I got fake junk responses, most wanting money until Debra answered my ad. Her response showed me that she was real and a dominant woman. Debra said she’d been married twice before and didn’t want a dick in her pussy again. She was a lesbian now but didn’t have a current partner. If I was true to my word, she said she would let me orally worship her pussy. Her email ended with, ‘I’m highly sexual and need my pussy eaten often. I’m a big woman, and I have a big pussy. I like to cum several times. Oh, and by the way, I’m mature, over 50, dominant, BBW, and very hairy; I don’t shave my pussy! And you must lick my anus too. Please don’t misunderstand me. I don’t like or want what you have between your legs, but if you perform well, to my satisfaction, you can jack off, or I may give you a quick hand milking occasionally. I’m waiting for your response.’
I was very excited to hear from Debra! She sounded nearly perfect. I wrote back to her promptly, and we exchanged facial pictures. Her face looked stern but pleasant. We planned a lunch date for the next day. Later that evening, I got an email again from Debra and was shocked to see she had sent me several nudes. She said she wanted to make sure I was attracted to her body. I could only guess she was about 220-230 pounds of voluptuous, beautiful curves. Her tits were nice and round but sagging, as you would expect for an older woman, and her nipples were excitedly protruding.
But her breasts did seem undersized, about like small water balloons, for her large, heavy body. A little disproportionate compared to her body, but I liked that. Her hips looked quite wide, and she had a small fat roll around her belly. Most exciting was the close-up pic of her pussy! So wonderfully hairy, even on the sides of her upper inner thighs! She looked amazing to me. I hoped I wouldn’t fall in love with this woman! I answered her email enthusiastically, telling her it would be my pleasure to submit to her pussy. She was happy to hear that.
The following day we met for lunch and sat in a booth. We got the small talk out of the way before we started talking about what our relationship would entail. We again went over her requirements if I wanted to serve her. She was kind but firm about what she wanted. No sexual penis penetration of any kind with her pussy or ass. No kissing. No blowjobs. Maintain mouth contact with her pussy as long as she requires. A minimum of three orgasms per session. Anal licking and tongue probing would be required. Do what I’m told. No questions asked.
She told me, “My tits are off limits, even if they are exposed. I sometimes play with my nipples during oral, but they are not for you. I will train you in pussy service to me. If you’re uncomfortable with that, we can cancel any further plans. You can back out right now. But I know what I like and what I will expect, especially since you’re a man and not my preference for a sexual partner. Be willing to learn and accept how I want things done. Always start by smelling me. Absorb my scent. When I tell you, you can plant several kisses on my pubic hair and then start licking my thick inner thighs. Lick my pubic hair over my mons’ pubis area and surrounding my pussy, and then give my pussy several soft kisses. That shows me your respect for my body and my pussy.
“Then you can begin in earnest. Finger me first. Start slowly until I’m wet. One finger at a time. But I can take up to four fingers after my pussy is wet and loose. You can use a vibrator on me, all around my clit, to get me wetter. After a climax, leave my pussy alone for a few minutes. You can suck on my toes while I recover. You don’t have to wait or ask for permission whenever I spread my legs. Just get your face back in my pussy until I cum again. I like to be licked from top to bottom of my pussy. If I hold open my pussy lips for you, I want you to go as deep as you can inside my pussy with your tongue. Focus on my clit when I tell you I want to cum. Sometimes I will face-sit you, knees on both sides of your head. Stick out your tongue and hold it firmly while I rock myself on your open mouth. I know anal can be humiliating for you, but it’s something I want. You’ll get used to it. For anal oral, I like to lay on my side and hold an ass cheek open for you. I don’t shave around my anus, so there will also be hair for you. Lick inside my crack and work your tongue up into my asshole. I like that feeling and may lay there for 20-30 minutes like that.”
I was listening intently as she talked openly to me. I hoped people around us couldn’t hear our conversation. She grabbed my crotch under the table, squeezed me, and said, “Do you understand me?”
