Me and Judy - and her Mom!

Judy was my girlfriend, and had been now for about three months. After about two weeks, on my eighteenth birthday actually, she let me touch her breasts and now, after three months, we'd become fairly intimate. Well, she'd blown me twice -- she swallowed my cum, too -- and I'd eaten her pussy twice, first time on her eighteenth birthday. Basically, we'd done everything together except fuck. Oh, and I'd never seen her completely naked. Not yet, anyway, but I lived in hope, although what I had seen was well worth looking at!

We were both about to graduate high school -- the following week was our last - and then going on to college, and I think that's what made Judy's mind up, because we'd be going our separate ways. Me to study computer science, with a minor in electronics and Judy to study English language and literature. Anyway, one Wednesday in June she dropped her bombshell. I didn't know it was then, but I soon found out.

Judy lived with her mother, Janet, in a modest three bedroom ranch-style house a couple of blocks away from where I lived with my widowed mom. Janet was divorced from Judy's father and had been for about a year. I know Judy took it hard at first, because even though we weren't dating at the time, the high school grapevine is pretty effective at getting the scuttlebutt spread.

Anyway, like I said, it was a Wednesday in June. Judy and I had been to the movies, mostly so that we could kiss and cuddle -- and grope each other a little - in the dark, and we emerged into the warm, rosy twilight of a fine summer evening.

"Want to go and get a soda or something?" I said, but Judy shook her head.

"Not tonight, Ben, if you don't mind. Are you doing anything special on Friday?"

"Nothing planned. You?"

She smiled. "Mom is going to see my Grandma, and doesn't expect to get back until about midnight. Will you come around to our house?" She grinned. "We can play!"

I grinned back at her. "Play what?"

She shrugged, fighting another grin. "Oh, I don't know. Strip poker, maybe?" She arched her eyebrows in invitation.

"Sounds good." Good? Sounds fucking great!

She giggled. "Or strip snap, maybe -- it's quicker!"

"Okay, baby, it's a date. Friday at -- what time?"

"Seven?"

"Seven is fine, so see you at seven. Will I need the car, or should I just walk along?"

"Leave the car at home, Ben, we won't need it."

"Okay, I will, but what do you want to do now?"

"I'm a little tired, so take me home and we'll stop by Miller's Pond for a half hour or so." She grinned. "I think I'd like you to play with my tits while you're kissing me."

I grinned back at her. "I think I might manage that, madam. Tally-ho!"

It was more like an hour than a half hour, but I had duly played with Judy's tits. Not only that, but we'd fingered each other to very nice orgasms. When we stopped outside Judy's house, the drapes twitched and I knew it was Janet checking. One thing about Judy's mom, as long as she knew we were there she didn't bother us. Judy and I spent a few hot minutes necking, then she tidied herself up ready to go indoors. One thing I pride myself on, and that is being a gentleman, and I always got out and opened the car door for Judy, but as I moved to get out to do that, Judy stopped me.

"It's okay, Ben, I'll get myself out this time. You get yourself away, it's getting late, and I'll see you on Friday, at seven." She opened the car door, and leaned across to give me a quick farewell kiss, before getting out. As she closed the car door, she paused. "Ben? Before you come over on Friday? Get some rubbers, sweetheart, okay?" The car door closed, and she was gone, waving goodbye as she let herself into the house.

I sat there for a moment, feeling as if I'd been stunned, then grinned. Already got them, Judy, already got them! I started the car and drove the short distance home, grinning like an idiot.

*

Friday took forever to arrive, but the world turned, the days passed and at five to seven on the Friday evening I duly rang the doorbell. I was freshly showered and shaved, and I'd masturbated, too. After all, if what I hoped was going to happen happened I didn't want to take the chance of going pop too quickly, did I?

Judy opened the door and I felt my jaw drop, stopping dead in my tracks. Judy was naked, nude, not a stitch of clothing, totally unclad. Gorgeous.

"Quick, inside," she hissed. "before someone sees me!"

I got my paralysed legs moving and teleported myself through the door. Well, it felt that fast! With the door safely closed behind me, Judy was in my arms, in a heated kiss without end. Eventually, we broke it and Judy leaned back in the circle of my arms, smiling at me.

"Surprise!"

I laughed. "A lovely one, too. Judy Allen, you are absolutely fucking gorgeous without clothes!" I grinned at her. "It's great that my eyes confirm what my hands told me."

