Helping Out

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Mar 14, 2023 // By:analsex // No Comment

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When I came home from work, I was surprised to find Jennifer’s car in the driveway. I hadn’t expected to see it there, as the last I heard they hadn’t planned on coming up again for another several months.

I pulled my car into the driveway and gathered up my stuff. As I opened the front door, I heard my wife and her sister talking. They were sitting at the kitchen table, Jennifer beside her new husband, my wife sitting across from them. All three had rather guilty looks on their faces, I thought at the time. I should have realized something was up then.

I greeted them and made small talk for a couple of minutes before going into the bedroom to take a shower. Lissa came in while I was showering and told me that when I got out that Jennifer and Nathan were taking us out for dinner. She had some clothes laid out for me on the bed and after dressing, we all left.


The food was excellent, and we had a great time, but I could tell that there was a slight undercurrent of uneasiness at the table. Nathan’s laugh seemed a little forced sometimes and Lissa kept looking at Jennifer with a strange look. A couple of drinks after dinner and it all came out.

“Jesse, I’ve told you that Jenn and Nathan have been trying for children since they have been married, haven’t I?”

“Yes honey. You did. Why?”

“Well, they finally decided to get some medical help, and that was when they found out that Nathan is sterile.”

“What? Jeez, I’m sorry Nathan. It must be tough.”

I felt bad for the guy. I knew how badly he had wanted to have children, and I knew that he would be terrific with them. Watching him play with Lissa’s and my kids had proven that. He was a good man, and I genuinely liked the guy. His face was bright red and I could tell that he was having a hard time dealing with it.

“Thanks Jess. When I found out, well, it was quite the shock.”

“Shit, I’m so sorry.”

Jennifer took her husband’s hand in hers and turned to me. “Jesse, we were wondering if maybe you would be willing to help out.”

A shiver ran up my spine as she said the words. The guilty looks from earlier were all explained. I knew then exactly what it was that they wanted, but decided to play dumb. A long time fantasy could be mine if only I played my cards right. I felt bad taking advantage of them in their time of need, but I also knew that there was no other way that I would ever be able to do it.

“Me? I’m not a doctor Jenn. How can I help?”

“Well, this is very difficult to say, so I’m just going to blurt it out. We know you are very fertile Jesse. Would you be willing to donate some sperm for us?”

I tried to put on my best surprised look on my face and by the reactions around the table I could tell that it had worked.

“It’s ok honey, I’m cool with this,” Lissa said as she grabbed my hand.

“The doctors can do all the rest Jess. You won’t have any responsibility other than being a good uncle, we promise.”

I looked into Nathan’s eyes. He was very nervous about this, but wanted it so bad it showed. I told Lissa that I wanted to talk with her in private and we left the table. Jennifer and Nathan looked very worried.

“Lis, are you sure you are cool with this?”

“Jess. I love you. I also love my sister. I’m willing to do this. Could you please do this for me?”

I stalled for time and Lissa took it as me being my normal difficult self. Finally I spoke.

“I don’t know if I’m ok with this honey. I mean that I can handle that my child isn’t with us. That is easy. I know it will be well cared for. But I can’t handle the fact that it will be made by some doctor with a turkey-baster. It’s just so unnatural. I can’t.”

“Jess, that’s not how they do it.”

“I know Lissa. But you know what I mean.”

“So you won’t do it.”

“Not that way, no I won’t.”

Lissa looked at me for a minute, then she suggested something that I was trying to find the way to say myself.

“What if you did it the old-fashioned way?”

I didn’t have to try and fake the shock on my face this time. It was genuine. Never in a million years did I ever think that my jealous wife would suggest such a thing. It made me feel guilty, made me doubt my little plan.

“What do you mean? I should fuck her?”

“Jess, I know it seems strange. But they really want a child and we can help. I’m willing to help out my sister in any way I can. If that means that I have to let my husband impregnate her, well, as tough as it will be, I can handle it. Will you do it for me? Please?”

I pulled Lissa in for a tight hug and whispered in her ear that I thought she was such an amazing person. She pulled back and smiled at me.

“So will you do it?”

“Well hon, I don’t like the idea much, but for you I’ll do it.”

