1 comments/ 21273 views/ 13 favorites A Unique Relationship Ch. 00 By: Secretlit777 I would occasionally babysit for the couple across the street. Just into their forties they had two kids in elementary school. They lived in a very nice house with pool and all, and they drove very nice cars. They got divorced one summer. I had just turned 19 and was attending a community college only a few minutes from my house. I still would babysit for my neighbor, Lori, from time to time, because the money was easy and plentiful. Lori is in her early forties, but she doesn't look a day over 25. Pale skin and 34B breasts (I have snuck a look at her bra while babysitting a while back) compliment her toned ass and flat stomach. One August night she became mine. At age 19 I was 6'4" 190 pounds. Almost washboard abs and large toned muscles every where else. I walked over to Lori's house one night to watch her kids. Now at ages 12 and 10 I really didn't think that they needed a babysitter, but I didn't mind getting paid to play video games and watch sports with them. I knocked on the door and Lori answered, "Hey Jim! I'll be ready shortly." She looked absolutely stunning. In her black dress that hugged her toned body and showed off her nice legs. "The kids are in the media room." "Ok." I walked towards where the kids were. Lori looked damn hot. Her breasts looked larger than usual too. I said my hellos to the boys set down my laptop and went into the kitchen. A few minutes later Lori emerged now wearing black pantyhose along with her black dress and high heels. Her hair was usually some shade of a dark red, but since the divorce she had colored it a dark sandy blonde, and it reached down the middle of her shoulder blades. Her usually pale skin now had a nice tan to it. Being August I assumed it was a natural tan from her summer time in the pool. "Alright Jim, you are ok with staying the night?" "Of course. Tomorrow is Saturday so it's no big deal." "Thanks a lot. I will have your money for you in the morning. Wish me luck on my date." "You look great. He is a lucky guy." She flashed me a seductive smile and was out the door. I looked out the window and saw her new Mercedes roaring down the street. What a MILF. -------------------------- The rest of the night was fairly uneventful. Video games, pizza, and a movie before the kids went to bed. I was off the clock by 11:00. I made myself a place on the couch and fell asleep watching Sportscenter. I awoke when I heard a door open. I looked at my phone, it was 3:00 am. I got up and walked through the house in only my boxers. I went into the kitchen and was surprised to see Lori there. "Lori?" "Oh! Jim you startled me." "Why are you home already?" "My date didn't go as planned. One of my friends set me up with him. He is a slob. Hairy everywhere and overweight."She stopped and gave my body a once over. Being startled out of bed I was only wearing my boxers. She eyed my defined stomach and toned arms. "Well that is too bad. I'm sorry. Give me five minutes and I'll head home." "No, no. It's three o'clock in the morning. Stay." "Umm, ok. I would probably scare my parents anyway setting off the alarm at this hour." Lori turned towards a cabinet and said, "Would you like a drink? I have some wine, scotch, and some beer in the garage fridge." "I actually don't drink." "I usually don't either. It's all of my ex's left over stuff." She sighed with an obvious look of regret on her face. "I really miss having a man around. My boys aren't old enough to be men of the house yet. I hope they will grow up fine without a strong male presence." "Why won't they see their dad?" "He ran off with some blonde 25 year old. Took all of our savings. Millions. Once they tracked him down he had blown most of it on some house and cars in California. I got only 2 million of that put into my savings and a $200,000 settlement. Child support is $5,000 a month and he has to put $1,000 a month into each of their college funds. I guess I came out good in the end, but he's the one with the hot new wife while I'm here dating obese hairy men." She began to cry. Leaning against the kitchen counter she began to sob into her hands. I really didn't know what to do. I walked over and placed a hand on her shoulder. Gently enough as to not show affection, but strong enough to show that I was here for her. "He lost you too. You're kind and caring. Plus he won't get to see his own kids until who knows when." She stood straight up and reached her arms around me, pulling me into a hug. I wrapped my arms around her neck and our bodies pressed together. We stood like that for maybe 20 minutes. She would sniffle from time to time, but after a while she began to compose herself. I surprisingly didn't get hard with her hands on my bare skin and my cock pressed against her flat tummy. We removed ourselves from the embrace and we faced towards each other. She took one of my hands in each of hers and placed a kiss on my cheek. "Thanks for being here for me Jim. It's nice to talk to another adult. My kids aren't old enough to understand this, and no matter how stupid my ex-husband is I will not bad mouth him in front of his kids. He can make himself look like an ass on his own." She walked over and fetched a tissue. She ran it across her face cleaning up her makeup that had run down her face. Lori said, "Well I am a mess. Where were you sleeping?" "On the couch." "That's not very comfortable. Why don't you come sleep in my bed." "I couldn't." "Please Jim. I insist, we are both adults here. The bed is plenty big for two people." Both of us being adults is exactly what I was worried about. "Ok, since you insist." Can't say no when teenage hormones are in the mix. "Pour me a glass of wine and meet me in my room. I will go change." She exited the room. Rubbing her