I gulped, not expecting her to grab me there. “Um, yes, I understand.”
She let go of her grip. I’m sure she felt my hard-on.
“Good,” she said. “Let’s continue. I also like to be propped up on pillows for front and anal worship. Put pillows under my ass to lift my pussy up higher for your mouth. For anal, put pillows under my belly to lift my buttocks higher for you. Get on your knees behind me and open me up with your hands. That way, you can lick the inside of my crack and get into my asshole. Sometimes opening me up like that will make me pass gas. I won’t apologize for that. It means you were making me feel good, and I could relax. Consider it a compliment. I like a tongue licking and kisses on my butt cheeks too. Are we all good here?”
I was trembling a bit. “Yes, we’re all good,” I answered.
“Great! I’m going to the lady’s room now and take off my panties and put them in a plastic baggie I brought for you. I had an orgasm in them this morning before I left home. You will take them home and smell them. Please become familiar with my scent. Crave it. Open the bag and smell my panties often. Addict yourself to my scent. Intoxicate yourself with it. Masturbate while you smell my pussy in that bag! You will always smell my pussy before giving me oral.”
A few minutes later, she returned to the table and handed me the baggie in public! They were bright red panties in a clear plastic bag! I tucked them in my pants pocket. We set up a hotel room “date” for the following Friday night and made the reservation from right there at the table.
Our first time together in the room was rather short. We got to the room, and Debra wasted no time. She quickly kicked off her shoes and removed her pants. I could see pubic hair peeking out from the top and sides of her panties. I loved that look! She pulled her panties down and off and tossed them aside. I got my first in-person look at her beautiful hairy pussy. Her top stayed on, but she had a little belly roll that peeked down and under her top. Some wouldn’t find it attractive, but she looked sexy to me! “Let’s see if you remember your instructions,” she told me. She was still standing, now naked from the waist down. She put one foot on a chair and spread her chubby legs slightly. I remembered and knew what to do. I crawled over to her…to her pussy…and smelled her. She ran her fingers through her panty-matted pubic hair. I stayed on my knees, taking in her scent. She reached down with both hands and spread her pussy open. I breathed in more of her scent. She said, “You like the way my hairy cunt smells? Are you ready to service me?”
“Yes. Yes, please,” was all I could say.
She laid down on one of the double beds with her large bottom near the edge of the bed. Her legs hung over the side, and her feet touched the floor. I noticed her pretty, pink-painted toenails. She spread her legs, and I crawled between them. Her pussy smelled so good to me. Her scent was in my head already. I was practicing with the bagged panties she gave me earlier in the week. I licked her pubic hair and worked my tongue along her thick, creamy thighs. She began moaning softly as I approached her pussy. I started kissing and sucking her large, dark pussy lip flaps, her labia.
I like large labia lips on a woman. I gently sucked and pulled them with my lips. After a few minutes, she reached her hands down and opened herself up for me. Such a contrast. Dark pussy lips and so pink inside. I didn’t need to be told what that meant or what she wanted. I lapped at her sweet-tasting pussy. She let me lick for quite a while, and then she pulled back the hood of her clitoris, and I knew she was ready to cum. I tongued her clit until she climaxed. She backed my head out and closed her fat thighs together. Remembering what she had told me, I let her recover and went down on the floor and suckled her pretty painted toes. She wiggled them in my mouth, indicating that she enjoyed it.
She didn’t say anything to me, but about twenty minutes later, her legs spread and opened again, and I knew she wanted more. I brought my face to her pussy again, and she reached down to hold my head in place as she rocked m head side to side between her thighs while I licked her to two more orgasms in rapid succession. She told me to get her a washcloth and clean her pussy. She got dressed and left, saying nothing. No kiss. Nothing. We were there for about two hours, and I never had my clothes off. I went to my car with a full-on boner that night, aching inside my pants. When I got home, I took out the panty bag and masturbated while I smelled her in the baggie.