Her smile widened, and she took my hand and led me back to the table. As we sat down, I saw Jenn grab hold of Nathan’s hand once more and they looked up into our eyes with hope in theirs.

“We too hot to handle latino izle have talked about it, and decided that, yes, Jesse will help.”

Nathan and Jennifer started to thank us profusely. Lissa held up her hands and asked them for quiet.

“Hold your thanks. Jesse and I have some conditions. Neither of us is very comfortable with our future niece nor nephew being born a test tube baby. If you still want our help, the baby will have to be conceived naturally. Or you will have to find someone else to be a donor.”

Jennifer and Nathan looked at each other with a look of complete surprise. Nathan looked at me and Lissa with a strange look. I tried my best to look determine to do something I wasn’t at all happy with, while inside I was dancing for joy. Jennifer looked at Lissa then at me with the slightest hint of a smile on her face.

They excused themselves for a minute and went outside. While they were there, I tried half-heartedly to talk Lissa out of it, all the while knowing that every word was in fact making her more determined to go through with it.

Nathan and Jennifer came back in with wide smiles on their faces and thanked us for helping. They paid the check and we drove back to the house. The next day they left, saying that they would plan out Jennifer’s fertile days and make a date for us to try and impregnate her.

* **

I knocked on the door to the hotel room, and I’ll admit to myself that at that point I was a little nervous. When Jennifer opened the door though, all that nervousness left me. She was standing there wearing a thick cotton robe. Her long dark hair was still slightly damp. She had obviously just had a shower.

I had just finished work for the week and had my overnight bag in my hand. After exchanging our greetings I went into the bathroom and had a nice long shower. I shaved before coming out of the washroom and looked around the room.

We had decided that the best way to do this was for Jennifer and I to have a full weekend together without interruption. Nathan had rented us a suite at one of the better local hotels, complete with a Jacuzzi tub. The room was beautiful, in any other setting I would have found it very romantic. I could imagine sitting here drinking wine with my wife. But in this case I knew things were very different. I found out later that I wasn’t the only one who had expressed concerns about what was going to happen to my spouse, so Nathan had thought ahead.

He had come up with Jennifer and was staying at another hotel close by. As I looked around, I saw that he had hooked up a VCR to the TV and a large stack of movies was beside it. By the cover of the top one I guessed them to be all adult oriented. Brand-new packages of lube were stacked on the night-stand. There were even a few candles scattered around the room. Nathan had thought of nearly everything.

I looked over to see Jennifer sitting at the table, still dressed in her robe. She was smoking a cigarette, something that she had given up a long time ago, but obviously the stress of what was going to be happening over the next two days and nights was putting a slight strain on her.

I pulled out a chair at the table and sat down. Taking one of her cigarettes I lit it and took a long drag. I looked up into Jennifer’s eyes and saw the nervousness there. I reached over and took one of her hands and gave it a slight squeeze. She smiled at me and squeezed back.

“Jesse, I don’t think that anything that happens here this weekend should ever leave this room.”

I smiled. That was exactly what I had planned on bringing up. Jennifer looked very relieved and a lot less nervous when I agreed with her.

“But Jennifer, there are a few things I need to talk to you about before we get down to this difficult task,” I said with a shit eating grin.

That brought a laugh, exactly what I had been hoping for. Jennifer was a lot more relaxed and sensing this, so was I.

“First off Jenn, I have to admit the truth. I have told Lissa that I didn’t really want to do this, but I would for her. That is a lie. I want this. I have fantasized about you for years. I never ever thought that I would have the opportunity though. I don’t believe in cheating. But when you suggested using my sperm to inseminate you, I knew that this was the perfect opportunity. I’m sorry if you don’t feel the same way, but this isn’t going to be difficult for me at all. I will love every minute I’m here with you, and I even hope that you don’t get pregnant this time, so it can happen again.”

I was once again nervous as I told her this, I half expected her to start screaming and run from the room. When I looked up into her gorgeous brown eyes I saw a huge smile.

“Jesse, I so glad to hear that. I lied to Nathan as well. I told him that I wasn’t to keen to sleep with you, but I let him convince me otherwise, all the while I was looking forward to this too. I’m treason izle the one who talking him into renting us this room for the weekend.”

A smile split my face as she told me this. This would make the rest of my demands easier to make.

