Learning about jacking off Part 29

Just a note: I have written two Part 27's to this series because I fucked up. You should read "Learning About Jacking Off Part 27 Rachel's T" in order to have continuity with this one. If you haven't read any of those stories you might do well by starting with "Learning About Jacking Off Part 1" Thank you. The driver smiled at me as I got off the bus. I smiled back at her and walked casually down the steps. I stayed a good hundred feet behind the old woman. In her black dress and black shoes she reminded me of a witch in the cartoons. The woman seemed to know I was thinking about her. She stopped and turned around and gestured me forward. "My daughter lives in that yellow house there." She pointed to a house three houses away. "I will go in the front door. YOU will go down the alley in back and wait for me by the large tree just inside her gate." I nodded my head and said, "My fee is $100 for specialty visits." It wasn't, but I thought she would be desperate enough to pay it. The old woman snorted and said, "You'll get fifty just for coming into the room and fucking me. I'll give you another fifty if you make me cum." She leaned forward and said, "I'm a screamer when I come. I also squirt...or at least I did once when I uh had sex with someone who really cares for me." I nodded my head and said I would wait by the tree. I found the alley and soon enough found the tree behind the yellow house. I slipped my hand inside my underwear and ran it over my semi-hard cock. I pulled my hand out and sniffed it. The smell of cunt was almost negligible. I couldn't smell more than the slightest hint of it. I wondered how the woman had been able to smell it so far from me as she walked into the bus. I had been standing there about fifteen minutes when the back door opened and the old woman beckoned me into the house. We stepped into a mud room. The woman moved next to me and in a none too silent voice said, "My daughter is in the living room. She knows I have a gentleman friend. She knows that you are here for sex with me. Don't be surprised if she opens the door and comes into the room while we are engaged in what I am paying you for. She is, however, a bit shy so we will arrange something else. I thought about asking her daughter to just come in and have a comfortable seat...but decided this is what they had worked out and that would be enough. She opened the door to the rest of the house and I followed her as we walked down a short hall. She opened the door and walked in. She stood by a queen-sized bed, opened her arms and said, "Kiss me whore." Smiling at that I walked up to her and kissed her like I kissed Ellen from next door. My lips were moist, hers weren't so I used my tongue to wet her lips then rubbed my lips lightly against hers, barely touching them. The woman shuddered, pulled back from my face and said, "For someone your age you have some talent." I put my hands on her shoulders, pulled her face down to mine and we both kissed open-eyed, my tongue moving over hers and my lips sucking hers into my mouth. I put a hand to her dress and found a hard nipple. I pinched it just hard enough that she moaned into my mouth. She pushed me away panting and said, "Take off all of your clothes!" She sat on the bed and watched me pull off my Batman tee shirt. I knelt to the floor to untie my red converse sneakers and pull them off followed by my socks. I stood back up, the old woman's eyes riveted on my cut-off shorts. I unbuttoned them slowly, then dropped them to the floor. Now in just my underwear I asked if she would like to take them off. She grinned wickedly and said, "Just what I wanted to do sonny." She moved from the bed to her knees. I watched her wrinkled hands move to the elastic of my underwear. Her nails were long and they sc****d the flesh right at the elastic as she pulled them down. Her eyes looked at my cock like she had just discovered gold and diamonds. She put her hand around the base of my cock and said, "I thought your cock was nice on the bus, but seeing all of you naked I am going to love this fuck." She patted my balls, feeling each one, rolling it between her fingers before moving to the other. I was very very hard. I asked, "May I undress you ma'am?" She snorted and said, "My name is Ruthie. Strip me naked sonny." She stood up and turned her back to me. I unzipped her black dress. She was wearing no bra. Her tits sagged, but her nipples were glorious. They were hard and red and stuck out like little thumbs. I knelt on the floor and removed her shoes and stockings. She had long black stockings that hooked with a garter at the top of her thighs. I could