Later that night, I got an email from her. ‘Are you ready for more of my pussy?’
I set up our second ‘date,’ and we got another room. We live in a casino town and often get comp (free) rooms. Hotel rooms work best for us as we both have others at home. When we arrived, she said she was going to be naked this time and was going to lay back on the bed. I pulled the bed covers down, and Debra undressed right before me. She stretched out and raised her arms over her head while resting on the bed. She said, “I don’t shave my armpits either. Another hairy place you can lick for me!”
I thought, ‘Oh my gosh, this is my dream girl!’ Hairy armpits, hairy pussy, inner thighs, shaved legs, her little belly pouch, big fat ass, thick thunder thighs and calves, painted toes…yummy…so exciting to me. And I wasn’t allowed to touch those saggy “old-mom” breasts. Just looking at her, my penis was hard! I wished she wasn’t a lesbian so I could pursue her as a girlfriend. But I knew that wouldn’t happen. I don’t know if lesbians have a “look” or not, but something about Debra’s body and features told me she was a lesbian, and I should accept that.
She said, “We can try this with you being naked but put a condom on. I don’t want you leaking on me. And get a towel and put it between us.”
I wasn’t going to pass up this opportunity to be naked with Debra, but It did feel embarrassing to put on a condom and then be unable to lay next to her bare skin with a towel between us. I had to move the towel around while I serviced her so my body didn’t contact her directly. This time we were probably in bed for three to four hours.
After three orgasms, she wanted me to do anal for her. I had never done that before. She got on her knees, and I put the pillows from the other bed under her belly. She was propped up with her ass in the air. I started licking the backs of her thighs and working towards her twin globes. I started kissing her ass cheeks. My tongue licked into her crack.
“Open me up, Pussyboy,” she called out to me. “Do you like that hair back there? Lick me. Use your tongue in my asshole. I like how it feels. And I like humiliating you. You agreed to my demands. This is one of them. Lick me now, or I won’t be back! Get your tongue in me!”
I open Debra’s cheeks. She reached back and pried herself wider. I licked inside her crack and crept my tongue along until I reached her anus. I darted my tongue in and out of her asshole for several minutes.
She said, “Stick your tongue in and leave it in!”
I was leaking into my condom. I pushed my tongue into Debra’s anus and held it there as long as possible. I held her ass open, and it freed her hands. I had a beautiful view of her hairy armpits. She reached under and massaged her pussy while I tongued her sphincter. Her ass pushed back into my face as she had yet another orgasm. She collapsed on the bed.
I saw her pretty beaded sandals when I stepped out of bed to go to the bathroom and commented on them. I slipped my feet into them. Debra said, “Hmmmm, that’s interesting that you can fit and wear my shoes.” I didn’t think anything of it at the time.
After she recovered, she asked me to get her clothes and started to get dressed. But she stopped. She saw how hard I was. She said, “Do you want to look at my pussy and masturbate?”
I was taken aback. I didn’t know what to say and stood there with my head down. She said, “I’ll only give you one more chance. Do you want to look at my pussy while you jack off?”
I was still looking down at the floor, holding the towel, but I nodded affirmatively.
“I can’t hear you. Tell me what you want,” Debra said.
“Debra, please, this is so humiliating.”
“If you don’t tell me what you want, I can’t help you. And you’ll be going home with blue balls.”
“I… I… I want to look at your pussy and jack off, err, masturbate.”
She told me to put the towel down, and she went to sit in a chair, still naked.
She said, “You’re pathetic. Begging me to look at my old hairy pussy while you jack off! Come kneel in front of me.”
I did as I was told. Debra spread her legs over the armchair sides of the chair.
“Look at me. Look right at my pussy and jack off now.”
I started to remove my condom. “No,” Debra said. “I didn’t tell you to remove that. Leave your condom on. Cum in your condom. Get down on your hands and knees like a dog. Look directly at my pussy and jack off! Show me how you would fuck. Push your hips back and forth. Fuck your hand.”
