I Was My Sister-In-Law's First (Well, Sort Of)

I first met my wife's half-sister Jennifer after we had been married for about 4 years. By then, my wife and I were into somewhat regular ********** with my wife's cousin. But her sister was only 16 at the time, so I wasn't expecting anything to happen along those lines with her, although in our state, it would have been perfectly legal. But that didn't stop her from saying, "Don't you even think about ******* her." OK, I was fine with that. A couple of years passed and my wife was killed by a drunk driver. A few years later, her sister came to visit me and the kids. I had set up my room for her to sleep in and I was going to sleep on the couch. But she said, "No, that's not right, I don't want to take your bed. You have a king size bed. Can't we just share it?" "Well," I told her, "Yes, we can. But I'll have to tell you now, I always sleep in the nude." She said she already knew because my wife had told her during her first stay with us in case she walked into our bedroom while we were still sleeping. Jennifer then added, "And that's no problem because I sleep naked, too."

That first night was kind of awkward. It was the first time we had seen each other naked, but I was a good boy and stayed on my side of the bed. During the night, I found myself with her cuddled up against me from behind, with her arm draped over me. When morning came, I was the first to wake up, but just laid there enjoying the feeling of a woman's naked body against me once again. When I detected Jennifer starting to arouse, I grabbed her hand and held against my chest so she could feel my heartbeat, which was clipping along as a pretty good pace. As she woke up, she pulled her hand away from my chest and to my surprise, she reached down and felt my rock hard ****. "Hmm, someone woke up horny this morning," Jennifer said. I rolled over onto my back so she could see me naked in the daylight and play with me for a while. While she was slowly stroking me, I reached up and played with her hair, then pulled her head towards mine and we kissed for several minutes, all while she continued to pump my ****. We then heard the kids in the living room, so we stopped, got up and dressed and went about our day. One of our stops was at a drug store. As we were looking for some things, I noticed the contraceptives section. I called Jennifer over and pointed to the different methods and asked, "Do we need to pick anything up from this aisle?" She looked up at me in a way which made me think she was going to say no, but instead she said, "Yeah, if you think we'll need it." Now, I couldn't very well ask her what THAT meant in the store, so I got some spermicidal gel because I knew one thing was going to happen if we ******. I was going to *** inside her. I just didn't know if it would be with or without the gel inside her.

That night was New Year's Eve, and after the kids were put to bed, at about 11:30 Jennifer said she had a surprise for me. She told me that at 11:55, she wanted me to be lying on the couch with the New Year's countdown on TV, naked and blindfolded, and covered up with a blanket. OK, I knew where this was heading but did not know how it would play out. As I could hear the countdown winding down to midnight, I heard Jennifer enter the living room. She was talking to me in a very coy manner, asking if I was ready for my surprise. "Do you know what it is?" I said, "I think so, but I'm not really sure." I could feel my heart about to beat out of my chest. Then the countdown got to 30 seconds and I felt the blanket lifted off of me, then Jennifer's hands stroking my ****, which was already hard. When the countdown got to 10, I felt her climb up on the couch with me and she counted down out loud, "10, 9, 8, 7, 6, 5, 4.." until she reached zero, at which point I felt my **** slide into her dripping wet *****. She reached down and took my blindfold off revealing a teddy she had brought with her and she began to ride me until I came deep inside her. I asked her if she had used the spermicide gel and she said that she didn't even look for it, but it was OK because she was still safe for a few more days. We wound up ******* on the couch until about 2AM. During our session, she admitted she had always wanted to **** me since the first time she met me, and she told me that she loved me. I told her that we better be quiet or we might wake the kids and "they'd see just how much I loved her, too." So we moved our fun to the bedroom, where I ate her out, performed anilingus on her, fingered her until she came (she, like her sister, was a squirter), and ****** her some more, each time dumping a now decreasing load into her. We finished about 5AM and fell asleep. We woke the next morning and showered together. Before we could get dressed, we wound up back in bed ******* again, then back to the shower, then we heard the kids awake again. So we finally got dressed and went about our day.

The kids were put to bed early that night and we took over the living room, with all the lights on for our fun. Jennifer laid down on the couch and pulled me over to her and started sucking my ****. About 5 minutes later, my wife's other sister called, knowing that Jennifer was there visiting us. I answered while Jennifer was still sucking me and made small talk with Crystal. She then asked to talk to Jennifer. Crystal and I, while we never actually ******, had a history. I think in the way I was making small talk, she had an idea of what was going on. I told her Jennifer couldn't come to the phone right now because "she had her mouth full," and she said, "Oh ****, is she sucking your ****?" I just grinned and gave the phone to Jennifer. All I could hear was Jennifer's side of the conversation.

"Yes, I was sucking it. What the **** do you want?"
"Yes, we've already done that."
"I LOVED it!"
"I don't know, you know I only did it once with that one guy."
"I know you've seen his ****, how do you think it felt?"
"Oh, **** you, *****, you're just jealous because I'm here ******* him and you aren't." (she was laughing when she said that)
"Dawn (my wife) was right, he does know how to make a woman feel good!"
"Just call me back tomorrow, we're busy here. And if we don't answer, **** off." (again, laughing)

I took the phone back and talked to Crystal for a few minutes, but Jennifer was insistent on continuing our activities. Crystal kept asking what we were doing at the time. "Well, she's still sucking me." "Now she's spreading her legs for me to **** her." "OK, I'm inside her now." "I'm going to put the phone down while we ****. You can listen." We ****** for a few minutes until both of us came, a little extra loudly for Crystal's benefit. After I came, I grabbed the phone and Crystal said, "Damn, boy! You two seem right together. Are you two going to wind up together? I know Dawn would have loved for Jennifer to help you raise the kids." I told Crystal I didn't know, but I had just left some ingredients inside Jennifer to make another. Jennifer looked up at me and smiled when I said that. Crystal was very supportive of the two of us being together and she told me "Good luck with making that baby and have fun!" before we hung up.

As the week wore on, Jennifer started getting close to her unsafe days, so our better judgment took over and we started using the gel, because the one thing we were not going to give up was me shooting my *** inside her, even if it meant a risk of us having a baby together. By the end of her stay, we had a chance to talk. I thought she was much more sexually experienced than she was until she told me I was her first in many ways. She had only has sex one time, with a guy she worked with, in a car, the the dark, with him wearing a condom. There was no foreplay and it was a rather quick "in and out" deal.

I was the first man to **** her without a condom, to *** inside her, to eat her out, to rim job her, to finger her, to make her ***, to make her squirt, to see her fully naked, and to suck on her breasts. My **** was the first one she had ever seen in the light, the first one she felt bare, the first one she actually jacked off, the first one she had ever seen shoot *** out, and the first one she had ever sucked. My ***, in addition to being the first inside her, was the first she had ever tasted, the first she had ever swallowed, and it was the first time she'd ever sucked on or played with a man's balls, and the first time she had ever sucked and bitten on a man's nipples. That made me feel good!

The next day, she drove back home about 500 miles away to her grandparent's house, who were opposed to her making the trip to visit us. They were fearful she wouldn't come back and that "something might happen between us." So I patiently waited for a month or two to see if she might call me to inform me she was pregnant, but that news never came. I think she just got all caught up in the moment because she felt sorry for me. I found out she met this other guy and and later married him. I believe thinking about ******* her dead sister's husband somehow made her feel regretful, but I'd do it all over again. I don't regret a thing!
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1 Response Oct 6, 2013

That was a fantastic story, I love reading stories where a man can satisfy a woman and the semi taboo of being your wife's sister is amazing.
You should feel proud that you gave her a great memory of being with a real man