Date: Fri, 15 Jan 2021 13:13:14 -0700 From: aariel bender Subject: North Cliff Part 18 Ruthie And Her Young Friend North Cliff Part 18 Ruthie And Her Young Friend =====Ruthie Shows The Boys Her Panties====== It's not uncommon for me to stick my head in the door at Ruthie's when I'm in the neighborhood. I wanted to find out about her old friend Cat. "Oh yes, Michele was in and asked me about her too. She wanted to see my modeling pictures. I hadn't looked at those for years. I was pretty back then. I mostly did lingerie modeling, but I did some arty pictures for some of the photographers. Never any porn, just erotic stuff. We were young and it was fun. Funny there should be this sudden interest in my modeling career, I had arranged to do a private show for the son of one of my good customers." "His name is Cary. I noticed when he would come in with his mom, he would touch everything. I even caught him rubbing panties on his face. I quietly told him to not do that. He was a little embarrassed, but was still curious about everything. His mother noticed his touching too. She told me he had been getting into her lingerie drawers. She's been finding cum stains on her clean things. She finally gave him a pair of her panties. She said she understood that boys like girls undies, but he couldn't be using her nice things when he played with himself. She said he seemed happy enough." "He came by the shop alone the other day. I asked him what he wanted. He just said he wanted to look around if it was ok. I told him sure. He confessed that his mother wouldn't let him watch her get dressed anymore. He said when he was younger he was allowed to sit in her room while she got into her bra and panties and nylons. I asked him if he looks at underwear on his computer. He said he did, but it wasn't the same. He couldn't hear the sounds of her getting dressed and the nice smell of her perfume. All the senses. I told him if he could keep a secret, I'd give him a little private show. He thanked me and we made a date for later this week. I was so flattered a young boy would want to see me getting dressed and undressed. Maybe you'd like to join us. He is that age you like. Eleven or twelve. He can shoot jizz. He's cute, with a little button nose and blue eyes. I'm sure he wouldn't mind. I told him he could get naked and jerk off if he wanted. He said he did. I'll give him a pair of my panties as a special gift to help with his wank." "Are you sure he'll be ok with me crashing his party?" "I think it would be good that he knows his little fetish is normal and that even grown men like to touch soft things. You might like my mature figure, it's still as good as it was thirty years ago. Plus I wouldn't mind seeing what it is that attracts all those nice girls and boys. 2.30 on Thursday. Dress nice. That will impress Cary." Well that was an offer I couldn't refuse. I got another offer that evening. Erin called to say a friend of her's and her boyfriend would be in town on the weekend. Nadine is a knock out, I think you'll like her. I don't know her boyfriend, but she usually has good taste in men. A dinner party at my place, then see what develops. You game?" I said I'd be up for meeting her friend. I wasn't sure what to expect. Thursday afternoon couldn't come soon enough. It was a nice day, so I dressed casual. Tee shirt, jeans and slip on shoes. I picked some mommy style panties that I thought might please the boy. Cary was already there when I arrived. Ruthie had told him I was going to join them. He seemed happy to meet me and was excited about the modeling session. Ruthie had told him he could take some pictures if he kept them to himself. He agreed. Ruthie told Marilyn we would be in the party room and not to disturb us. I'd never been in this fitting room. It was smaller than the one we usually visit. There was a couch, mirrors on the walls, In one corner there was a Japanese screen, which Ruthie would duck behind to change, at first anyway. There was also a full bathroom with a large walk in shower. "Cary, Will likes the same things you do. Soft ladies lingerie and the people who wear those nice things. Please relax and enjoy yourself. Pretend you are alone at home doing what you do to pleasure yourself. Everything is allowed here, just follow my instructions. So, like at home, when you are in your room alone, you can take your clothes off. It's more fun to masturbate naked. Please don't rush, we have plenty of time. Watch Will he is an expert at edging." "I don't know how much control you have yet, Just take your time, when you start getting the feeling, slow down or stop. Wait awhile then go easy. If you can keep doing that for an hour or two, you'll have the best orgasm. Let's get undressed." Cary and I undressed, watching each other. Ruthie was watching us both. Cary was in good shape, firm body, tanned, but pale underneath. I was happy to see he was wearing his panties. They must have been from the junior's section. Cute preteen frills. When he got his pants off, he stood facing me for approval. I told him he looked great, even sexy. I took my pants off and did the same, showed him my selection. "Oh wow. Cool. Your dick is already hard. Mine is too. Want to see it?" He pulled those red panties down a little and pulled his nice cut cock out to show me. "Let me see yours" I asked him if he'd help me get my panties off so he could see. I told him I wanted to be naked. He got the hint and took his all the way off and put