“Jennifer, you never cease to amaze me. I have some requests, however, that you may not like as much. I like to play when it comes to sex. I don’t want this to just be a wham bam thank you ma’am kinda deal. Everything I can do with Lissa I want to do with you, and more.”

“What do you mean Jesse?”

“I mean foreplay for starters. I like it a lot, and I want us to do that too.”

“That’s fine with me. Nathan is a rather boring lover that way. He just wants penetration, the best I get is he plays with my breasts a little.”

“Good. I’m glad you agree. Another thing is that I want to cum in places other than your pussy. I think every fourth one should be somewhere other than there. Think of it as my payment for doing this.”


“Everywhere Jenn. In your mouth, on your face and breasts and in your ass.” I could see the strange look creeping up on her face so I thought I would lay all my cards down on the table right away. If things were going to go sour, might as well have it happen up front. “I also have borrowed some things from a friend of mine for this weekend. I want pictures and videotapes of everything we do. If you have a problem with this, we can always stop here and tell our partners that we couldn’t go through with it.”

Jennifer looked very torn as I said my piece. For a minute I thought she was going to call it off. When she started to talk I realized that my fears had been unfounded.

“Do you have to fuck my ass?”

I would have smiled, but instead I put on my best poker face and told her that yes, I did or the deal was off. While she stayed silent for several more minutes, I knew that I was going to have a wild weekend.

“Alright. I agree.”

I got up from the table and opened my bag. From inside it I pulled out a tripod, a digital video camera and a digital camera, complete with several cards for each. Reaching back inside I pulled out a laptop computer and placed it on the table in front of us. Several blank CD’s followed. I placed the camcorder on the tripod in the center of the room and asked Jennifer to come over to me. She stood where I told her to, and as I hooked up the laptop to the camera, she stood there watching with a little nervousness.

Once everything was set up, I picked up the digital camera and sat on the bed.

“Take off your robe, slowly.”

Jenn smiled at me as she untied her robe. I could tell that she was quickly getting into this. Her gorgeous smile and perfect teeth were the first of the many pictures I knew I would be taking. She was quite the tease, lowering the robe just enough to bare her shoulders. The thin red straps told me that she wasn’t naked underneath her robe, which suited me just fine.

As her ample cleavage slowly started to be exposed, I felt my body starting to react to the show in front of me. In seconds the front of my cotton shorts were tented out. Jennifer was really enjoying her little tease, taking her time in removing her robe. First she showed off her legs one at a time, covering everything but the flesh of her leg all the way to her buttocks. Silky red stockings that matched the bra she obviously wore covered her gorgeous legs.

She was a big girl, but I thought she was just so sexy. When she finally lowered her robe to her waist I nearly came. Her silk bra only covered the lower quarter of her very large chest. It had the effect of making her large breasts push up and out from her body, seeming to defy gravity. She had smaller nipples but they were very hard and pointed straight out.

Jennifer lowered the robe to her waist then suddenly dropped it completely. The sight of her standing there was almost too much for me. Holding up the silk stockings was a matching garter belt. Over top of this she wore a pair of red silk crotch less panties. I could see how turned on she was. Hell, I could smell her arousal. It took all of my self-restraint not to throw her on the bed and slam my throbbing cock deep inside her. The front of my shorts had a slowly spreading wet spot that I knew Jennifer could see by the way her eyes were drawn there.

“Jenn, you’ve always told me how much you like to suck a guy, I think now its time for you to show me.”

Smiling at me, Jennifer held out her hand to help me up. I stood up and pulled her into me. My hard member was crushed between our bodies. She was so much shorter than me that I could feel her breasts on the tip of my cock. I lowered my face down to her and at first our kiss was hesitant. As she started kissing back it became more passionate, hungry even. I could tell by the kiss that I wasn’t the only one who had fantasized about us together. My hand found her breast and as I ran my fingertips lightly over the true detective izle hot skin Jennifer moaned around my lips. With lust filled eyes she broke our embrace and put both of her hands inside my shorts.

I kept looking into her eyes as she stroked my cock, both my hands now on her breasts, lightly teasing her nipples. With one quick motion Jenn slid my shorts down and I stood naked before her. Her eyes opened wide as she took in my arousal.