freshly manicured nails across my hard stomach, sending a jolt into my flaccid penis. I did as I was told and entered her room with a glass of wine. I sat down on a chair in the corner of her room waiting for Lori to exit the bathroom. I had also cleaned up my prior sleeping location and put on a shirt and some shorts. My eyes wandered across Lori's room. Neutral colored walls and random decorative features on the furniture and walls. However, her bed was not all that big. Probably a queen sized mattress. Plenty big for one person or two lovers, but not for a single woman and her 19 year old babysitter. In mid thought Lori emerged from the bathroom. She had removed her makeup and now wore a robe. This wasn't the big fluffy hotel robe. No this was a pink "covering" that didn't cover all that much. It went down to just past her round ass. The material was more or less see through. The tie was around her up near her naval, but open up top all the way down to just before her belly button. It showed off her flawless neck into her chest, and the insides of her breasts, along with some of her flat belly below her breasts. After the tie the "robe" parted showing off her black lace panties. I handed her the wine as she walked past me. She took the wine saying, "Thank you sweetie." Continuing to her side of the bed I got a good look at her panty clad ass as she pulled back the sheets. "Get in the bed Jim. I won't bite." I got up from the chair and walked to my side of the bed. I took off my shirt but left on my shorts. I was attempting to hide my growing erection. I was about to slide into the bed when Lori said, "Take off your shorts honey. These sheets feel great on your skin." I looked up and realized she had taken her own advice. Her "robe" was hanging on a hook beside her bed, and she had slithered under the sheets without me knowing, and she was topless. I quickly maneuvered off my shorts and slid into the bed trying to hide my erection. "Oh Jim, could you get the lights?" "Sure." I responded. The only problem was my hard dick. If I stood it straight up and put it in my waistband it would stick out at least an inch. If I put it down a leg it would easily draw attention in my flimsy and short boxers. I was screwed. "I'm gonna go get some water want anything?" If I walked straight out of the room she would only see my backside. Threat avoided. Until she answered. "Actually yes I do, but you wouldn't know where it is. I will come get it." She got out of bed and put on her robe facing away from me. All that I saw was her smooth back that tapered into her nice ass and shapely hips. I couldn't stop oogling at her perfect body. I began to walk to the kitchen. A few steps out of the room Lori had caught up and she grabbed my hand. "My contacts are out. Don't let me run into anything." We walked to the kitchen. The lights were still off, but the moonlight was coming through the open windows and there was a glow from the display on the freezer. I fetched a cup and gulped down some water while giving my cock an "un-pep" talk. That became difficult when I looked up and saw Lori struggling to get a bottle of wine out of the wine fridge hidden in the cabinet. At 5'8 I towered over her, "Need some help?" "More than you know." She quickly responded. Lori stepped back and let me move to the counter. "Which one do you want?" Lori moved forward and placed a hand on my back and one on my waist. Good thing I didn't put my cock in the waistband. "It's the top right one." But she was more worried about feeling up my stomach and back. "This is the good stuff." I wasn't sure if she was talking about the wine or my body. I retrieved the bottle, shut the cabinet and poured Lori another glass of wine. We headed back to the bedroom in her near blind and tipsy state. By this time it was 4:00. We talked for another hour or so and I made 4 more wine runs in that time. We had talked about my school, her kids, her job, and my future. I returner after the 5th wine run this would be her 7th glass plus whatever she had at dinner. As I sat down Lori asked me another question, "So Jim do you have a girlfriend?" I knew the question was inevitable. "I did. We broke up 3 weeks ago. I am at the age where I am looking for a wife. Not a girlfriend." "Are you a virgin?" 7+ glasses of wine on a lightweight like her had loosened up the conversation I guess. "No I'm not." "How many girls have you gone all the way with?" "Two." "Tell me about them. Tell me about the sex!" Over the last five glasses of wine she had sat up in bed exposing her breasts. Which I learned during glass 5 had been augmented from a B to a C only a few months ago. (They looked perfect and their was almost no scarring) "Well I lost my virginity to a girl I dated for about 2 months. She was a virgin as well. I knew her in High School and really liked her company. She has small boobs, but she had a killer body. She plays soccer, our first time was in my bed. She stayed the night when my family was out of town. We didn't fuck though. We made love. I thought she was the one." "Then why did y'all break up?" "She was going to school on a partial scholarship. Academic and athletic though. She got an offer to play for North Carolina. She's a great soccer player and that's one of the best schools in womens soccer. We decided to break it off before it got "serious". We had sex so to me it was serious. We actually kept up a purely sexual relationship until about June, but at that point it wasn't making love any more. We were just neutralizing our teenage hormones. So we started dating in March, broke up in in mid May and fucked til late June." "That's so sad." She says as a tear dropped down her face. The wine was making her emotional. "What about the second girl?" "It was mistake. I knew her from college. She is a