"I hooked you up with an escort," she told me.

"I don't know if I can do that," I responded to her plan. "It's not safe. I don't know if I'll be able to get it up," I warned her.

Angela, her escort name, advertised herself as a 'spinner.' She was all of four foot nine with unproportionally large breasts, which were most likely implants. She opened the door to the cheap motel room wearing a flimsy robe and invited me in. "You have a nice girlfriend who will do this for you," she said, trying to be friendly and not make it seem as transactional as it was.

"Make yourself comfortable," which I understood meant to get undressed. Angela was methodical. First, sucking my cock, then riding it, and finally having me fuck her doggie style until I came in the condom she provided.

I thanked her as I dressed after a twenty-minute encounter billed as an hour of service. Susie was waiting in her car. "Did you fuck her?" she asked. "Yeah," I replied. "Good, we're on track. Tomorrow will be better, I promise. I have a surprise for you," she told me excitedly.

***********

Susie rang the bell, and my father answered the door. I told him the date with Jenny went well, so he was surprised to see Susie. I told my parents I'd be out late again. They acted a little disappointed that I wasn't going to Temple during the holiday.

"Randy, you know my aunt Kelli," Susie said as I got in the car. I had met her a few times before and knew she had arranged the hotel room for me the night before.

"Yes. And thank you for the hotel room. I had a great time," I told Kelli.

Her husband, Mark, was driving. Susie and I sat in the back seat. Susie had hinted that tonight's activity would be different and exciting. I didn't ask for more information; I was content to be surprised.

"It's a special kind of party," Kelli explained. "Mark and I have an open relationship and like to participate in the lifestyle."

"That means they are swingers," Susie clarified for me.

"We'll introduce you to the couples. There are usually ten or so who come regularly, and since it's the holidays, there might be a few more," Kelli went on. "The first couple of hours, everyone gets to know each other. That's when people decide to pair off privately or in a group."

I was nervous about the folks who would be there, mostly their ages. Mark and Kelli were in their forties. I didn't want to be out of place. "How old are the couples?" I asked.

"Forties and fifties," Mark answered. "Gene and Monica are in their sixties, but you wouldn't know it; they're hot and wild."

We arrived at a large house. Before the introductions, the host couple took us around to show us the rooms where the sex happens. She told me to relax and go with the flow. I wasn't sure I could, so I smiled, hiding my apprehensions.

Two women, Jacqui and Cyndy, took an interest in me. At first, we engaged in small talk, but when I told them I was a business major in college, the conversation turned to financial talk. Jacqui was the CFO of a large corporation, and Cyndy was a bank manager. I sensed their relationship with each other went beyond swinging with their husbands. They expressed their attraction for each other.

Jacqui's body was curvy, her breasts like huge globes. Cyndy was the opposite, petite and athletic. The way they touched me flirtingly had me aroused. I could feel my cock growing in my pants. Jacqui noticed.

"Let's go to a room," Jacqui suggested. Cyndy grabbed my hand, and we went upstairs to one of the bedrooms.

"Kelli had sent the club members an email asking permission to bring a young couple," Cyndy explained while she slipped out of her dress. I was mesmerized by Jacqui's large breasts as they flopped when she took off her bra. "I'm glad everyone agreed," she said, wrapping her fingers around my stiff cock.

Cyndy and I played with Jacqui's huge breasts while Cyndy fingered her. "Ever eat a black pussy?" Jacqui asked me. I had been with Jenny the night before, but we didn't engage in oral sex, so I answered no. Cyndy guided me to Jacqui's wide-open legs. Her pussy was shaved, the dark outer lips glistening with the juices of her arousal. I approached her vagina slowly, as Susie had taught me. First, licking the outer lips before my tongue entered the luscious pink opening.

Jacqui came hard, her strong thighs clenching my head, almost crushing me as my face bathed in her cum. It was so erotic; my cock was throbbing. Cyndy rescued me from Jacqui's grip. She mounted me and took my cock for a ride.

"You can cum in me," she called out, sensing I was about to explode. Cyndy orgasmed with me simultaneously. Lying on my back, my cock held upright despite the release. Jacqui started licking the cum mixture off my penis.

There was a knock on the door. It was Kelli and another man; I remember his name was Brad, but I wasn't sure. "Mind if we share the bed?" Kelli asked. Jacqui pulled her mouth off my cock long enough to invite them in.

