Chapter 51

More New Year celebrations.

It was a good thing I had set my alarm before going to the party the evening before as I had promised to visit my oldest lover Alicia at 3 pm. This was extremely important as she had lost her son, my former school friend in the past year, and was still grieving, not to mention that Alicia had been like a second mother to me for a big part of my life.

I quickly shaved my face, well that part that needed shaving as I still sported a goatee I’d had since I was about 20, then I jumped in the shower. The rest of the shaving was done under the shower. With just a dash of aftershave and some deodorant, I was smelling like roses and ready to roll. Right on the dot of 3, I rang Alicia’s doorbell. The door was opened by Gladys, her daughter-in-law.

The last time I saw Gladys was at the beginning of the previous year, at her husband George’s funeral. George was Alicia’s son and my old school friend. She was a big woman and she looked great. During our school days she was one of the most beautiful girls there and I, together with about half of the male school population, had a crush on her but she only had eyes for George. She was two years younger than we were, so that would make her around 58 now. They got married when George turned 20 and Gladys was 18. It took an awfully long time for them to have a daughter. Gladys had several miscarriages before it finally happened when she was 40, I wondered if her daughter Ariel would be there as well.

Gladys was a force to be reckoned with, she ran a chain of haberdashery shops in the major shopping centers in the country. She and George started the business together, but after a few years they figured out he was not cut out for the business world and became a house husband. When needed he worked in the shops when the local manager was ill or went on vacation but that was about the extent of his involvement. For the rest, he took care of the household, made sure there was a hot meal on the table when Gladys came home from work, and later he took care of their daughter Ariel as well. So it was a big blow for Gladys when the love of her life passed on.

“Come in Lew, welcome.”

“Hello Gladys, Happy New Year!” I said to her giving her 3 kisses on the cheeks as is the custom in our country. When I came into the living room Alicia held her arms open wide and wished me a Happy New Year as well. Next to her stood her granddaughter Ariel also with a big smile on her face, waiting to give me a hug and the traditional kisses, while also wishing me all the best for the coming year.

“Wow, that’s a welcome I wasn’t expecting, three of my favorite and most beautiful women, I’m overwhelmed.”

Alicia looked at me with a mischievous smile on her face, “I bet you kissed a lot of pretty ladies a little more than 12 hours ago at your New Year’s party. I turned a bit red and had to admit that I had had my fair share of New Year’s wishes at the party.

“But tell me how are you doing? And to what do I owe the pleasure of seeing Gladys and Ariel?”

“I’m doing fine, 78 now, but of course, you remember that, as you turned 60 and we differ by 18 years.”

“How could I forget, you turned me into a man when I was 18, and you were twice my age, luckily you’re no longer twice my age, else you’d be 120 years old.”

“God forbid, I never want to be that old, even if it were humanly possible.”

“I’m sure if you get that old you’ll still look like you do today.”

“You can’t stop flattering the ladies can you?”

“That’s one of the many things you taught me, Alicia.”

“And you were such an eager pupil.”

“Yes I was and I’m still capable of fulfilling the toughest assignment you ever gave me.”

“Are you referring to the 10-to-1 challenge?”

“Yes, I am.”

“And you still can do that?”

“I haven’t tried to do it recently, but I have tried to keep from, you know what, for more than 20 minutes and won a couple of bets that way.”

“You’ve got to tell me more, but first let’s have some tea and cake while you enlighten me about this wonderful purpose in life you’ve found your photoshop and studio.”

During the tea and the cake we had, I told Alicia, Gladys, and Ariel about my adventures in the photo studio, careful not to actively broach the subject of sex. After a few minutes, Alicia stopped me.

“Listen, darling, Ariel is eighteen, she knows all about the birds and the bees, so you don’t have to beat about the bush when you talk about fucking and sucking, and although she’s still a virgin, she knows everything there is to know about what naughty boys, like you and innocent, but eager, little girls like her are up to.”

“I’m sorry but I had no idea how far you had taken her with her sex education.”

Ariel, slightly flushed, added, “Granny’s right, I know all there is to know about boys and girls, but like you were, at the age I am now, I’m still a virgin. Maybe I should find a person twice my age like you did at the time to remedy that.”

“You know about that too?”

“Yes, Granny told me everything about you, also about the 10-to-1 challenge she gave you?”

“Oh my God, you’ve really been fully educated on the subject of sex.”

“Yes and while we’re on that subject, I would like to mention that it’s been more than 9 months since my mother had sex.”

“Ariel! What are you saying!” Gladys shouted.

“It’s true mommy, you haven’t had any real pleasure since daddy died, I’ve heard you use your vibrator at night when you think I’m asleep, so I know you have needs, just like me by the way, and I discussed it with Granny to see what we can do about it.”