waitress at Hooters. I was out with some friends one night. Boys and girls. Someone had invited her. We were going to do a movie marathon together. You know like 5 movies in a row? Well after the second movie we went out to my truck and banged it out. After feeling each other up for 2 movies we were both horny. I hadn't fucked in a week and she was a slut. With the first girl we had bare sex. She was on the pill and we were in love, but with the second girl I always used a condom. She was on the pill too, but she had been with tons of guys. We said we were dating, but we were just fuck buddies. She was great at that though. She had nice big boobs bleached blonde hair and a perfect. We knew it wasn't going anywhere. We were both mature enough to see that we were only horny." I'm pretty sure Lori was fingering herself or at least playing with her clit. "Why did y'all stop?" "Like I said it was three weeks ago. I started chasing another girl that was more "wife material". It was only a matter of time until that slut gave me an STD anyway. I actually have a date with that new girl tomorrow night, well I guess that's tonight now. Being that it's 6:00 am." We had talked for over three hours. Topics ranging from kids to sex. Lori said, "I am going to try and get some sleep before the kids wake up. Thanks for staying tonight Jim. I have enjoyed being with a manly man that is also handsome and caring. They don't make guys like you anymore." She slid down into the bed, finally covering her nice tits. I fell asleep soon after. I woke up at about 9:00 am to Lori rubbing her ass against my morning wood. I don't think Lori even knew what she was doing. Lori began to stir after I made some loud noises so that she would get off my dick. After only a few minutes Lori's body jumped, "Jim, I'm so sorry. I didn't mean to make you feel you up like that." "It's no problem we're both adults. We can handle some contact." I said as she turned towards me and started running her hand up and down my rock hard shaft. She seemed to have sobered up over the last few hours and she appeared more sure of her actions. "Jim, like I keep saying. We are both adults with no other person in our lives. Are you ok with where this is going?" "It depends. Are you looking for sex or a relationship?" "Relationship. I'm only in my early forties. I can still have kids and make a man hard. I want to find a man." "Consider him found. Lori do you have any plans next Friday night?" "No I don't." "Then I will pick you up around 8?" "Sounds good. What about right now?" "How about we save it for Friday night? That ok Lori?" "No, but I'll make it. What about this other girl that you have a date with tonight?" "I'm going to give it my all. If things work out then great, but if things work out between you and me then.... I'm yours." She replied, "Sounds good Jim." She released her hand from my cloth covered cock and got out of bed. She put on her glasses and walked to her bathroom. Topless. Friday can't come soon enough. A Unique Relationship Ch. 01 Chapter 01: Living With a MILF If you haven't read the prologue yet I suggest you do. I admired myself in the mirror. Ready for my date. My name is Jim and I am a 6'4" college student. At age 19 I have almost washboard abs and large toned muscles. To top it all off I am about to go on a date with a 41 year old single MILF. ----------------------------- We had dinner at the nicest restaurant I could think of. Money was not an issue for me, or Lori. She was so easy to talk to, and so beautiful. She wore a black dress. Not a tight one though. It hugged her breasts but was wider around the bottom. It reached to just above her knees. Her 34C tits looked amazing, and I was looking forward to the night ahead of us. Her kids were staying this Friday night with their grandparents. Lori told them she was going on a date and her babysitter was unavailable. That's because I was her babysitter. Since I still lived at home, about to start my Sophomore year of college, I told my parents Lori needed me to babysit over night. -------------------------- We arrived back at Lori's house. We walked in holding hands. We walked directly to her bedroom. "Jim, are you sure about this?" I didn't answer I just began to kiss her on the lips. A sensual soul rattling lip lock ensued. Our tongues were writhing against each others lips trying to fight for entrance. Our tongues swirled together taking in the taste of each others mouths. I ran my tongue across her beautiful straight and white teeth. Our hands roamed up and down each others bodies. I latched my hands on her ass and picked her up. She wrapped her legs around me never breaking the kiss. I laid her on her back on the bed. She began to unbutton my shirt, soon throwing it into the corner. I reached my hands behind me and removed her heels. We detached for only a moment. I stood facing the bed and Lori was on her back directly in front of me. I pulled her up so she was on her knees. I grabbed the bottom of her dress and pulled it over her head, revealing her matching black lace bra and panties. Along with her flat stomach and toned legs. Next I stepped out of my shoes and socks while Lori unbuttoned my pants and dropped them to the floor. I stepped one leg out of them and kicked them to the corner. I was standing there hard in my boxers. My toned muscles on display for Lori who was standing on her knees in her bra and panties. I basically tackled her onto her back. We began kissing again, this time our skin was touching for the first time. My hands grabbed her perky bra covered breasts. I could see her areola through the lace. I removed the front clasp releasing her perfectly shaped melons to my bare hands. I had seen her breasts only a week ago, but touching them was tantalizing. We rolled onto my back. Lori sat