She giggled and held one foot out. "Not completely naked, I have my slippers on." She reached out and took my hand. "Come on, lover, my bed is waiting for us."

In her bedroom, the drapes were drawn, even though it was still daylight outside, and a low-wattage bedside lamp glowed warmly. Judy's bed was a double, I noticed. She turned to me and hung her arms around my neck, kissing my nose.

"You got the rubbers?" she said softly.

In response, I put my hand in my pocket and took out a three-pack. "I certainly did."

"Good, because I want to be fucked. Get naked, Ben. I want you."

"I want you, too, sweetheart, but are you sure?"

"Positive, Ben."

"Okay, sweetheart, with you in a moment." I began to undress, wondering why I'd hesitated. Heck, we'd done everything else, so fucking was the logical next step, and if that's what Judy wanted, then that's what Judy was going to get!

Judy's eyes never wavered from the area of my groin, and as I slid off my last garment, my boxers, letting my aching-hard erection spring free, she let out a gusty sigh.

"Ben, it's beautiful! May I touch?"

I grinned. "Please, sweetheart, be my guest." I gave her a quizzical look. "You've touched it before."

"Yeah, but not when I could really see what I was touching!" she said, gripping my cock lightly, her thumb rubbing over the head.

"Ah, yes. Of course. And?"

"Like I said, beautiful." She took my hand and tugged me towards the bed, letting herself fall back and pulling me down beside her. I took her into my arms and we shared another long, hot kiss. Judy broke the kiss and wriggled herself into the middle of the bed, spreading her legs. She grinned at me.

"You know what we're here for, so get that rubber on and get that lovely hard cock into my pussy and let's fuck. You don't need to worry about my hymen, I've been using tampons ever since I started menstruating."

I grinned at her and reached to my discarded jeans, and retrieved the condoms. It was the work of moment to open one of the little foil packets and unroll the condom onto my erection. I moved between Judy's spread legs, my weight on my elbows and pressed my hardness down, easing forward, feeling a thrill of pure lustful pleasure as the tip of my cock moved into Judy's warm, wet tunnel. She gave a soft moan as she felt me enter her.

"That feels fucking great, Ben, better than I thought it would. Fuck me, baby, fuck me good."

"Do my best, hon, be sure of that."

It took a few wriggles and a little to-and-fro, but I soon had as much of my cock in Judy's pussy as I could. I grinned up at her and she laughed. I began to move, thrusting into her, drawing back until I almost left her, thrusting in again, building a rhythm. Judy gave a soft moan.

"Oh, Ben, I'm loving it."

And that was the point we were at when Janet, Judy's mom, came into the bedroom. Judy screamed in surprise, then groaned, and I withdrew hurriedly, scrambling for something to cover myself, noting Janet's eyes flicker with some emotion when she saw my erection, before I managed to cover myself.

"When you're dressed, Ben, I want a word with you downstairs. I'll be in the sitting room," said Janet. She sighed and left the room, quietly closing the door behind her. Judy burst into tears. I reached out a hand to her, but she batted it away and buried her face in her pillow.

Sadly, slowly, I dressed, wondering why life chose to kick a person in the balls sometimes, then made my way slowly downstairs and into the siting room where Janet was sitting on the couch. She gestured to an armchair.

"Please, Ben, take a seat," she said and I realised, with almost a shock, that there was no anger in her voice. I opened my mouth to speak but she held up her hand, 'no'.

"Ben, I must apologise for bursting in on the two of you like that. It is unforgivable, but I must ask. Was that the first time for the two of you? Making love, I mean, or should I say, having sex, because I know the two of you have been intimate before."

And how would you know that, I wondered, but answered her. "Yes it was our first time."

Janet sighed. "In that case I'm really sorry I interrupted you. There are enough new sensations to experience, being interrupted shouldn't be a part of it. Understand, Ben, I'm not mad at the two of you, I was just taken by surprise. The two of you are legally adult, it's up to you whether or not you make love." She paused. "Ben, may I ask you a question?"

"Of course."

"Trying to find somewhere private and secure to make love can be difficult. If I let you and Judy make love in her bed once or twice a week, will you promise me you won't hurt her?"

"Mrs Allen, I promise that as long as Judy and I are a couple, and after, if we break up, I will do everything in my power not to hurt her."

"Thank you, Ben. How was Judy when you left her?"

"She was crying."

"Ben, I think the two of you need to finish what you started, and Judy needs to know what I've just told you, so let's go and tell her." She stood, and led the way back upstairs to Judy's room, tapping on her door and opening it to reveal a tear-stained Judy. She held out her arms.