My balls slapped back and forth under me as I moved my hips in and out. Debra’s hands went to her pussy while watching me on the floor, and she opened her labia lips. Her pink wetness glistened inside her pretty pussy. I kept looking at her pussy and let out a guttural scream and came. I filled the reservoir tip at the end of the condom. Debra told me to take the condom off and give it to her.
She took the condom to her worn panties and poured the contents into the gusset. She folded them up and put them in another baggie from her purse. She handed them to me and said, “Suck these panties clean when you get home.”
She got dressed and left.
Our next encounter turned out very different. When we entered our room, Debra went to bed at the far end of the room with her bag. She said, “Take off all your clothes and lay on that other bed.”
I thought this might be escalating quickly. I stripped down and started to get a little boner, naked in front of Debra.
She laughed and said, “Don’t get any ideas.”
I lay back on the bed with my legs dangling over the edge. I could hear rustling on the bed next to me. Plastic sounds like plastic being smoothed on the bed. Then I heard Velcro.
Debra said, “Come over here now. Lay down on this padding.”
It looked like a bed-wetting baby pad with an open diaper on top of it! I said, “What’s this?”
“Just lay down and put your bottom on the diaper.”
I was hesitant, but I followed her instructions. She never really saw my bare penis before. I was mostly outside her direct view, behind a towel or in a condom.
She looked down at me, saying, “Just as I thought. Small. No wonder you eat pussy.”
I felt embarrassed. Debra snapped on blue latex medical-type gloves on her hands. She opened a bottle of baby oil and poured some directly over my penis and balls. I was getting harder as Debra rubbed the oil into my skin. It felt more clinical than sexual, but at least she touched me. Debra told me to hold my legs up in the air, and she smoothed some of the oil on my bottom and dragged her oily finger through my crack. She pulled her gloves off, brought the diaper’s bottom-up between my legs, and fastened a Velcro tab on each side.
“I don’t want that thing between your legs touching me, poking into me, or pressing against me while you eat me. I’m not cruel. The oily padding should feel nice against your little weeny, and it will feel better to me tucked behind that padding! If you can cum from eating me and rolling around in your diaper, it will save me from letting you masturbate again later. Just don’t cum too soon. I know how you men are and lose interest.”
It was embarrassing, but I must admit, I did like the feeling of the diaper around me. I didn’t have to subject myself to Debra seeing my little penis jutting out. The diaper felt good for me with Debra. She seemed very pleased to see me in it. And I know this was to degrade me too, but I didn’t mind if I would get to service Debra’s body.
She was naked again in bed this time. She played with her nipples while I buried my face between her legs. She loved pinching and tugging on them and making her nipples erect. She would laugh at me and say, “No titties for you! Just my ass and pussy!” But later that day, after two or three orgasms, she allowed me to do something new.
She said, “Come lick my armpits. I know you’ve been dying to lick my hair.”
She was right. Her hairy underarms excited me. I’ve never seen a woman like Debra. At least no one in person. She stretched her arms over her head, and I laid down next to her right side first, with my face near her armpit. She ran her fingers through the hairs and said, “Go ahead and lick them.” And just as I did, she said, “Lick my armpits, Sissy!” Her words shocked me. It was the first time she called me that. Her underarms had a slight feminine flowery scent, obviously from her deodorant. I nuzzled her hair as Debra looked down at my puppy dog face gazing back at her eyes. She smiled and snickered, making fun of me for licking her armpits.
We usually got together once or twice a week. When Debra was especially horny and didn’t have a room lined up, she would call me to take her for a drive and go to a secluded park. Debra would undress from the waist down, and I would eat her in the back seat of my car until she climaxed. It was quick, but we both got what we needed.
