“My sinuses are killing me! Damned allergies! I’m taking some antihistamines and going to bed. Maybe Benny will help you clean up the kitchen.” Those were my words to my roommate Judy as I got up from the dinner table and headed to the bedroom.
We just been living together for a month after dating for almost a year. Our feelings were getting pretty serious and before we went any further she wanted to see if she could cohabitate with a male. She’d grown up with a single mother and younger sister while I’d been in a big family. When we met she was sharing an apartment with another girl. When her lease was up for renewal we decided to give living together a try.
So far it hadn’t been any more difficult than living with siblings but with the benefit of frequent and convenient sex. Judy was always ready and sometimes didn’t even need foreplay to get well lubricated for my entry, hence the nickname in the title which she seemed to get a kick out of.
My boyhood friend Benny came to visit on the rebound from breaking up with a longtime girlfriend. This was his second night with us and he and Judy seem to get along just fine. When Judy came to bed she checked to see if I was awake and I stirred a little bit. She rubbed her naked body on me, a common sign that she wanted to share it but I just groaned and said, “I think I’m worthless tonight. Why don’t you go make Benny feel good? I think his ego could use that after the way he got dumped.”
Judy asked in an incredulous tone of voice, “That would be okay with you? Are you sure?”
“You seem to think he’s an attractive guy and I’m sure he wouldn’t refuse a cutie like you so go make you both feel better.”
She gave me a big kiss, “Okay, see you later!” and left the room still naked.
I crashed again so missed any of the audio entertainment that might have issued from the front room.
Sometime before dawn I woke up and she was snuggled up behind me. Headache was gone and I had a morning woodie so I rearranged to be on my back and started tweaking her nipples. That’s one way she likes me to wake her up. She reached down and felt my rigid meat and rolled on top of me, expert me expertly, embedding me on the first stroke. Damn she was slippery!
She was all kisses and hip wiggles as she made her best effort to draw my seed into her body. I gave her the tit-play she loves and the hip angle for best clit stimulation and we both got off nearly together. She dropped onto my chest and said the first words of the morning, “Thank you for last night. It was good for both of us, both times.”
Hearing that I pushed my wilting weenie up inside her and gave her a big kiss with my response, “Well I sure enjoyed this thank-you too. I knew you’d get juicy and it’s a treat that I will tell you about after breakfast. If you want to go back and give him a wake-up call I’ve got to use the bathroom and get some coffee started.”
She gave me a fervent kiss, pulled off me and immediately put her hand to her crotch to keep from dripping as she headed for the bathroom for a quick piss and drain. And then she trotted back to the front room while I did my morning necessities.
As I was putting the coffee on I could hear the noises from the bed couch around the corner. As soon as the pot was started I walked out to take a look at the action. Judy had her legs up in the air and my buddy was plying his thick sausage at a rapid rate. Judy’s soft tits were bouncing back and forth with each solid stroke. She saw me out of the corner of her eye, turned her head, smiled, and threw me a kiss which I returned. It was just a quickie so as I watched his buns tighten as he unloaded his prostate inside my sweetie. She shivered and moaned her orgasm immediately after.
By the time they returned from the shower, coffee was ready and I started on breakfast. She took over, still naked, while Benny and I sat at the table. She was within earshot as I asked Benny, “I’m sure you slept well last night. Judy is the best sleeping pill I’ve ever found.”
Benny said, “Hey old buddy, it’s a lot more than that! The two of you sure know how to make a guy come out of the pits. I need to find a woman as good as this one, that’s for damn sure!”
Judy joined us, bringing the breakfast plates and sat down as I poured her some fresh coffee. She smiled at both of us and said, “I’m a lucky one too, you know. I’ve fucked a lot before I met you but none of them have ever demonstrated such sincere friendship to another man. Most of them were very jealous and sometimes accused me of things I didn’t do, even though I might have thought about them.”
My turn, “I said I would explain, so here goes. Benny and I were in the same grade at school and we’ve lived next door to each other since the sixth grade. When we started to wonder about sex Benny found some magazines his father had hidden and we looked at the pictures and read the stories and jacked off together. When we started dating we often doubled. I found a girl who would put out before he did. She was a hottie, kind of like you [grin] and she suggested that the two of us take her out to a drive-in. She took turns getting in the backseat with each of us, quite pleased with herself that she now had two virgins on her scorecard.”
Benny interrupted, “Do you remember the time that I took a date to the drive-in and you were with that girl. We’d each gotten it on before the intermission and they went to the bathroom and when they came back they switched. We dated them for quite a while when we could. They were pretty popular among the guys in our class and you can guess why.”
I took over again, “From then on whenever we could date a girl who liked to fuck, we would share as often as possible. We were surprised how many girls thought it was great fun. So you can see that what happened last night was not new to us. I gather you enjoyed yourself?”
In answer, my sweetie came over to my side of the table bent over and gave my cock a deep suck, and then did the same to Benny. “I’ve never had two guys one after another like last night. Will you both come to bed together and show me any other tricks that you learned?”