up on her knees between my legs and used both of her hands, and a little help from me, to pull off my boxers. Leaving me nude and exposing my 8 inch stick to this hot MILF. She grabbed my cock and laid it flat against my pelvis, the head reaching past my belly button. She held it there and placed her tongue on my asshole. Then licking it all the way up over my balls and to the head. Lori licked up the glob of pre cum off of my belly before she took the head of my cock in her mouth. I gasped in surprise and pleasure. I let out a deep moan as Lori engulfed my entire 8 inches. Her lips were kissing my trimmed pubic hair. I would've said "Wow," or something, but we were beyond words now. The only sounds were my moans of pleasure and the sloshing of my dick down Lori's throat. She played with my balls and tickled my asshole the entirety of the blowjob. I felt the cum stirring as my balls tightened. Four weeks of pent up semen was about to go down Lori's throat. However, she pulled off before I came. She put her body on top of mine and gave me a kiss. My hard dick was standing straight up between her thighs rubbing against her lace covered pussy. The ball was in my court now as I continued kissing Lori I rolled us back onto her back. My goal is to make a woman orgasm once before intercourse. Unless we were just fucking, but this was love making. I gave one final thrust into her lips. I kissed her on the forehead, nose, mouth again, then chin. I leaned up and nibbled each earlobe tracing my tongue over her face between ears. I sucked the outline of her collarbone. I then traced my tongue along her side, down to her waist, across her panty line to her hip bone and back up her side completing a box around her torso. One last line down the center of her chest between her breasts, and making a pit stop at her belly button before running my tongue over her panty clad mound. I placed a kiss on her pussy and got off the bed. There was a look of fear in my lover's eyes when I stood up, I believe she feared it was over. On the contrary, I grabbed her legs and pulled her towards me until her pussy was on the edge of the bed. I leaned forward to kiss her thus rubbing my penis against her covered treasures. I leaned in but stopped before our lips met, teasing her. I moved down to her fabulous breasts. They sat perky on her chest, I licked around each breast and around each areola without touching the areola or her hard nipples. Then I removed her panties. Her labia lips had parted slightly at her arousal showing off her pink insides. Her clit was begging for attention. Her pussy was completely shaved. I leaned towards her pussy and exhaled slowly. This made Lori's skin become covered in goose bumps. I proceeded to cover every inch of her legs with kisses. Starting with her left foot to her left knee. I stopped and repeated the process on her right leg. I then started covering her thighs. Left leg then right leg. I kissed around her pussy, then I place a kiss right on it. After all this teasing her pussy was dripping wet, Lori was panting, and I was about to give her the best orgasm of her life. I leaned forward and began kissing my lover. Our tongues clashed as we sucked on each others lips. While we were doing that my hand inserted two fingers into her well lubricated vagina. Her hands grabbed my back trying to do something to express the pleasure. If we had not been kissing I'm positive she would've yelled. I slowly started maneuvering down her body. This time I wasn't teasing her though. I took one boob in my mouth. Grabbing her other boob with one hand while my other hand tried to find her G-spot. I thought that her nipples were already hard, but after a thorough tongue lashing they were standing taller. I continued my journey south. Once I reached her pussy I attacked her clit with my mouth. I did everything from sucking to toying with it. This sent Lori into her first orgasm of the night. All the teasing had built up and the pleasure I allowed her to feel made her pussy gush juices onto my fingers and all over the bed. I then started to eat her pussy as she came down from her orgasm. Each hand went up to one breast and began to pinch, rub, and molest each breast. My mouth was going to work on her wet lips. Between that and the pleasure my hands were giving her tits she started her second orgasm. This time my mouth was there to gather anything that trickled out. Lori's hands on the back of my head and her thighs clamped over my ears assured I would thoroughly clean her up. Other than the moans we had not talked for a while. Lori broke the silence saying, "That was great Jim." "I actually enjoyed it too." "I'm ready for the main course now." "Condom?" "Nope." That got my 8 inch rod harder and thicker than ever. If we were just fucking I would have just started going at it, but we were more than that. I leaned forward and took her lips into my mouth letting Lori taste herself on my tongue. Now we were ready, Lori was on her back. I repositioned her so that she was in the center of the bed. I mounted her missionary position I rubbed my penis up and down her slick entrance. I then pushed in only slowly until my hips met hers. Here we were joined together. Her silky pussy was wrapped around my cock. The room was completely silent other than our labored breathing. I slowly unsheathed my cock from her drenched love tunnel until only the head was still connecting us, then I slowly inserted it again. And out, and in, and out, and in, and out, and in. Slowly. I kept that up for a solid amount of time, which is impressive considering how much I wanted to pound this hot MILF of mine. I pulled all the way out and laid down on my back. Lori got the hint instantly and straddled me. Lori positioned herself above my cock and impaled herself on it. All the