them on the arm of the couch for later use. Then he got busy with my big lacy panties. I'm sure he hadn't thought about being with another guy today, but he wasn't hesitant at all. He got them off then stood up facing me. He just stared. I was fully hard as he was. I put a hand on his shoulder and let him take it all in. "I've got a boner looking at a dude's boner. That's cool." "Ok boys, I think I'm the star here today. If you guys get started now, I might as well go home." Ruthie told us to take a seat on the couch. I could see the wheels tuning in Cary's head. The realization that maybe there was more options than he had considered before. Ruthie went behind the screen. Her skirt, then her blouse were removed and hung over the screen, so it was clear she was undressing. She came out wearing a classic bra, panties, garter belt, black stocking and high heel. Ruthie is about five foot five. 34D inch bust, strong flat stomach with a nice tapered waist. Beautiful legs too. I'd never thought about what was under her fashionable clothes she wore at the shop. Cary was bug eyed, and had his hand on his pecker. The panties were opaque, and the bra had solid cups.She walked right up in front of us, and turned around slowly so we got a good view of all the details. "Cary, you can touch, so you can see how the different panties feel. He rubbed her ass, very polite, not going right to the magic V. Ruthie put a foot up on my knee and asked if I liked her legs. I put my hand on her calf and enjoyed the texture of her fine nylons. Her crotch was at eye level, which I'm sure she intended. As quickly as she had done that, she turned away and retired behind the screen to change. She tossed the panties and bra to us. I checked the sizes, yes 34B and large. The nylons were draped over the screen. Very sexy. Cary looked at me with wide eyes. I reached over and put my hand on his leg. He instinctively spread his legs. He put a hand on my thigh, then slid it up to my dick. "Can I touch it? I've never seen one so big. Just the other boys at school gym." I nodded. His curious hand gipped the shaft and a finger rubbed the tip. Just then Ruthie came back out. This time wearing a floral set. Bikini panties and a cute bra, not too big. Sort of retro look. She was barefoot now. She danced around the room before turning away from us and bending over. "48 and my ass is still firm." She pulled up the panties so they went in her crack and showed us her shapley ass. No sagging at all. "I see Cary is checking out your tool there Will. That's what you like, a playful young boy. You'll have some time after I'm done to do your boy things." Cary looked at me with an expression of questioning and realization. This routine was repeated four or five more times. The last time, Ruthie slowly peeled out of a see through bra and big black panties. The strip tease was hot. found myself stroking my cock which was oozing now. Cary was seriously beating his meat. I reached over and held his hand and told him to save that cum for me. "Did you ever see inside your mother's pussy?" She didn't wait for an answer, she stood right in front of the boy and pulled her pussy lips apart to show him her clit. Then her foot up on the couch for a better view. Ruthie got on her knees in front of Cary and grabbed his dick. "It's a cute little bit of stick. I think I remember how to do this." With that she went down on him. It was more of a kiss rather than a suck. "Have you ever played with another boy? Sucked his dick." "No this is the first time, with Will. I don't really know what to do." I answered his question by taking Ruthie's place and getting to know his dick better. Ruthie asked where my phone was and started taking pictures. His dick was small, but well proportioned. A little thicker than most boys his age. There was plenty of pre cum to smear around. I loved holding his balls with one hand, and his dick with my thumb and forefinger. Cary was loving my manipulations. "That is even better than when I jerk off." I grabbed his panties off the couch and wrapped them around his dick. The shape of his boner through the panties to my hand was driving me to distraction. I slid the panties down past his cock head and swallowed that purple helmet. "Fuck." The panties moved down to cup his balls and I took his whole dick into my mouth. My tongue licked his ball sack. "Fuck." I wasn't ready for him to cum quite yet. I released his rod. "You want to try that on me? I'd like it if you would." The boy was hypnotized but the visual and tactile stimulation. "Yeah. This is crazy. I never though of doing anything with a guy. I hardly even thought about messing around with a girl. I just thought about rubbing my dick myself." I stood up in front of Cary, dick pointing at his face. He reached up and touched it, then got a good fist grip and pumped me a couple of times. When he saw the bubble of cum starting to drip out, he leaned in and licked it. "Tastes like mine." I sat back down on the couch and told him he could do anything he wanted to me. He surprised me by licking my nipple. Then he took the cue from Ruthie and I, and got between my legs and let his fingers and lips explore. All the while Ruthie was taking photos. She was good, I never noticed. Cary and I were lost in our own play world. "This is so awesome. I want to do this more." His blow job technique wasn't the best, but he was trying to repeat what we'd done to him. I told him when he'd hit the right spots. He