“You told Granny about this?”

“Yes and she thinks it’s high time we found you, someone, to relieve the pressure.”

“Oh my God, my daughter wants me to have sex with a man to relieve the pressure.”

“Yes, mommy and you’ve really been on edge now for the past 3 months. So any volunteers to take that pressure away?” Ariel said looking straight at me.

“Ariel, it’s not because Lew had sex with me in the past that he wants to play with your mother,” Alicia said.

“Play? You mean fuck my mother, Granny?”

“Ariel that is no way to talk!” Gladys interjected, “I want you to apologize immediately to your grandmother and Lew!”

“Now, now, Gladys, there is no need for that,” I said, “It’s clear that the poor girl has your best interests at heart; she feels that you are suffering and she knows about my history with her grandmother, so it’s only a logical conclusion for her, also knowing I’m unattached, to assume I would like to have sex with a younger beautiful needy woman like yourself.”

“Yes but to say it out loud.”

“If you don’t want to mommy, I wouldn’t mind if Lew would deflower me.”

“WHAT!” I responded totally taken by surprise, “NO way am I taking your virginity young lady, for that it would be far better for you to find a man much closer to your own age.”

“Not according to what I’ve heard from my friends, their defloration with a guy their age was a total disaster, they advised me to never do that.”

To be honest I wasn’t liking the way this conversation was going and it got worse when all of a sudden Ariel lifted her sweater and showed her boobs to me.

“What do you think Lew, are my tits as nice as Granny’s?” I tried to look away.

“Stop that, young lady, you’re embarrassing our guest,” Gladys said.

“No, I’m not, besides I want an expert’s opinion.”

I looked Ariel straight into her eyes, avoiding her gorgeous teenage boobs, “What makes you think I’m an expert?”

“You’ve photographed dozens of women in the nude, so that makes you an expert in my books.”

“OK, I admit I’ve seen my fair share of boobs but does that make me an expert?”

“Maybe you not only need to see, but maybe you need to feel as well...” she said, grabbing my hand and putting it on one of her tits. It felt marvelous, soft, and yet so firm, I couldn’t help a guess, “a C-cup like your grandmother?”

“Yes, squeeze Lew and tell me...” she looked expectantly at me.

Slightly turning red in the face I had to admit her boobs were fabulous, I even ventured to tell her they felt exactly like her grandmother’s when I was allowed to touch them for the first time so many years ago.

Without hesitation, she took my other hand and put it on the twin. When I slid my thumb, involuntarily, over the nipple I felt it harden. This young lady was clearly aroused, and I began to wonder where this would lead. I didn’t need to wait very long to find out. With both her hands now free she grabbed her mother’s sweater and pulled it also up revealing her bra-encased tits.

“What are you doing?” Gladys shouted.

“Come on ma, you’d love to feel Lew’s hands on yours as well.”

“Maybe but would Lew like that too?” she said in response looking at me instead of her daughter.

“Yeah, why don’t you have Lew check out your fun bags as well Gladys?” Alicia said, “take off your bra, you know what, I’ll take mine off as well,” after which Alicia pulled her sweater over her head and undid the clasp of her bra setting her boobs free.

I was now looking at two pairs of almost identical tits and one seemingly bigger pair still covered by a lace bra, Gladys hesitated.

“Go on!” both Alicia and Ariel said in unison.

That did it, Gladys pulled her sweater over her head and unclasped her bra, finally setting the third pair of boobs in front of my face free. By then I had let go of Ariel’s so she immediately grabbed my hands again and put them on her mother’s tits.

“Now feel hers,” she commanded. When I cupped Gladys’ mammaries I let my thumbs slide over her nipps also feeling them stiffen at my touch. What have I gotten myself into? 3 hot females one of whom was still a virgin, and seemingly very eager to change that status.

“Well, what do you think?” asked Ariel.

“Mhmm, nice, bigger than yours I must admit.

“Yes I’ve got a D,” Gladys said a bit proudly.

“I guessed you had dear,” I responded.

“You see now Mom, I told you he’s an expert.”

All three of them were now looking rather eagerly at me, I guess waiting to see who would dare to do something about this situation. Again I didn’t need to wait very long to find out. Ariel was clearly the head of the line. She stood up and began to undo the button of her jeans and slide the zipper down.

“What are you doing?” her mother asked.

“If he’s an expert on boobs, I’m sure he’s an expert on pussies as well, so I’m getting his opinion on mine,” she said stepping out of her jeans and sliding her panties down. She now stood completely naked in front of me, her cunt barely inches away from my face.

“Well, what do you think?”

“You have a nice bush,” I ventured.

When she saw I wasn’t moving or doing something she again grabbed one of my hands and put it on her cunt. Her ample bush felt silky soft to the touch, she sighed and looked me straight in the eyes, and very boldly asked me, “Would you like a taste?”