way down. She then leaned her body over me, and laying chest to chest we, once again, started kissing. Her ass continued to dance up and down, sliding over my rigid shaft and back down. I had my hands on her ass and Lori's hands were running a muck in my medium length brown hair. I let out a moan of extreme pleasure and Lori began to do the most pleasure inducing thing ever. She started contracting her vaginal muscles while I was inside her. It gave the feeling of a constricting pussy during orgasm, but she was still going. I broke the silence barely working out, "I'm... abou.... cum!" Lori impaled herself onto me once more then stayed completely still. At this point all that my mind was saying was baseball, grandmas, hairy men. I was on the edge of orgasm but not ready yet. After a solid 2 minutes Lori got off of my still hard cock and got on all 4s. Sweet. I positioned myself behind her and grabbed her ankles, yanking them out from underneath her. Thus, she was flat on her stomach. I rested my cock between those two toned mounds also known as butt cheeks. I leaned up and grabbed her hair as if I was putting it in a ponytail. Holding it in one hand off to the left I trailed kisses across her jaw line and nibbled her earlobe. I switched sides and did it again. I placed a kiss in the center of her neck then placed her hair gently to the left and whispered in her right ear as if trying to hide our words from someone. "You ready for my big cock?" "I am sooo ready for your big cock you handsome young stud. Take me." That's what I was planning on. I pulled her legs so that her legs were in a "V" shape as she laid on her stomach. I placed my cock at her entrance and forcefully inserted half of my cock. I continued my half cock thrust until she started moaning. Then I knew it was time, I began to ram my cock all of the way into her surprisingly tight MILF pussy. I gave her a solid swat on the ass. Almost as if that was an "on" button she began to orgasm for the third time. Her hands waved around trying to grab onto something. My thrusting continued sending slight ripples through her toned ass cheeks. I licked my finger and shoved two up her ass, thus sending her into another explosive orgasm. I removed my cock and flipped her onto her back again. My cock quickly reconnected with it's new friend and I kept pounding away through her orgasm. She wrapped her legs around my back and her hands finally found a grabbing point on my upper back. My lover was holding us close as I approached orgasm. After the last hour of sex and the blowjob and the 4+ weeks since an orgasm I could tell the load would be big. I contemplated not telling her of my impending orgasm as I continued my penal onslaught of her vagina. Considering the last two times I got close she made me stop. She was at like four orgasms already so I switched my thrusts to 6th gear and she exclaimed her pleasure to the heavens. "Dammit, uh... Lori I'm cumming!" "Uh, Uh, Uh, no pull out." Too late. My orgasm ran trough my body igniting another gear as I somehow (teenage hormones) kept thrusting into her pussy. As my cock never deflated Lori began her final orgasm of the night. -------------------------- We lay connected at the pelvis for many minutes. My dick never went soft and I was ready to go at it again. "That was the best sex I've ever had Jim. You really know how to please a woman, and not just with your cock, and thanks for pulling out on such short notice." I rolled off of her and looked into her beautiful eyes, "I didn't pull out in time." "What?" She reached down and cupped her pussy. She looked at her cum coated hand. "I'm going to start ovulating tomorrow." "Dammit." A Unique Relationship Ch. 02 Chapter 02: A Unique Relationship I woke up and looked around for my phone. I found it on Lori's side of the bed. It was 10:00 am. I already had 10 texts from Lori and 3 missed calls. Let me fill in the blanks of why I awoke in Lori's bed. After the first night we made love Lori offered me the position as a "full-time nanny," which is why I am living at her house. I really don't work though. I have basically been her fuck buddy for the last 6 weeks since our first night together. She cooks dinner, cleans the house (whatever the maid doesn't clean), and we have sex. Well oral sex at least. I may have made Lori pregnant. The first, and only, time we had sex she told me no condom, and then told me to pull out after I was already cumming. Since then it's just been blow jobs. But I'm not complaining. Her texts are probably about the doctors visit she had this morning. It's been 6 weeks since the possible conception and all tests have been negative, she started birth control the week after our scare. So either she is pregnant or the birth control stopped her period. I looked down at my phone to end the suspense, but all the messages said call me. They were 30 minutes old so I figured I was in trouble. I slide my icon across the screen automatically calling her back. Aaaaand ring, ring, ring, "Hello?" "Hey baby, so sorry I didn't get your messages." "It's no problem, I'm pulling in the garage now. Come out here. I have a surprise for you." Dammit. A "surprise" I'm too young for this. I'm only in my second year of college and my girlfriend who is 20 years older than me is probably pregnant. Ugh. I walked into the garage as she put the car in park. Today she was driving her "mom" car not her "sexy MILF car" as I called it. (An Expedition and a Mercedes she bought 2 weeks ago) She stepped out of the car in her white short short short shorts and black tank top that showed her cleavage and some bra side boob. I kissed her on the forehead and said, "Good morning sweetie." "Hey stud." "So?" "So what?" "Dammit, Lori, are you pregnant?" "I was going to let you fuck me, but I'm not so sure