knew about cum and knew there would be a load for him. I'm sure he didn't expect there to be that much. The last year had woken my carnal desires for young males. It took some willpower not out looking for boys. My guilt was slightly assuaged knowing that all these encounters were initiated by the boys or others. This feeling was growing stronger in me. Right now all I could think about was Cary's mouth on me. I was very close to cumming. I didn't want to shove my dick down his throat. I let him set the pace. "I'm going to shot soon. Are you going to be ok with my jizz in your mouth? It's going to be more than you shoot." "I'll try. It feels so good in my mouth. I like the taste of my goo. Just let me know." I only lasted about a minute more. And then let loose. "Swallow Cary, now!" He tried. After the first couple of blasts he had to pull off. He caught the most intense pulses in the face. He was slimed. He seemed ok. He was gasping a little and more that surprised to get a hot facial. He wiped it with a finger and tasted it. I licked his face and kissed him. He liked the tongue in his mouth and returned the favor. "I forgot how hot watching two guys could be. Some of the male models would put on a show for us girls. But I've never seen a boy with a man. I don't let my little gatherings have their sex here." "Ok Cary, I want to make you feel good. Sit down again." He could hardly contain his enthusiasm. "Are we queers? I just sucked a guy's dick and liked it." "No Cary we are just two happy boys who know how to have some fun. Sit back and enjoy." Ruthie was sitting on a chair across from us. Leg spread and a finger on her love button. "God Will you look so good with that boy. Make him cum hard." I intended to blow his little mind. I got my hand under his small ass and started playing with his asshole. He grunted and pushed down on my finger. It went right in. He was tight. I just let him get used to the idea of anal penetration while I pleasured his cocklette. He was actually well hung for a boy. Plenty of girth to suck on. I was stroking him with my finger and thumb. I was pushing hard with my thumb on the base of his rod. "I'm getting the feeling." A small glob of liquid confirmed he was close. I increased the suction on him with more tongue action. "Ummm. Ahhhh. Urrrggg." I got a nice load, Sweet. It went down in one gulp. I didn't stop yet. I stayed on him until I felt him starting to wilt in my mouth. I still had a finger in his ass. Now I could focus on that end. I told him to get on his knees on the floor. "You're not going to fuck that darling boy are you?" "What do you think Cary, something bigger than a finger in your ass?"" "Your dick? Try it." Ruthie handed me her bottle of lube and I prepared the boy's ass. I was burning with desire now and only had a little bit of mercy. I wasn't going to hurt him. I was just going to test his resolve. "I'm just going to put it in a little tell me if it's ok. I'll stop if you want." The tip of my dick made it past his last line of defense. "Ok, it's ok. Just wait a little." Good enough. I counted to ten and pushed in a little more. "It feels huge. Just wait again." Another count and another inch in. I stopped there. I could feel him adjusting to the intrusion. "It's bigger than mom's toy. It feels way better. I can take it all in now." Ah, he has done his own ass himself. That eased my mind some. Ruthie was transfixed. "I'm going to move in and out now, I'll be gentle. I'm going to cum in your ass. Mom's toy doesn't do that, does it? I closed my eyes and had at it. Cary hummed and grunted quietly as I fucked him. I checked, he was half hard. I could hold his dick balls in my palm. As I pumped his ass, I could feel it coming back up. I squeeze the shaft and got another small drop of pre cum. I caught it and brought it to my mouth. That taste fueled my illicit desire. The faster I slid in and out, the harder Cary got. I must have hit his prostate just right. I got a handful of cum and he let out a gasp. I kept pumping but I wasn't meant to last much longer. He gasped again when he felt his ass flooded with hot jizz. I slowly removed myself and Cary laid down on the floor. I looked over to Ruthie who was still sitting. The look on her face. Her pussy was wet from her masturbation session which was focused on my romp with the boy. Ruthie is quite beautiful. And sexy. I moved over to her. I put my hands on her spread knees. "Oh Will, you know I prefer women. It's been too long since I even shared this with anyone. I don't know if I can try again now." "You don't want to be left out. Please make an exception for me today." I kissed her knees, then her thigh. She put her hands on my head. I assumed she was going to push me away. She didn't. She closed her eyes and pulled me close to her soaking snatch. I took that as invitation. I wasn't going to change her mind about me, but a it's just a tongue on her pussy. It has no gender. Ruthie wrapped her legs around me neck. "Make it good Will." I hope Cary was watching, but I couldn't turn to see. Ruthie was steamy. Her scent was slightly musky. The taste was tangy and sweet. Her lips and clitoris were fully engorged with blood. Spread and firm. The first touch cased her to shake. " "Yes, I remember that feeling now. Please don't stop until I tell you." I didn't consider this a conquest of a lesbian woman, it was just sex for pleasure. After watching Cary and I, Don't know how she saw me now. She's always known