“Ariel, your manners!” her mother said. I saw Alicia chuckle, she clearly knew her granddaughter much better than her mother did.

“What? Men like to taste pussy and I want to know if mine tastes good, I can’t taste it myself can I?”

“If you must know yes you can,” Gladys ventured.

“How?”

“Have you never tasted your fingers when you were masturbating? And don’t tell me you never masturbate, I know you do it regularly.”

“Of course I have, but how can I know if it tastes good, I’ve got nothing to compare it with.”

“Yes, you’re right, you’ve never experimented with girlfriends?”

“No, have you?”

Gladys turned beet red and hesitated to answer...”Euh ... yes, before I met your dad.”

“You mean when you were my age?”

“Yes, a little before even.”

“Wow, my mom was a lesbo when she was a teenager!”

“NO! I was not a lesbian, I merely experimented with my best friend, don’t forget in those days we were not as liberated as you are now.”

“Granny was and she’s 20 years older than you are.”

“She’s got you there Gladys,” Alicia chuckled.

“OK, yes I had a girlfriend for a few years before your dad and we had sex, lots of it, but it was your dad who took my virginity.”

“And how was it?”

“Not really what I expected it to be, we were both very inexperienced.”

“That’s why I want the man who will deflower me to know what he needs to do and make it an unforgettable, wonderful experience for me, after all, it will only happen once in my life.”

“She’s right again there Gladys, it is indeed a once-in-a-lifetime experience, isn’t it Lew?” Alicia replied looking straight at me.

“Euh ... yes it is, and I will always be in your debt for taking me on that adventure.”

“Care to pay back that debt Lew?”

“What do you mean Alicia,” I replied, not wanting to admit it but, immediately understanding where she was going with this.

“You know what I mean clever boy ... I shook no with my head but she knew from my body language I understood what she wanted me to do.

Taking the cow by the horns so to speak, Alicia continued, “OK let’s make this simple we all know where we want to go with this, shall I direct this movie?”

“Yes!” both daughter-in-law and granddaughter replied in unison.

“Good, you Gladys, take off the rest of your clothes so we can get Lew at the right temperature.

“Don’t I have any say in this?” I token protested.

“NO!” all three replied in unison.

“While your mom gets undressed, you undress Lew Ariel. Get up, Lew!”

What could I do, I was completely outnumbered so I stood up and allowed Ariel to undress me. When she finally pulled my boxers down, my cock sprang out, rock hard of course. Not surprising after the boob show and seeing the woman I had had a crush on during my teen years plus her gorgeous daughter completely naked; the mother with a body many a man would still drool over and the daughter who could give many a youngster wet dreams. Gladys took my cock in her hand, guided me to the bedroom, halted me at the foot of the bed with my back to it, and gave me a push so I fell flat on my back, my cock sticking up like a flagpole. Next, both mother and daughter climbed on the bed and Gladys began licking my dick almost like giving a demonstration to her daughter on how to perform the perfect fellatio.

Ariel was an eager pupil, quickly taking over from her mom taking me all the way down into her throat surprisingly without gagging. She may be a virgin, but I wondered if this was really the first time she had a cock in her mouth. She knew exactly where to find the sensitive spots licking around the rim of the head tickling the underside and when she took me all the way in, the little minx even managed to lick my balls that way with her eager little tongue. By the time she had finished, my cock was almost ready to explode but looking at Alicia, who was standing next to the bed I managed to keep from cuming. Maybe I should try to have sex with Gladys first before I tackled Ariel’s virginity.

“How about a little warm-up girls?”

“I thought that was what we were doing,” Gladys replied.

“In a way, yes, but taking a girl’s virginity is very arousing and I wouldn’t want to cum too soon so maybe I can have some sort of a dry run with you?”

“Who, me?”

“Yes you Gladys, you know I had a crush on you when we were young.”

“No, I didn’t, is that why you had sex with Alicia?”

“No,” Alicia interjected, “we had sex because he couldn’t get any other girls because he was too shy.”

“Yes I remember, he was part of the nerd gang, wasn’t he?”

“Yes, I was Gladys and I’m not proud of it, and you were the hottest girl in school.”

“No, I wasn’t, where did you get that idea?”

“You must have been aware that all the boys wanted to get into your panties, but you had only eyes for George, we were all very jealous. So what about you make my teenage dream come true and have sex with me? Based on what I heard your daughter say, you need it.”

“Yes, it’s been a long time since I last felt a man’s body on top of mine with his cock inside.”

“I’ll make it easy for you, why don’t you get on top?”

“Can I? That has always been my favorite position.”