now." "So if we can fuck that means you're not pregnant?" "Nope." I breathed a sigh if relief and Lori said, "I bet you're hungry." "I am." Lori walked into the kitchen and began to make breakfast. Nothing major she had already eaten. I went to the bathroom to get ready for the day. I had a scruffy beard going on, but Lori said she liked it. Especially when I kissed her or ate out her pussy. I put on deodorant and cologne and combed my hair. I walked up behind Lori, and I was completely naked. I pressed my boner right up against her taut ass and wrapped my arms around her grabbing her breasts. All the blowjobs in the world can't take your mind off 6 weeks of no warm pussy around your cock. "Jim, aren't you going to eat first? I made you breakfast." I didn't answer. I grabbed the bottom of her tank top and pulled it over her head exposing her large bra encased tits. Next I unbuttoned her barely there shorts and dropped them to the ground. After that came the bra. Out popped her marvelous mounds of mammaries. Only a slight sag due to the post divorce boob job, but hey. I wasn't complaining. Lastly, off with her panties. Now both of us standing in the kitchen completely nude I spun Lori towards me and picked her up. No time for foreplay I needed to fuck my lovely girlfriend. She wrapped her arms around my neck as I aimed my cock at her pregnancy protected, and unusually hairy pussy. My cock began to slide in thanks to gravity, well I guess she was really sliding "on." With my hands on her ass I picked her up a little then dropped her and slammed my dick into her pussy. Once I was completely in I did it again, and again, and again. Our bodies were slapping together. Pretty soon my arms got tired so I put Lori on the floor. Turned her around and bent her over the kitchen counter. We fucked as I slammed into her pussy. I was holding her boobs and playing with her nipples. Leaning up I could place kisses on her back and neck. I reached onto the counter and retrieved the grape jelly that was out. I used my hands and pulled out a large amount. I split it between my hands and I rubbed it onto Lori's swaying boobs. Her nipples became even harder from the cold substance. She began toying with her clit and her pussy started convulsing around my cock as she began her orgasm. As I continued to thrust I was also trying not to climax yet. Lori came down from her orgasm and disconnected herself from me. Turning towards me I could see her jelly covered tits. I leaned down to clean one up and Lori placed her hands on my head and pulled me into her breasts. I got some of the jelly cleaned up, but a lot of it ended up on my face. After cleaning off both of her breasts Lori suggested, "Let's go shower. You can come with me so we can take care of this," she was referring to my penis and she used it like a leash pulling me to the master bathroom. We arrived and my hot MILF girlfriend started the water in the big walk in shower. "Lori, what do you think about going out tonight?" "What day is today? Friday, yes! I can take the kids to their grandparents house and we can go out." "Awesome. I think it's appropriate to celebrate." "Of course!" The water wasn't warm yet and we continued talking and I came up with an idea. "How about I drop you and the kids off at your parents house and you can get ready there then I can pick you up later like it really is a date." Lori contemplated and then answered, "Ok, but does that mean that you are going to take me back to your house and fuck me?" "I hope." I replied pulling her close and giving her a hard kiss on the lips. "We will see, but for now let's shower." We stepped in and took turns rinsing off. We soaped each other up and then gave each other a final rinse. Then Lori turned off the water and grabbed a towel. I said, "What about this?" Pointing at my still stiff rod. "I don't have sex on a date until the guy has bought me dinner." "That's not cool." She dried off and pulled out the hair straightener and blow drier with a noticeable smirk on her lips. I walked to the guest room which is where I was really supposed to be staying, but I slept with Lori every night. I grabbed some athletic shorts and a t-shirt. Since I had been living with Lori I've had nothing to do except have sexual relations with Lori, sleep, play video games, and work out. I only attended class Monday through Wednesday so I have stayed in shape and put on some serious muscle (Lori liked my body more every day, and that's what I was aiming for). So after getting dressed I went out to the garage to lift weights. ------------------------- I lifted for an hour then ran 3 miles. Even though it was Late September it was still a hot and humid day under the Texas sun. I grabbed some of my post workout protein stuff out of the fridge and went about my normal post run routine of going through the gate to the backyard and swimming some laps to cool off and cool down my muscles after the workout. I entered the backyard and saw Lori tanning. Nude. This was not unusual, but she never let me finish earlier so I got pretty hard pretty fast. I stripped off my clothes exposing my hard dick (There was a 10 foot privacy fence so good luck seeing us). "Hey Jim! Come here for a minute." I walked over to my naked girlfriend my hard on leading the way, "could you put some tanning oil on me?" "Sure." This wasn't out of the ordinary either, but I usually got a blow job in the pool or we would 69. The date tonight was costing me a lot of pussy. I squirted some oil onto my hands and started applying it to her toned body (she worked out a little also). She was laying on her stomach so I made sure to get a good feel of her ass and to rub up against her pussy. She flipped over and her eyes were closed. This time I aimed to give her pleasure since she was taunting my by doing