about that part of me. She offered the boy to me just for one reason only. Now Ruthie was using me, or maybe allowing me to pleasure her. I don't know how long it had been since she had sex with another. She wasn't hesitant. Ruthie was in her late forties. That would make her the oldest woman I've been with. The only difference between her and a younger woman was that she was much more responsive. It wasn't frantic, it was well paced. As we progressed she became more aroused. Her vagina lips parted and allowed me to push my tongue deep in. Her clit was a little larger than average. I could get a firm grip on it with my lips. I must have licked her for twenty minutes when she started to meow and growl. Years with out the touch from someone else is unimaginable to me. It was not longer tolerable for Ruthie. Her hips started moving and she pushed hard against my mouth. I knew she was close to orgasm. I was determined to make sure she reached the magic plateau. I slipped a finger inside of her. That did it. I could feel muscles clamping on my finger. Her legs squeezed me with some real force. Then a long moan. She held on for a little more, then went limp. Cary had been looking over my shoulder. He moved up next to me to get a better look. "You ever seen your mother naked? A girl up close. Ruthie is the real deal. This little party here today is why I like boys as much as women. The best of both worlds as they say. Let's get you cleaned up. Are you going to need a ride home." "Thanks. All that jizz is leaking out of me. I can walk home we live just a couple of blocks away in the Atlas building. Mom has a whole floor. It's pretty nice. Is Ruthie ok?" "I'm ok. It's just been a long time. Will knows what he's doing. I guess you know very well. Please don't tell anyone about this. If word gets out, half of my customers, women and men will be asking me out. I like my privacy and solitude." Cary made his way out, leaving Ruthie and I naked and glowing. "He's another single parent kid. So many of them are these days. His parents were a power couple in the tech scene here. He was just too fixated on money for Jill, Cary's mom. He moved out to the coast to work for Google. She got a massive payout. Her condo at the Atlas is amazing. I think she moved there just to spite her ex." The Atlas was one of the older downtown building It was the tallest in town at the time. The top six floors are condos, Jill's might be the only the that is a whole floor. The building was beautiful, marble and glass. I'm sure it's had some updates, but my guess is the space is much like it was when it was built in the early 20s. If Jill is still working, I suspect Cary has lots of time to get into her things. I must follow up with him. "Thank you Will, I realize I'm not afraid to let someone get close to me anymore. I can't promise you a return engagement, but I think that was a fair trade. You were so good with that boy. He didn't leave feeling taken advantage of. He just confirmed his deep desires. I think I should get him some more feminine outfits. He would make a lovely girl." Meeting Erin's friend, Telly and her guy Steve was not a success. Telly was good looking, funny and bright. Her Steve was nice enough, a little too loud and his jokes were never funny, mostly mean. Dinner was fine. The others decided to smoke some pot for dessert. I don't care for that and stayed with the wine. After a while I noticed that Erin and Telly had disappeared leaving us guys alone. "Well, dude, since it's just us boys now, how about we see what we can get up to. Erin told us you are pretty open minded and wouldn't be offended by the suggestion we tend to a man's needs. Let's go to the guest room and see what we can come up with." Since I wasn't going to get any of the guest pussy anytime soon, I agreed, despite my best instincts. "We'll need to undress. I'm dying to see what you are packing. Erin says you are quite the stud." Steve wasn't half bad looking and was sporting nice wood as soon as he was naked. Then he got a little squirrelly. He hesitated, so I reached out to give his pole a tug. Big mistake, He fired off his load as soon as I touched him. "God damn it. Fuck it all. Why does that happen on first dates? Fuck. Telly is patient, but I know she thinks I'm a loser who can't hold his fire. Aw fuck it fuck it." He slumped down in a chair holding his head mumbling about how he rarely get's a second date with anyone. I could see this was not good and backed off, got dressed and let myself out. Later that evening, I got a text from Erin asking where we were. She said Steve and his suitcase were gone. She thought we might have come back to North Cliff. I told her what happened. She must have told Telly because she said I was smart to leave. Steve can get violent when this happens. Erin called the next day to say that Telly had left too. She sent Steve a text letting him know she wouldn't be seeing him again. And for him not to call ever again. "Sorry Will. She a good friend. This was poor judgment on her part to bring him with her. The three of us could have had some fun. I'll make it up to you. Please don't let this damage our friendship." I told Erin not to worry. I just went home and jerked off for a couple of hours. I didn't want to bother Michele. It would seem rude to ask her to be my second choice for the night. I told her about it. She was thankful I was careful and got out as quick as I could. A lesson learned. There will be another day.