smell her cunt already as I undid the garters and pulled the stockings down. I hooked my fingers in the elastic of her black panties and looked up at her, my eyebrows raised in question. "Yeah, fuck yeah, Pull down my panties sonny. I am so fucking wet right now. It's been a dozen years since the last time I was fucked. I had to pay for that one too. She laughed in a cackling sort of way. Her cunt hair was full, mostly black, but some gray and white hairs there too. The bush held her cunt scent which was awesome. I pushed her back on the bed and spread her thighs to lick her cunt. She stopped me. "My daughter's name is Clarice. She is in the living room. She isn't expecting this, but I want you to go into the living room, introduce yourself, then invite her to come with you to my room. I was surprised by this, but it was kind of exciting to meet someone when I was totally naked and very much ready for action. I smiled at Ruthie, opened the door and walked down the hall to the opening that lead to the kitchen. The living room was just beyond that in the next room. I heard a soap opera on the television. I walked into the living room. Ruthie's daughter Clarice was watching the television intently. I moved closer to her and she still hadn't noticed me. So I walked between her and the television. She shrieked, her eyes wide open. Clarice stared openly at my hard cock for several long minutes while she tried to calm down. Finally she looked up at my face and in an agonizing whisper voice said, "Mother said you were young. I had NO idea how young. How old are you anyway?" I told her and she shrieked again then clapped her hands together. "My Lord you are beautiful. Have you fucked Mother already?" I moved closer to her, now only several feet in front of her. She stared at my cock intently then looked up at my face. "I haven't fucked Ruthie yet. She thought you might want to watch us fuck." Clarice's hand went to her mouth. She had to be 40 or so yet seemed younger than that with her reactions to me. But then how would any woman react to a person like me walking naked into her living room? "Would...would that be all right with you?" Smiling I told her I liked to keep the customer happy. She did a double take at that then said, "Oh yeah. Mother said you were a professional." She took a deep breath then said, "Yes I DO want to watch. Mother...did she tell you about me?" I shook my head no and said, "She only told me this was your house and that you might want to come in and watch. I thought you were coming in later, but now is fine with me." As we walked down the hall she asked me again how old I was. I told her again. She gasped again. When we got to Ruthie's room there was a chair right next to the bed. Ruthie patted the chair and said, "Right here honey. This young man is going to pleasure me and if he does it right he will make $100. That's little enough to pay for what I need." Ruthie dutifully sat down on the chair. She was wearing a dress that more closely reflected the season. It was a bright yellow sundress. She had nice sized breasts without being too big. Her nipples were very evident under the thin material. I climbed onto the bed and, with my knees right at Ruthie's cunt I leaned forward and kissed her gently at first then turned up the heat. My hands squeezed her breasts, lifting them and letting them down as my fingers pinched her nipples just enough. Now our tongues were in active battle with each other. Even up here I could smell her cunt. I was looking forward to getting my face onto and into that. Ruthie sat on the chair primly. It was much like the look she had when she was watching the soap opera. There was a bit more color in her face though. I moved my face from Ruthie's face. My hands grasped her droopy tits, squeezing them so they almost seemed ready to burst. It was like squeezing balloons that were inflated for several days and making them look almost like that had looked before. Her nipples were huge and turgid. I opened my mouth and with my teeth, clamped tightly onto the base of the left nipple just above the areola. My tongue moved over her nip inside the cage my teeth made around it. Then I pulled my head back, opened my mouth wide and pounced upon her nipple like I was going to bite it off. I landed on it with my lips though and sucked her hard. I pulled back on the nipple, the suction from my lips pulling it up a seemingly impossible amount. Ruthie gasped and croaked out, "I think you are going to earn your money sonny." I released her nipple letting it fall back down onto her saggy tit. From the corner of my eyes I saw that Clarice was at her face rubbing her finger lightly