“Yes you can, and while we’re at it, why don’t you sit on my face Alicia, that way Ariel can learn a thing or two about having sex with multiple partners at the same time.”

“Do you really want to lick my old pussy?”

“I loved your pussy when I was young darling and I still do now, so climb aboard ladies, let’s get this show on the road.”

Gladys got on the bed, straddled me, and maneuvered her pussy right above my cock which still pointed to the ceiling. She took hold of it and rubbed the head between her inner lips, lubricating it with her juices. When she thought it was slippery enough she slowly impaled herself on my dick. It was pure bliss to see, first, the head and then the rest of my rigid pole disappear inch by glorious inch into her hot body.

Even now, so many years later she made my heart beat double in speed. This was something I had fantasized about for many teenage years while I masturbated alone in my bed at night. When she then began to move up and down, actually fucking me her boobs danced on their own, I was mesmerized, looking at them move, but not for long. Alicia, also rather eager to have her cunt licked had moved to the top of the bed swung her leg over my head, facing me, and lowered her already moist pussy over my eager mouth. I went to town on these, for me, oh-so-familiar pussy lips. When after a few minutes of licking and sucking she began to flow, I immediately recognized her sweet taste. This was really a trip down memory lane, well it had been every time I had the pleasure of having sex with her over the many years that we knew each other. Only this time it had been quite a while since I last had the pleasure of tasting her.

Both girls began, almost simultaneously, to moan. It sounded better than the best choir I had ever heard. From the corner of my eye, I could see Ariel standing beside the bed vigorously fingering herself. I grabbed Alicia’s butt and pushed her a bit up, so I could get to her little brown star. After a bit of fumbling, I couldn’t see where I was going, I managed however to stick a finger in her vagina and began fingering her as well. My ultimate goal was to pick up enough lubricant to be able to stick a finger in her butthole. She never liked me to fuck her backdoor but she loved to have me stick a finger in there. I wondered if Gladys would like to be ass-fucked. Something I definitely wanted to find out this afternoon.

When I deemed my finger well lubricated I ventured to find Alicia’s backdoor, again difficult without being able to see where I was going, but if I went down over her perineum I was bound to find it, and yes I did. When I pushed lightly she moaned. I was able to peer over her still flat tummy between the valley of her perky boobs to look into her eyes. She had been looking down all the time, so our eyes locked and she gave me a look of approval to continue my invasion of her asshole with my lubricated finger.

I pushed a bit harder and heard her take a deep breath as the top of my finger slipped in. I began wiggling it about and pushed in further. Alicia came and she came hard, her breathing increasing in speed, moaning and groaning at the top of her voice. I saw her stomach go in and out, just the same as it had so many years ago when I made her cum for the very first time.

In the meantime, Gladys had been riding my cock, going up and down and gyrating her hips, a pending orgasm slowly building up inside her. With Alicia still on top of me, I couldn’t see her, I could only feel her pussy muscles working my cock and hear the mousy little squeaks she made, every time she slid down.

Alicia got up and moved away so I could now fully concentrate on Gladys and again feast my eyes on her gorgeous body on top of me. I enjoyed the view for a few more minutes before I put my hands under her butt and lifted her up.

“Time for a change,” I said while I rolled her to the side of the bed on her stomach. I then pulled her up with my hands at her hips onto all fours. She quickly grasped where I was going with this and assumed the position, impeccably sticking her bum out. What she didn’t know was that I had every intention of entering her back door rather than her front door. To facilitate my move I stuck a couple of fingers in her dripping pussy and gathered up as much juice as I could and smeared it all over her pucker; when I also spit on it she got the picture. She raised her upper body making it impossible for me to proceed.

“I’m not so sure I like where this is going, Lew.”

“What do you think I was going to do?” I replied looking all innocent.

“I have the feeling that you intend to fuck me in my ass.”

“Do you have a problem with that?”

“Well, I’m very like my daughter when it comes to that body cavity.”

“Are you telling me you are an anal virgin?”

“Yes.”

“Would you like me to change that for you?”

“I’m not so sure.”

“You want me to take your daughter’s virginity but you’re not willing to offer up your own?”

“That is entirely different.”

“No mom, I think Lew’s got a point.”

“You mean that I should allow him to take my anal virginity if I want him to take yours?”

“Yes, I think that’s only fair, I shouldn’t be the only one to give up something I can only do once in my life.”

“I’m still not so sure about it.”

“OK, if you’re not willing to do that I’ll go out on the street naked and have the first man I meet take my virginity instead of Lew.”

“You absolutely won’t young lady.”

“The choice is yours’ mom.”

“I never let your dad assfuck me and I’m too old for such foolishness now.”

“You always taught me a person is never too old for a new adventure Mom.”

After a long time, Gladys finally agreed to make this ultimate sacrifice for her daughter.