this. I massaged her breasts and toyed with her nipples. My other hand worked the oil into the folds of her pussy. I massaged her body with my strong hands and soon Lori was reaching down to masturbate. I grabbed her hand and said, "I don't let my girlfriends masturbate in front of me until I've bought them dinner." The rest of the day consisted of us teasing each other. We both walked around naked. I sported an erection the entire day and Lori made sure to spread her legs whenever she sat down. ------------------------ I dropped Lori and her kids off at her parents house around 5. I was picking Lori back up at 9. Alone at Lori's house I had a good amount of setup to do for that night. Lori thought we were going to have a nice dinner at a restaurant, then fuck each others brains out, but in reality I had other plans. At least for the dinner part. First I started cooking Lori's favorite dinner. As it cooked I went to the shower and shaved my pubic hair bare like Lori liked it. I got a nice shirt and some pants out of the closet. I got dressed fixed my hair, deodorant, cologne, and shoes. Damn I looked good. No wonder I had a MILF hungry for my dick. ------------------------ I picked Lori up at 9. I made her sit in the back of my truck blind folded. "Where are we going Jim?" "You'll see baby." "Ugh. Ok. So how are things with you and Ashley?" That was a weird subject. Obviously I was living and "dating" Lori, but I also had a girlfriend my age as well. Lori knew about Ashley and she was fine with it. Lori knew we couldn't really have a future together. She was double my age and already had kids. Ashley was my age and absolutely perfect. "Well we are still together." I resumed. "That's wonderful. Have you two had sex yet?" "No, she is a virgin and very conservative. Eh, well not necessarily conservative just not an easy girl. Which is great." "That's great for you two. If things get serious between you two let me know and we can break off our thing." "What is our status Lori?" "Friends with benefits and maybe future couple." "I like the benefits part." "Me too Jim." ------------------- A few minutes later we were at her house. I kept her blind folded and she had no idea where we were. We followed the path from the driveway to the pool. I had a candle lit dinner set up on the table. Wine chilled in a bucket and dinner in the oven. I took off her blind fold and she gasped at the sight holding her hands over her mouth. "Jim! This is the most romantic thing that anybody has ever done for me." We embraced in a hug and I kissed her on the forehead. "So can we update our status Lori?" With tears in her eyes she replied, "Yes we can," sniffling she finished, "we can change it to dating." Hell yes! A Unique Relationship Ch. 03 Chapter 03 A Unique Relationship We finished up dinner and I admired Lori. Her sandy blonde hair cascaded over her shoulders, and she wore a yellow dress that buttoned all the way down the front. It reached just past her ass. She was wearing black leggings and showing some nice cleavage. Candle lit dinner under the stars, and Lori loved it. "So Lori, are we seriously a couple now?" "I think so, don't break off things with that girl your age, but I'd like to be yours." I stood up and went to Lori's side. I extended an arm and said, "May I have this dance?" Lori looked surprised until I reached into my back pocket and pressed the remote control turning on the music. With a tear in her eye she said, "Yes." She stood up and I held her close. She sobbed into my comforting body. I guess after getting divorced from your "soulmate" after 15 years of marriage finding love again is emotional. We danced around the pool under the moon for countless songs. I placed kisses on Lori's head taking in the aroma of her hair, the feel of her skin, and the presence of her body. We pulled apart after the playlist ended. With her arms around my elbows and my hands still extended to her waist we stared into each others eyes. "Jim, you are the most romantic guy that I have ever dated, or even known. Even though we've only been on two dates I feel that we are close. We live together and with the whole pregnancy scare I feel that we have been through a lot already..." I cut her off saying, "I love you too Lori." "I love you Jim." With those words our lips met. I grabbed her ass cheeks and tried to pull her as close as I could to me. Her hands grasped the back of my head, her fingers intertwined in my hair. We pulled lips apart, but still our foreheads touched. I looked into her beautiful green eyes that sparkled in the glow of the night. We pulled apart not knowing what the next step was. Lori, being a mom and a housewife, began to clean up dinner. I knew I couldn't let this magical moment pass. "Leave the dishes there. Let's go get ready for bed." She dropped the dishes and I grabbed her hand leading her into the house. After a pit stop in the kitchen for Lori to get more wine we headed into the master bathroom. I began to undress Lori. First taking off her shoes. Then I began to unbutton her short dress type things. Revealing her braless breasts. I tool each nipple into my mouth for a moment making them stand at attention. Next I began to remove her leggings and panties. I embraced Lori in a kiss and cupped her hairless mound. Then she began to undress me. Starting with my shirt button by button until she expose my hairless and muscular chest. Taking the shirt off of my arms she exposed my toned muscles on my arms. After that was my shoes and pants. Leaving me in my boxers. She placed kisses across my body that she loved so much, eventually reaching the waistband of my boxers. She grabbed the waistband with two hands and pulled them to the floor as she went to her knees. I reached back and started the bath water as she tool my semi hard cock