over her lips. She licked her finger and used the lubrication to work lightly over those red lips so they were swollen. I pressed Ruthie's tits together and placed her nipples next to each other. I sucked them both, my tongue moving between them as Ruthie moaned and then howled. I leaned back and said, "Hold your thighs up and apart Ruthie." She did as asked. I held up my hand, the middle two fingers raised up. The old woman grinned at that. I used the fingers on my left hand to spread her hairy cunt lips wide open. Ruthie and Clarice were both looking down where she was opened up. The curtain of black hair made the red sodden insides of her more dramatic. I pushed my fingers over to Clarice who leaned back startled. "Clarice, would you mind sucking on my two fingers here. I would like them to be very very wet before I push them into your mother's cunt. She had a finger still caressing her lips, stopped and considered my request. She grasped my wrist and sucked on my fingers like they were a cock. Her other hand was inside the bodice of her dress obviously playing with the hard nipple that was just hidden underneath. She licked between the two fingers obviously enjoying herself. When I pulled them from her mouth she had a disappointed look followed by the fascinated look she gave as I plunged the fingers into her mother's cunt. Ruthie gasped as they bottomed out into her. She pushed her thighs together then and rubbed her thigh against each other which caused her cunt to clamp tight on my fingers. Ruthie was moaning louder now. I sort of punched the fingers back and forth hard into her while they fucked her. The smell of cunt was very evident in the room. I wondered how much of the scent came from Clarice. "Oh my FUCK Peter. Press your fingers up against the roof of my cunt...don't stop! Press hard, pulsing them up there!" I did as she asked, my fingers almost aching I knew not to stop. Ruthie's head was back, her neck pushed forward as she ground the top of her head into her pillow. A long almost fire-hose like blast of clear liquid shot from her cunt around my fingers, some of it hitting my chest, a bit of it splashing onto Clarice's sun dress. I kept the upward pressure going as long and a bit longer than she was squirting. I had never witnessed anything like this before. At first I thought it was pee, but it was clear and smelled nothing like urine. Finally Ruthie put her hand on my wrist and pulled the fingers slowly from her cunt. I pulled the fingers up to my nose and sniffed the strong scent of cunt. I smiled at her then at Clarice. Clarice's face was red. She reached slowly but surely to my hand and grasped my wrist. Ruthie and I both watched in fascination as Clarice brought my fingers up in front of her face. She smiled as she sniffed them then surprised everyone, including probably herself, when she opened her mouth and licked them. When she released my wrist she looked at Ruthie and asked, "Will there be some for me too?" Ruthie cackled and said, "He is a young stud so I think there will be plenty for you. So you are finally ready for this then?" With a red face and a shy smile Clarice nodded her head. I was about to start with my tongue on her hairy cunt. Ruthie stopped me. "Well stud, it looks like you are the one that will finally take my Clarice. She is 43 years old and has never even kissed a man. You are going to be a man someday, so it seems you will do for her. Is that right Clarice?" Her daughter nodded her head, her face crimson. The old woman got up from her bed. I watched the naked woman place her hands on her daughter's hands and lift her from the chair. Clarice was trembling and looked like she was going to cry while there was a demure smile on her lips. The naked woman hugged the clothed woman and she whispered in Clarice's ear. I didn't hear what was said. Clarice nodded and said, "Yes. This time. YES!" I was lying back on the bed watching the two women. I had developed a taste for virgins. I like their timidity and the awakening when the moment of losing the maidenhead occurs. I knew that not all had an intact hymen, but liked being the first since it hadn't been that long since I had my first. Ruthie beckoned to me. I rose from the bed and moved directly in front of Clarice. Ruthie stood behind her gently rubbing her back. I placed my hands on Clarice's face, moving them lightly over the reddened flesh. I held her face gently but firmly as I moved my face to hers. Remembering what she had done with her fingers moments before I started with Ruthie, I licked her lips lightly with just the tip of my tongue. She gasped then opened her mouth. Her tongue tip stayed just