I need to mention that Benny’s dick isn’t as long as mine but it is real thick and his prostate is amazingly productive as Judy had commented. He had to leave the next evening but you can bet that her busy snatch didn’t dry out the whole rest of the time he was there. She told me it was great fun switching back and forth between such different man meat.
We laid in bed after he left, both of us pretty fucked out. Judy was marveling at how much semen he could put out even after repeated ejaculations. Giving me an impish look, she said “When is he coming back? I miss him already!” A few moments later she added, “Not really. It’s going take a little bit to recover from this but he certainly is welcome anytime as far as I’m concerned, just so you know.”
Benny was back two weekends later, not having had any luck in the dating scene, or so he claimed. The fucking was a bit less furious and we got out as a trio to go do some other kinds of entertainment as well.
After he left Lucy said that we needed to have a talk. “Uh, oh,” I thought.
She poured us each a glass of wine and sat on the couch so it sounded like a serious subject. I didn’t think I’d done anything wrong so was mostly curious. Was it about Benny? The weekend seemed to have gone well as far as I could notice.
Judy seemed to be struggling a little bit so I patiently waited. “This last weekend confirmed something that I’ve been thinking about. No, it’s nothing bad so take that worried look off your face. It’s just that you’re such a special guy that I don’t want to lose you. Will you marry me?” That last sentence was kind of blurted out and she looked a little embarrassed.
Wow! I didn’t expect that. Proposing was something I was supposed to do but I guess it’s really an equal rights thing. “If I say yes then that means we’re engaged, right? And we won’t get married for a while, right? Is there anything else about this I ought to know?”
She gave a big grin and said, “Yes to all questions. Regarding the last one, I would expect you to continue the loving and sharing like you’ve shown with Benny. I also want you to know that I would extend that hospitality to anyone you recommend and I trust you to make sure they were nothing but the very best.”
I reached for her hands and stared into her eyes as I said, “I accept your proposal and your conditions. Let’s set a tentative wedding date six months from now and if we make it as a couple that long then we know it’s good-to-go.”
Benny got the news when he was balls deep in my fiancé shortly after arriving, and since it had been two weeks he soon flooded her engorged pussy with a hell of a lot of juice. She was on her back so it didn’t drain out before I buried my rod in her swamp. It was a good thing she could use her pussy muscles to give me some traction and I watched her clean off his half-firm hose in her mouth as I pounded in my comparatively meager shot.
He treated us to a dinner out for congratulations and we caught up with his life. He hadn’t found a girlfriend yet but had met an older married woman who needed him between her legs couple times a week. No special affection, just satisfying basic needs.
Once again we had a fun and juicy time with several bonks each day and night he was there. He had to leave early Sunday morning and wasn’t sure exactly when he could come back again.
It was almost a month before he texted me about visiting again. He asked if he might bring his lady friend along. It seemed important to him so how could I say no?
Evelyn was in her mid-forties, a bit overweight and dyed blond but pleasant enough. We cooked in the first night and she was pretty helpful in the kitchen which gave Judi time to check her out. Benny and I sat out on the porch sipping some Wild Turkey because I figured he had some explaining about his companion. Sure enough, he did.
“Hey buddy, I owe you a bunch of pussy and I brought a pretty good one along. She and I got to talking and I told her how we did things and she was all hot to try it. Her husband is in jail for some bad business stuff he did. She hadn’t had any strange dick between high school and now me. We worked together and so she developed enough trust to spread em. I don’t know of it’s hormones or something but she’s been getting a lot hotter and ready to try new stuff.”
I responded, “She seems nice enough and I’ve never had anybody her age. She must be good in the sack or you wouldn’t be banging her, or were you just desperate?”
He slugged my shoulder as he said, “Well she’s not as good as Judy but then who is? I enjoy her plenty and I figured you would too. What does Judy think about this? We don’t have to swap if she isn’t for it.”
“I’ll find out later after she’s had time to check out your mistress.”
Judy and I went for a little walk after dinner was eaten and cleaned up. I figured she’d agreeable since she looked forward so much to feeling Benny’s big meat stretching her snatch. I raised the subject, “So what do you think of Evelyn? Do you think she’s good enough for me? Benny thinks so or he wouldn’t have brought her.”
Judy squeeze my hand, “Well I guess it’s only fair, at least logically. I guess I would trust his judgment since you guys have been such a fuck team for so many years. Who gets our marital bed?”
I squeezed her hand back, “Lenny’s spent plenty of time in it already so why don’t you take him there and I’ll do our new visitor out on the hide-away bed.”
Evelyn was kind of shy in this new situation with people she didn’t know so we turned down the lights and separated when it was bedtime. Judy and Benny even closed the bedroom door. We were still standing as I began to disrobe my new sex partner. I explored each of her newly uncovered parts with my lips tongue and fingers and her little noises indicated I was on the right track. When she was completely naked my tongue tickled her clit a little bit. I stood up and said, “Your turn!”
She copied my technique until I was naked. She wasn’t a very good cocksucker but she tried. I laid next to her on the couch and resumed stimulating her erogenous zones. Finally she tugged on my cock without saying anything, but I got the message she was ready to feel it inside.