With a wide grin on her face she spoke, “Wow Jess, Nathan is about the same length, but you quite thicker. This will be tons of fun.”

I smiled in pride. I knew I was no porn star, with a dick that hung to my knees, but at the same time I also knew that I had a larger than average cock. Hearing her talk about me in that way, with the lust nearly dripping from her voice was quite the confidence boost.

Jennifer knelt before me with her hand never leaving my swollen cock. I was so aroused that my dick had sprung a leak. Her hand was covered in my pre-cum. Instead of starting on my cock, Jennifer pushed it up towards my belly and leaned in close. Her first light kisses on my shaved balls were like fire, sending shivers right up my spine. Her tongue felt divine as she slowly started to bathe my balls with light licks. I watched as she buried her face in my crotch, kissing and licking my balls, teasing my repeatedly.

Some of my pre-cum had dripped from the end of my member and had fallen onto her forehead. Right there, at that exact time I knew she was the most sexiest woman I had ever lusted after. I loved her sister with all my heart, but that love was chaste compared to the pure unadulterated lust I felt for the gorgeous woman before me.

When Jennifer’s tongue started up my shaft I thought I had died and gone to heaven. She licked around my head and shaft for a long while, cleaning up all of my excited mess. When she finally took me into her mouth I nearly filled her with my cum. Without pause my cock was instantly all the way back into her throat. She pulled back slowly and throated me once again. The whole time she never took her eyes from me. Less than a minute into this perfect blowjob I knew she had to stop.

When I backed away from her, Jennifer looked upset that I had stopped her, but one look at my face and she knew why I had stopped. When told, Jenn quickly lay back on the bed with her legs spread wide for me. Her panties were soaked, as were the tops of her stockings. I lay down between were spread legs and quickly slid inside her wet pussy. I nearly lost it on the first stroke. She was fucking tight!

Jenn wrapped her arms around my shoulders and her legs around mine. We kissed deeply as my cock drove for the first time into the depths of her womanhood. Jennifer me each of my powerful thrusts with one of her own. I felt my orgasm building and as my pace increased, Jennifer lowered her arms from my shoulders to grab my ass, pulling me into her in time to each of my own thrusts.

Jennifer started to talk dirty right then, just before I peaked. As soon as she told me to fill her cunthole with my juices, I lost it. With a loud grunt and a powerful thrust that opened Jennifer’s eyes wide, I emptied my seed deep inside her pussy. I ground myself on her cunt, trying to get in as deep as possible. As my orgasm started to fade, I once again started to kiss her. This time a lot more tenderly. The passion was still there, just not as much hunger as my immediate need had been sated. Jenn pushed me off of her and pushed me down onto my back

She took me into her mouth and sucked me, fondling my balls with her hand. She stopped suddenly and sat up, all the while she kept stroking me. Her lips were coated in a mixture of our juices and with a little laugh and a wide smile she licked her lips.

“We taste good together Jess.”

That made me laugh, and together we had a long chuckle. Once she had composed herself Jennifer bend back down and took me back into her mouth. I ran my fingers through her gorgeous long hair while I watched her mouth on me. She hadn’t lied to me about her love of sucking cock, but she sure had understated her skill. Within minutes I was nearly ready to blow.

Almost as if sensing this, Jenn straddled my waist and with a hand between her legs lined up my cock with her bald pussy. She slowly lowered herself onto my cock as I again marveled at how tight her cunt fit around my cock. Jennifer leaned back and put her hands on my shins as she slowly fucked my stiff muscle. I watched as it disappeared inside her. All that moved was her hips, slowly up and down on my cock. Her big breasts wobbled with her movements, and I knew exactly what I wanted for my first payment. I reached over and grabbed the camera, snapping a couple of pictures of her cunt doing its best to milk my dick.

Jenn’s breathing quickened as did her pace. She looked me in the eyes as she shuddered. I watched as her clear juices squirted from around my cock, soaking my balls. Just the sight of her cumming around me set me off, and I thrust as well as I could deep up into her body. I could tell Jennifer was spent as she leaned forward and lay on top of me. Our bodies remained joined at the waist while we lay together. I ran my hands up and down her back We kissed as we lay together until finally Jennifer got up off of me to go into the washroom.

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