below mine as I moved on her lips. When I grasped her nipples lightly through the thin fabric of the sun dress her eyes opened wide and I was now licking a smile. I put my arms around her back and pulled her mouth to mine. We kissed tenderly then almost passionately while Ruthie continued to rub her back. Ruthie unbuttoned Clarice's sundress. She slipped the wide yellow straps down her shoulders. The front of her dress slid down from her breasts. She was wearing a blue bra that was made of material so soft and thin her nipples were very obvious. Ruthie unclasped her bra. Her breasts didn't sag much at all. Something to be said, I guess for never having suckled a baby. I was just guessing though. Behind her Ruthie's arms wrapped around Clarice and her hands cupped her breasts. I tugged downward on the sundress and it slipped to the floor. Dressed now only in a pair of blue panties with a major wet spot in front, her flesh covered in goosebumps, Clarice spoke. "Peter, I am a virgin, and I have been afraid of men. For some reason you make me feel comfortable." I smiled at her and kissed her lips again. Clarice pressed her breasts against my bare chest...then pulled back so the tips of her nipples touched my chest lightly. I moved my hands to her hips, grasped the elastic of her panties, then moved my face from her lips, down to move my cheeks, not yet dealing with shaving thus no stubble, lightly over her nipples, one then the other, finally pulling the panties to her ankles. Clarice's cunt was covered with hair as black as that on Ruthie's cunt. It wasn't as thick but every bit as pungent with the scent of a woman. I looked up to the face of the virgin. She was looking down at me. From below I moved my nose up the slippery opening swollen under the hair. When it reached her clit I moved the nub of my nose over the little nub she had there. Her cunt had the most delicious aroma. I inhaled it deeply, filling my lungs with essence of cunt. I rocked my nose back and forth on her slippery clit and soon brought my tongue out to lap at her juicy opening. Clarice put her hands on my head and moved her groin so her cunt lips mushed against my lips and up to my nose. She ground on my face until her hands gripped me so tightly I thought she would hurt me. Her cunt was moving quickly now against my mouth and then nose. She opened her legs wider seemingly trying to get my whole face into her cunt. I wasn't surprised when she started squirting and was just able to breath enough to keep from drowning under the high-speed flow. I lapped the stream into my mouth, swallowing as much as I could. I had it in my ears, all over my face and neck. It was AWESOME! When the squirting stopped she collapsed back into her mother's arms and started crying. She was smiling while the tears flowed. Later Ruthie told me Clarice had never had an orgasm like that and had certainly never squirted before. Ruthie and I helped Clarice to the bed. We took turns kissing her face, her lips. Clarice had her eyes closed. I kissed her eyelids then licked them gently. Clarice reached up, grabbed my head and pulled my mouth to hers. We kissed passionately for a very long time. Clarice's hand moved blindly down my body and eventually found my erection. She squeezed it lightly then traced her fingers over the entire engorged monster, learning the contours and feeling the precum that flowed from the slit at the tip. She brought her finger up, inspecting the clear slippery drop closely. She pressed the tip of her finger to her tongue to see if there was a taste. Ruthie whispered to Clarice loud enough for me to hear. "This is your first time honey. How do you want it? It might be less painful for you if you let Peter lie on the bed and you do all the moving. Or you could do it like it was for my first time. You remember my story about my uncle? Clarice nodded her head and thought about it. "Mother, I want my first time like this, on my back. I want my man to take me...to plunge into me with no regard to my pain." Ruthie smiled and said, "Charley was just like that...from his perspective he didn't care if it hurt me. He wanted it to hurt me. All in all though honey, it wasn't that painful. Just a kind of a pinch and then there was some residual pain, but I soon got over it." She kissed her daughter on the lips then moved to the chair. "She is yours Peter. Take her hard. She wants it hard and for you to do whatever it takes to get your own pleasure. Your mouth has already given her what she needs." I looked at the naked virgin on the bed and said,"Spread your legs Clarice." When she had done so I said,"Spread them more." She had her legs opened so wide