She had a lot of fur at her crotch but the entrance was swollen and wet and easy for my dickhead to find. It only took a couple of pushes for our pubes to meet and she said softly, “Oh, it’s nice and long.”
I give each breast a quick suck and said, “I know I stretch you differently than Benny does.”
She pushed her hips back up at me and said “Different than my husband too. I love it!” No more words as we tried different things with each other and she finally had an orgasm when I really worked on her tits as I was pumping. Her hands on my buns urged me deeper until I sprayed her cervix with my juice.
I put my head down beside hers and laid on her ample tits. She gave me some little squeezes with her pussy. After a while she said, “So how did you enjoy an old woman?”
I raised up to look her in the eyes and said, “First of all, you aren’t old, just grown up more than me. And I liked it about as much as you liked having a hard young dick in you. Give me a few minutes and I’d like to enjoy you on top. Your tits are the biggest I’ve ever had my hands on and I want to play with them a lot more.” She giggled and I knew hearing that pleased her.
A long, leisurely fuck later, she snuggled down beside me and we snoozed for a while. At some indeterminate hour I awoke when somebody flushed the toilet. My companion was snoring lightly beside me when Judy walked in quietly and whispered in my ear, “Did she do a good job draining my favorite dick?”
I gave her a quick kiss and whispered in her ear, “She sure did and I’d be she’ll do it again before we get out of this bed.” Reaching for her pussy I felt the familiar wetness that I knew was Benny’s ample ejaculation still dripping out. Judy leaned down and sucked on my dick, tasting our juices before giving me another kiss and going back to her current fuck companion.
In the morning Evelyn wanted it doggy and I took the opportunity to play with her hanging and swinging big tits. She listened intently to the fucking noises from the bedroom and pushed back at me in synchrony with the thumping Benny was making.
After we both came I rolled us on her side and stayed embedded as we spooned. She chortled, “This is so hot! I never thought I would be doing this and my sex life would just stay as boring as my marriage. Thank you so much for helping me explore new things. Even if we never get together again, I will never forget this.”
My hand was reaching over and cupping her sagging breast. I tweaked her nipple as I said, “You’re more than welcome. This is a new experience for me too and that’s what keeps life interesting. Your visit isn’t done yet, don’t forget. I want to watch my buddy fuck you. What do you think of that?” She orgasmed just from the thought, surprising both of us.
Then he took her around town showing her things from his past while Judy and I took care of things that we needed to do that day. Although she never admitted it, Judy was very pleased I was keeping Evelyn occupied so she could get all of Benny’s thick and juicy dick that she wanted.
When we got back to my apartment the others were nowhere to be seen so I put a move on my companion. I knew she wouldn’t resist. We were soon fucking our parts senseless. Breathing hard as the glow subsided, Evelyn had tears in her eyes. “I never knew sex could be this much fun. I feel both thrilled and guilty. You understand what I mean?”
“Yes I do,” I responded. “In this culture we sure are messed up about sex and I’m still trying to sort it out myself. I’m glad I make you feel good and I love what we do too. You probably noticed that I’m okay with Judy’s freedom.”
She hugged me and said, “Benny explained that to me but I couldn’t believe it was real. Now I think I understand better and I think you two are really great guys. I hope I meet your expectations for fun in bed.”
I kissed her hard as I responded, “Loving you is a really good experience for me. You’ve opened my horizons a lot and I have to thank you for that. I will never let age be a criteria for having an intimate relationship from now on. I hope it’s all been good for you too.”
“Oh my God, yes! Having the two of you bed me has been the one of the greatest experiences of my life and I will never forget either one of you. Even if I do go back to my husband, which I’m really struggling with, my perspective on love and sex is forever changed. Don’t you worry, that is my issue to deal with but just know that you have really helped me a lot.”
“So where you go from here?” I asked.
“I’m not sure,” she replied. “I feel like I may be need to fuck a dozen more guys to get a perspective on the issue. But I’m not sure I want to do that, either. Why is it so difficult?”
I smiled as I said, “Sex is such a complicated thing that I don’t know if we ever really understand it.”
Six months later I got the text from Evelyn. She told me to meet her at a hotel at a specific time and I agreed. She was naked when I entered the room and immediately started sucking my quickly produced erection. Pulling me to the bed she said, “I’ve lots to tell you. Like I said last time, I have fucked 11 more guys to learn about sex. I want you to know that you are the best and I need more of you right now if you can manage it. I have been careful so my pussy is safe. Please fill me so I can feel the best man I have ever spread my legs for.
We fucked hard and long and repeatedly. Finally, I had to take her out for dinner since we were starving but we returned to the hotel and fucked again. Evelyn was incredibly affectionate. “I wish I could marry you but I am not legally divorced from my husband yet. I don’t know how you feel and I’m not trying to pressure you but I would appreciate it if you would tell me.”
As I gently moved inside her, I said, “You are a wonderful woman and I appreciate you dearly. You must realize that I am devoted to Judy who I love very much. We have some freedom in our relationship but we are really bound to each other. I understand your need and hope you can find someone who is right for you.”