"Come here, darling, Ben and I have something to tell you."

Hesitantly, Judy approached her mother, who drew her into a hug, kissing her cheek.

"Firstly, baby, I apologise most sincerely for interrupting what Ben tells me is your first time making love together. I'm truly sorry, sweetheart. Ben and I have had a little talk, and I told him what I'm now telling you. Rather than having the two of you sneaking around trying to find somewhere private, I'm going to let the two of you make love here a couple of times a week."

"You are? Oh, thank you, Mom, thank you!" Judy's face was radiant now.

"I'm going to leave the two of you now, to finish what you started. Ben? I'd like a word with you before you leave, please. I'll be in the sitting room. Take your time, children, don't rush it. A first time should be fun!" With a broad smile for us, she left the room, closing the door quietly behind her. Judy, a still naked Judy, looked at me in something like shock.

"Did mom just tell us to get back in bed and finish our fuck?"

"Yes, hon, I think that's exactly what she did."

"Well, get naked, lover, I always, well almost always, do what my mom tells me to do!" She laughed. "And knowing that my mom knows what I'm doing just makes me hornier!"

I have to say, for a first fuck for two relatively inexperienced people -- I'd only ever fucked once before, and that was a hurried affair at a party, and Judy was virgin -- we climaxed together in a wave of satisfaction. Washed, dressed -- well I was dressed, Judy stayed naked -- we sat on the bed together, kissing and caressing.

"Ben?" said Judy.

"Yes, hon?"

"I think I'll ask Mom if one of our bed nights can be Friday. Maybe we can spend the night together occasionally, eh?"

"That would be great, hon. You ask her and let me know."

"I'll let you know on Monday, in school. I'll be staying with my Dad tomorrow night. I stay with him every other Saturday. Mom doesn't mind; they may be divorced, but after all, he is still my father."

"Very true. Okay hon, one last kiss and I'll get myself away." It was a good one, and Judy''s lovely tits got a good groping, too.

Downstairs, I tapped on the sitting room door and went in. Janet was reading, but she put the book aside as I went in and gestured me to a chair. She'd obviously changed as she was now wearing a robe, and was bare-legged.

"A successful ending to your first fucking of my daughter, I hope?"

"Very much so, Mrs Allen. I managed to get her to climax."

"Well done!" A pause. "Ben, I have something to ask of you, something personal. Does the idea of sex with a woman of my age attract you or repel you? Be honest, please."

I gazed at her. Are you asking me to bed you, Janet Allen? Aloud I said, "If the woman was someone as attractive as you, Mrs Allen, it would attract me. I think I could learn a lot about sex, about pleasing a woman, from an experienced older woman."

"Good answer. Ben, Judy stays over with her father every other Saturday. On those days, will you come here and have sex with me, please this older woman? Jack and I may be divorced and there's no way I want him back, but I miss good sex and I think you might be able to provide it. I'm not asking you to cheat on Judy. If you agree, in principle, I'll clear it with Judy and get her written agreement for you before you ever touch me."

"Is sex all you want?"

"No, but it's all I'm asking for."

I pondered for a long, tension-filled moment, then nodded. "If Judy agrees, then yes. I will come and have sex with you on those Saturdays Judy spends with her Dad."

Janet smiled, a big, happy smile. "Marvellous. Now, I think you should see what you will be getting on those Saturdays, so what do you think?" And she stood, throwing the robe open to reveal her naked loveliness. No doubt about it, Janet Allen naked was every bit as nice a sight as her daughter.

"I think you and your daughter are both fucking gorgeous," I said, "and I'm very much looking forward to fucking both of you." I grinned. "I'd better give you my cell number so you can let me know whether, and when, to come tomorrow."

"Good thinking, hon." she closed the robe. "Now, give me that cell number and then you'd better go. I have a daughter to persuade."

Passing the cell number was the work of moments, and then she escorted me to the door.

"Goodnight, Ben, and thank you, both for pleasing my daughter, and for agreeing to please me."

I laughed. "Think about it, Mrs Allen, it's a win-win for me. "

She laughed. "So it is, and from now on I'm Janet to you. Now, kiss me goodnight."

It was a long kiss, a deep kiss, a kiss with deep meaning, and I ambled along to home thinking to myself, if Janet Allen fucks as well as she kisses, you're going to have fun, Ben Tellman.