in to her hand. She pulled it up and licked at my balls until I was completely rigid in her hand. Then she stopped and motioned me towards the tub. I got in and she straddled my lap, facing towards me. We made out as her hard nipples rubbed against my body and I cupped each of her ass cheeks with one of my large hands. My cock was lodged in-between her ass cheeks still hard as a rock. I slid my hands down and began to finger her pussy. She began to moan from deep within. Not some high pitched porn star moan (which I find annoying), but a sensual moan that was second nature because of the intense pleasure that her body was feeling (which I find hot). With both of my hands around her pussy I continued fingering her pussy with one hand and her ass with the other. Meanwhile my thumb was toying with her clit. After only a few minutes of that her body began to shake as she was cumming for the second time that day. Her pussy and ass clenched my fingers and her hands clawed at my back. After an intense orgasm she collapsed on my chest. She came to a minute later and said, "Jim that was incredible. I keep thinking you can't top yourself, but then you do." "I love to see the woman I love get the pleasure she deserves." "Well I think it's time the man I love gets what he has been waiting 6 weeks for." She reached between us and grabbed my cock from underwater. She hoisted herself up and then impaled her tight pussy onto my throbbing erection. I have missed having a warm pussy around my cock. The sex earlier today wasn't long and it had been 6 weeks before that since our pregnancy scare started. Now I could finally go 100% with my lovely woman. She was on the pill, slightly tipsy from the wine at dinner, and horny as hell. Lori slowly went up and down slipping my cock in and out of her lovely pussy. She was riding my cock smoothly and sensually. Her constant strokes made my cock completely rigid. After a while of Lori riding my cock she leaned in for a kiss as said, "I love you Jim." "I love you too, Lori." I took a mental step back and surveyed my life. I was currently in the bathtub with this MILF with sandy blonde hair, absolutely perfect tits, and smooth toned skin. "Get on all fours Lori." "Whatever you say baby." After some fidgeting we managed to get her on all fours and my cock positioned at her pussy. I grabbed her hips and continued making love to my beautiful.... girlfriend? This was sensual sex, not "I'm gonna make you sore sex." We were determined to just show our love to each other like this. Take our time. No matter how slow we went I had a pretty big orgasm on the way. Lori was rubbing her clit on this position as I continued to massage the insides of her soft and tight pussy with my cock. "Lori I'm about to cum." "Me tooooo.... Ah." Lori started to orgasm and I stuck a finger up her ass which made her body convulse even more. Lori lost all her strength and went headfirst into the water. I pulled her up until she regained her strength. I was no longer on the edge of orgasm by then, but my cock was still hard. I sat back in the tub and Lori sat on my lap facing away from me. My cock was at an awkward angle until it pushed its way into her pussy again. I whispered in Lori's ear, "I guess they can't get enough." Referring to our sexual organs. "Neither can I." Lori raised herself a few inches off of me so that I could thrust into her. I fondled a boob in each hand as we continued to make love. "Lori I'm getting close again. Where do you want it." "Put your cum inside me." After another minute I reached that point. One final thrust deep into her pussy, slamming my head all the way in I started to cum, during sex, for the first time in six weeks. The release felt wonderful and Lori moaned in pleasure as well as my hot liquid soothed her insides. We lay there for quite some time. Lori sitting on top of my my softening cock still inside her. Eventually my cock popped out of her and my semen began to float around the tub. That was my queue to get out of the bathtub. I stepped in the shower and began to wash off. I suddenly I felt two tits press against my back and two arms around my torso. "Jim, I am so happy that this happened. I love you for so many reasons. You are funny and handsome. Very romantic and caring. Plus you are better in bed than any man or woman I have ever been with." Wait woman? I responded by turning around and putting each of my hands behind her head and smashing our lips together. "I love you Lori. Our age difference really doesn't matter. You are the perfect girl for me and I will never let you go." ------------------------- We finished washing off then got in bed around 12:30. We made love until 9:00am though. Every position, oral, and I even got a handjob. We got out of bed at 9:30 and showered, but we didn't get out until Lori gave me a blowjob. Then I banged Lori missionary on her closet floor. We got dressed to go pick up the kids and we stopped on the side of the road and Lori rode me in the backseat of my truck. We picked up the kids and stopped at a restaurant to eat. Lori and I both excused ourselves to the bathroom where I pulled up Lori's dress and took her while she was bent over the sink. We got home exhausted. We hadn't slept in over 30 hours and we've been having sex for most of the last 12 of those hours. Lori even gave me a handjob while we were taking to her parents at the table, and she gave me one at lunch. By the time we went to sleep, not before we made love three more times, I had cum 13 times in the last 24 hours and Lori was at 21 orgasms. We were both kind if horny. ------------------------ It was only late September and we had been living together for only four weeks. We loved each other, but I had another girlfriend my age. What was I supposed to do, I loved both of these women.