she seemed uncomfortable. "Put your fingers on your virgin cunt lips and hold them wide apart for my hard prick. I want you to watch while I tear through your cherry." She had this frightened smile on her face, tears welling in her eyes. The virgin spread her lips and mouthed the word "now." My upper chest on my elbows, Ruthie assisted by guiding my cock to her daughter's cunt. Clarice gasped again when the spongy head of my cock pressed against the tight slit. Just from the wetness on the tip, I knew she was soaking, especially after squirting all over my face. I gave her a wicked grin and plunged hard and fast down into her cunt. I couldn't tell when the hymen tore, but was pleased with seeing cunt juice and bl**d on the shaft of my cock. Clarice was groaning as I fucked her. I had already fucked a woman earlier this day so my stamina and my age helped me go for a long time. Clarice was screaming and crying and then started to hiccup as I pounded her cunt. It wasn't until I started spurting my potent semen into her that I thought about the women I had already impregnated. I wondered if older virgins took contraceptive pills. I actually hoped Clarice didn't. The idea of making this woman, who was old enough to be my mother's oldest s****r, pregnant was right there in my lizard brain as I shot my very large load into her. I collapsed on her body when I had finished. Clarice put her arms around me and kept me from leaving her body. Fifteen minutes passed and she asked, "Can we...do it again?" I smiled at her and said, "Tell me exactly what you want me to do Clarice. I need a bit of encouragement." She looked confused and said, "I want you to...you know." Grinning again I said, "I need more than that. Where is my cock right now?" She thought about it for a few seconds and said, "It's inside of me." Right back I asked, "What is inside of you? I might need some words, very naughty words to get me hard again. You do want me hard again...right?" Clarice lay there nodding her head slowly, loathe to say those words, but finally she said, "Peter, your cock is inside my...my...." Ruthie whispered something in her ear. Clarice grimaced then said, "Your cock is inside my cunt Peter. I want you to fuck me hard again. I want to feel your hard cock opening me up and filling me. I want your come inside of my cunt. My cunt cunt cunt. In my CUNT! FUCK ME!!" That made me hard. I laughed and said, "There you go baby. Your second fuck is coming right....right...NOW! She screamed when I pulled away then slammed into her. The juicy sounds of our joining were delicious to hear. I felt fingers slip between us and thought it was Ruthie, but was pleased when I saw it was Clarice's fingers feeling my turgid shaft opening her cunt. Clarice started coming and coming HARD. She shrieked, she moaned, she yelled out "Fuck My CUNT!" I did so with vigor and after a good fifteen minutes of slippery sliding I yelled out, "Here it comes Clarice. My little baby makers are shooting again into your fertile cunt." She gasped then and I felt her cunt muscles squeezing my shaft, milking out all the semen. When we were done Clarice, Ruthie and I had a shower together. Ruthie gave me $200 and her phone number on a slip of paper after I was dressed and said, "Give me a call and we will set up another appointment Peter." I kissed both the naked women just before leaving the house and walking up to the bus stop. In fifteen minutes the bus pulled up. The same woman who had picked me up earlier was driving. She smiled almost knowingly at me as I stepped in a put my money in the machine. There were a few people way at the back of the bus. She held up the slip of paper that Ruthie had crumpled up before we got off the bus together. "I think this is yours. It says here "For a Good Time with a Young Stud Call...." Do I have to call this number to get some time with you or can we arrange something on our own." I was kind of surprised, but not that much because this woman was often my driver for my appointments. She probably wondered why I was going to so many different destinations. I asked, "Do you have a card...uh...," I looked up at the name on her badge and said, "Lana?" The woman, probably late thirties or early forties said, "My number is...." She told me her phone number and I said I would remember it. Lana grinned and said, "I am off on Thursdays. Are you available this Thursday?" I smiled my nicest smile then, repeated her phone number to her again. She nodded and winked. "What time do you get off tonight?" She told me. "I'll call you then and we can set it up," As I walked home from the busstop I thought about how nicely this summer was going.