We repeated the diaper routine every time we met for the next few weeks. I was getting used to it and just accepted it. I would undress and wait on the bed while Debra prepared the necessary supplies on the other bed. But this time, there was no diaper or pad on the bed, but she made me lay down on it anyway. Debra bent down and put something around my ankles, but it didn’t feel like a diaper.
She told me to stand up, and I saw they were panties! She pulled them up higher around my thighs, handed me a thick sanitary pad, and said, “Put this inside your panty, Sissy. It’s for my protection.”
She used the Sissy word again. She had used it several times with me before, and I just tried to ignore it. I couldn’t say anything. I just looked down, put the pad in my panty, and pulled them up.
We did our usual lovemaking with my mouth on her pussy for two hours. And she rolled over so I could give her anal oral again. I found pleasuring her back there becoming more normal and enjoyed seeing her big bottom propped up in the air for me. She would get out her phone and scroll, play games, and text people while I stayed behind her, lubricating her anus with my tongue for an hour or more. We both rested on the bed and fell asleep briefly afterward.
Debra got up, went into her bag, and brought out a pair of black pumps, about three-inch high heels, and a pair of nylons. Nude, thigh highs.
“Put these on,” she told me. I must have had a dumbfounded look on my face. “Don’t give me that look. You’re a Sissy. No normal real man would do what you do for me. Wearing diapers and panties. Licking my ass. You don’t fuck. No tits for you. Jacking off in front of me. Small baby dick. Sucking on my panties and eating your cum. How does it feel to be a Pussyboy, Sissy to a fat, hairy lesbian cunt? Put them on!”
I could only put my head down and blush, listening to her piercing, humiliating, but true words. I sat on the edge of the bed and slowly began to roll the silky stockings up my legs. The elastic bands held the stockings tight around my thighs. She laid her black-heeled pumps down before me and pointed to them. I slipped my feet into them.
“Stand up,” she said. I did so but felt a little shaky standing in the heels. “You’ll get used to wearing and walking in them,” she stated firmly. “Put your arms out in front of you.”
Again, I complied. Debra brought a pink, lacey bra from her bag, slipped it over my outstretched arms, and went around behind me to clasp it in the back. She took her phone and snapped several pictures of me!
“This is my insurance and for my amusement,” Debra told me. She then took my phone and copied my contact list! “Don’t worry, I’m sure I won’t ever need to use this,” Debra reassured me.
She put her bra and top on but remained naked from the waist down. My cock was stiff in my panties. They tented, even against the pad, pushing my panties out.
“See how excited you are?” Debra queried. “Only a Sissy would get so hard dressing up so girly.”
I hung my head and tried to cover myself with my hands. Debra went to her bag again, taking out a jar of Vaseline.
She said, “Pull your panties down and remove your pad.”
She handed me the jar. I took the jar from her, took the pad out, and my panties fell around my ankles. I felt foolish and ashamed. Debra took a few more pics of me and sat in a chair facing me. She spread her legs wide, but her top covered her pussy, but I knew she was naked underneath.
I had hoped Debra might touch me, but she casually said, “Use the Vaseline and start masturbating. Sissies use two fingers. Your thumb and index finger. Start wearing panties and pantyhose under your clothes at home and work. I want you to do two-finger masturbating daily in front of a mirror with your panties pulled down. Just before you spurt, I want you to let go of your penis, pull your panties up and cum in them. Use my panties and smell them while you jack off. You’re my Sissy now.”
Debra went to her bag again. She took out a dildo. It must have been eight inches of thick fleshy rubber with big balls. She sat down and slid the dildo under her top, hanging down, and I watched it disappear between her legs. I was getting hot and flustered. Debra knew it.
She asked, “Do you wish this was you?” as the dildo slid in and out of her pussy.
She was fucking herself, holding the rubber phallus by the balls, nearly taking it all, while she watched me masturbate wearing sissy clothes.
“Pull up your panties and cum in them,” she shouted.
She did too.
This was the start of something I never expected.
*This story has been edited to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story has been previously published on other free sites and is now public domain, which is why we can publish it here.