Five hot, sweaty bodies bumping and grinding kept me in a constant state of arousal. I fucked Jacqui relentlessly until I was nearly exhausted. Cyndy had left the room and returned with a Margarita pitcher and five glasses.

"I know you're thirsty, but take it easy with that," Kelli warned as I started gulping down the alcoholic beverage. I wasn't used to drinking, so I heeded Kelli's warning and put the glass down. We sat and chatted in bed for a while after being sufficiently satisfied.

*************

On Sunday, day five, I slept until noon, when my mother forced me to get up. "Are you feeling all right?" she inquired, knowing that was unusual for me. "A little tired," I replied, not wanting her to go into a full-blown interrogation as to why I was exhausted.

"Susie's here, downstairs," my mother informed me. I'll tell you'll be down after you shower," she concluded.

I hopped in the car with Susie. She was curious about the night before.

"So, what was it like with the two women? Kelli went to check on you and found you banging the shit out of the black woman," Susie rambled.

"It was good. They got me excited right away, playing with each other," I told her.

"It must have been. Kelli asked me if she could see you alone for some fun," Susie told me. "She thinks you're hot."

"Is that all right with you? And what about her husband?" I asked.

"It's fine with me and Mark told you they had an open marriage. I mean, they fuck a lot of people," Susie responded. "She asked me if you could come by her house tomorrow morning."

"Yeah, that's fine. I like Kelli. She's fun to hang out with. She has a great sense of humor," I told my friend. "Where are we going today?"

"To see my friend, Jasmine. She's into Tantric. She's very spiritual, and she practices spiritual sex," Susie informed me.

"Okay. Sounds like fun," I thought out loud.

The ambiance of the room Jasmine prepared was serene and comforting. Tonal music and the scent of incense lightly filled the air. Pillows covered the floor where the three of us sat after rinsing off with a quick shower. Jasmine explained the body should be cleaned before engaging in a spiritual union.

"Susie is gifting you to me to achieve shared ecstasy. First, we must receive her energy," Jasmine started ritually. "We will begin by giving Susie a Yoni massage."

Susie lay still as Jasmine rubbed her hands lightly all over Susie's naked body. She directed me to caress Susie's vulva slowly and gently. I gazed into Susie's eyes and purposely fingered her according to Jasmine's directions. We brought Susie to a powerful orgasm after fifteen minutes.

The scene with Susie and Jasmine was intoxicating as if I entered another dimension. We sat upright, facing each other, while Jasmine slowly guided my hard cock inside her. Our eyes were locked in a stare into the other's soul. We didn't move. We synchronized our breathing.

Jasmine wrapped her arms around my neck and started rocking back and forth slowly. I had a difficult time resisting the urge just to pound her hard and cum. Time melted away as the energy built slowly.

My hips were still, my cock buried deep inside her. I felt a surge come upon me like a powerful force when I climaxed. We hugged as my sperm flowed into Jasmine. I could feel her vagina clench my cock as if our sex organs welded our bodies together.

Time and space were suspended. Then I returned to earth. Susie's soft-spoken words broke the trance.

"Wow. Did that feel as powerful as it looked?" Susie asked. "Your bodies were shuddering as if you were both going to explode," she told us. It did feel that way.

***********

Kelli was wearing a loose-fitting robe when she opened the door for me late Monday morning. I admired her well-kept, womanly form. She smiled when she noticed I was checking her out from head to toe.

"Care for a cup of coffee?" she asked as she ushered me into the living room.

"Sure. I take it black," I replied. I sat down on the sofa.

"I tried to get Mark into being a naturalist once," Kelli told me when she came into the room with the coffee. "He was opposed to being nude all the time. He's got a nice body. He was afraid of getting his dick sunburned when we went to the nudist resort."

"I can see how that would be a problem," I responded. Kelli had a funny way of coming up with topics. She would think about a story or an incident related to her thinking. I assumed she wanted us to be nude. "I don't think I'll get sunburned inside here," I said while standing up and undressing.

"Be careful not to spill hot coffee on your cock," she laughed when I sat down and grabbed the cup. My cock was only semi-hard sitting there conversing with a naked older woman. She made me feel comfortable.