I'd finished breakfast next morning when my phone pinged with an incoming text message, then pinged again before I'd opened the first message. I checked the senders. Yes, one from Judy, and one from Janet. I opened Judy's first.

Hi, sweetheart. Mom tells me she asked you to fuck her, and asked my permission first. I say go for it, give my mom a good time. See you in school on Monday. Love, Judy.

So, Judy was okay with me fucking her mom. I opened Janet's message.

Hi, Ben. As you'll know if you've read Judy's message, she's okay with us having sex. Can you come round after lunch, say about two? We might be able to manage more than once, if we're lucky.

Well Janet, if I have anything to say about it, we will! I prepared a couple of text messages, first to Judy.

Hi, sweetheart. Thank you for giving me permission to have sex with your mom. I'll try not to enjoy it too much :)

And one for Janet.

Hi, Janet. See you around two.

It was only around 9.30, so I had a long wait. I was wondering what to do when Mom solved my dilemma.

"Ben, honey? Would you mow the front lawn please, and tidy up the borders?"

"Sure thing, Mom."

Well, that would fill the time in nicely. I set to and was finished just after eleven-thirty. I cleaned up and then had a shower, get myself clean for Janet, before we got down and dirty.

Mom and I always had a light Saturday lunch, and today it was burgers, quick and tasty. I'd told Mom that Janet had asked me to help with a couple of chores and she'd been unconcerned so at ten to two I set off on the short walk to my appointment with Janet. She must have been watching for me, because the door opened as I went up the driveway.

Janet was out of sight behind the door and closed it behind me as I went in. I turned to greet her and my jaw dropped, as Janet was naked. She grinned.

"I just thought I'd remind you of what you're about to fuck."

"That image is engraved on my soul. Any chance of a photo?"

She studied me for a moment, then nodded. "Yes, if I can have one of you?"

"Naked?"

"Of course." She grinned. "With an erection."

I laughed. "Better take it before we start, in case I can't get him up again after."

"Come on, then. My bedroom awaits us." She took my hand, leading me up the stairs and into her bedroom. The drapes were open as the window looked out onto open meadows, a few cows grazing, no-one in sight. The bed was king size. Janet turned to me.

"Okay, Ben, get naked and let's take a few photos." She grinned. "Have you shot any nudes of Judy?"

I shook my head. "No, at least, not yet." I'd been undressing as we spoke, and as i discarded my final garment, my boxer shorts, I turned to Janet. Her eyes went straight to my groin and she grinned.

"Only a little more work before he's ready for my pussy. Lay on the bed and let me at him."

I lay back on the bed and Janet knelt astride my legs, bending like a cat to take my almost completely hard cock into her mouth, a few strokes of her tongue and John Thomas was ready. Janet sat back on her heels and grinned at me.

"That's a very nice cock you have there, Ben, bigger than my ex's I think, definitely thicker. Stay there while I grab my phone."

The work of moments and then Janet took a couple of shots of me. She paused, glancing at the photos, then passed her phone to me, an iPhone 8, like my own. One shot was a full length shot of me, the others were close-ups of my cock.

"I think you look pretty damned good, Ben, I can remind myself of this moment while I play with my dildo. Now, you wanted to take my photo, so where's your phone, and how do you want me to pose?"

"My phone is in my jeans pocket," I said, scrambling to retrieve it, "and I'd like a simple standing pose, a kneeling shot, a reclining shot and, pretty please, one of your pussy, then another shot with my cock inside you." I held my breath, waiting for the explosion, but a slow smile spread over Janet's face and she nodded.

"Yes, those shots I want to see myself. Okay, honey, your model is ready!"

First shot was a simple standing shot of a relaxed Janet, one hand on a hip, the other resting on her thigh, then a kneeling shot, Janet resting comfortably on the bed, then she lay back and spread her legs and I saw a mature woman's pussy for the first time, flushed, slightly open, visibly moist. A couple of quick shots, and then I sat beside Janet as we reviewed the images. Janet laughed.

"If I wasn't already wet with anticipation, I would be after seeing those shots. Will you send them to me?"

"Of course, if you'll send the shots of me?"

"Deal! Now, I think a certain young man said he wanted a shot of his cock in my pussy, yes?"

"Please."

"Okay, pass me your phone. I want this first time for us to be plain missionary, so as soon as I've taken the picture I want you to fuck me, fast and hard this first time, plenty of time to experiment later. Okay?"

"Absolutely." I paused. "Um, do I need protection? I have some rubbers in my wallet."