Dating My Friend’s Single Mom

This is the true story of how I fell in love with my friends mom.

Part 1: Background and Meeting Rachel

Hello I'm Rick and this is the story of me falling in love with my friend's hot mom. I met Rachel when I was a freshman in college. She was the mom of my roommate Mike. Mike and me went to a military college and met as our families were all moving us in. She raised Mike as single mom and when we met I'll never forget the butterflies I had as she hugged me and we made eye contact.

As college progressed, I become close with Mike and we roomed together all 4 years of college. Rachel had Mike at age 16 and his dad bolted shortly after he was born. Luckily, Rachel had amazing parents who helped her raise Mike and allowed her to finish college and get her teaching degree.

Throughout college I'd visit Mike, and Rachel would always be there looking stunning as ever. Then, she was in her mid-30s, with blonde hair, blue eyes, was about 5-4, always had her nails done, weighed 130 pounds, and had a nice perky butt with 34dd breast. Me being more of a morning person i'd often have coffee with Rachel as we got up way earlier than Mike. During those conversations she'd tell me about how she wanted to met a nice man or problems she was having with dating. Most men were her age but none of them ever seemed good enough for her.

I was lucky to find out my military service was delayed so I could go to law school and be a JAG for the Air Force. I was accepted into the law school in the same city where Mike was from. He commissioned right out of college and moved across the country after graduation. He told me while I did my 3 years of law school to help his mom if she ever needed anything. Boy was I in for the time of my life by helping her.

Part 2: Rachel and me Realize our Mutual Attraction for Each Other

After moving into my apartment near my law school that summer I got a call from Rachel. I had turned 22 that year and Rachel was 38. She was a third grade teacher and had just broken up with her then boyfriend of about three years. Rachel needed help setting up her classroom and asked if I could assist. Without any hesitation I said of course.

That Saturday, I went to Rachel's classroom and helped her organize her classroom, hang up posters, and put her future students name plates on their desk. During that time we both realized we had a lot in common like running, cooking, traveling, and watching football. I asked her if she wanted to go running with me that next day and if we burn enough calories get a cup of coffee after. She smiled and said "sure haha. It'll be a date!" without thinking much of it I said let's meet at the park near my apartment the next day.

The run went amazing as we talked about traveling, our past relationships, how we like dogs, and even joked about what the best ice cream flavors were.

Now I wasn't the biggest player in college but I had a decent amount of experience. I had two girlfriends who I had sex with; plus a few drunk hookups. At that time, I thought I knew what good sex was like but Rachel would change that for me!

After the run we went to grab a cup of coffee and all we could do was laugh and talk with each other. I realized how much fun the two of us were having and thought maybe we should hang out sometime! The feeling must have been mutual because when I asked Rachel if she had any plans for the next weekend she was so quick to say no and that she would love to dress up and have some fun! We agreed to hang out and I realized I had just asked my friend's mom on a date and she said yes!

Part 3: First Date

That next week building up to our Friday night date Rachel and me texted pretty regularly. The text were not overly dirty but they were flirty and we kept saying we couldn't wait to see each other again!

That Friday Rachel and me met at the local mini-golf course. Before we played Rachel said let's make this interesting if you win name what you want! I responded with a laugh and she gave me this coy smile that made me shake with excitement. I said well what if you win...she twirled her hair and said you'll buy me a bottle of wine after. Rachel went on to easily beat me that round and we went to a local new hip restaurant. There I bought Rachel the bottle of Syrah wine which we split. The conversation turned a little more sexual and we talked about how many people we'd been with. To my surprise Rachel had only had sex with 4 guys in her life. The most resent being her ex, but it really wasn't that good. I told her my experiences. I asked her if she was more of a giver or receiver! She said that's easy I love being a giver! The night went on and as we got closer to fishing our bottle our hands interlocked! I couldn't believe I was holding hands with Mike's hot mom! When we finished Rachel said she was tired and was ready to go home. I got up and gave her a quick kiss on her lips and said let me walk you home! She smiled and said okay sweetie! I led her out of the restaurant and right as we got outside she pulled me in for our first real kiss! We made out in front of the restaurant and our tongues started going in each other's mouths. We did this for about a minute and when I broke the kiss we both were so giddy!

I walked Rachel home that evening and we held hands the whole way. Every-time we stopped at a light we kissed. When we finally got to her house she said let's hang out tomorrow! I said well I have plans in the afternoon but do you want to grab drinks? She said "it'll be worth your while!"

Part 4: Getting More Intimate

The next day Rachel and me met at a local brewery and picked up right where we left off. Rachel had just had her nails done (pink) that day, had curled her blonde hair, and wore the cutest black dress!

We split a pitcher but halfway through we realized we wanted to be somewhere more private. We kept kissing and she started holding my hand and we each rubbed each other's leg. We ordered some shared appetizers since we were hungry, but ate those quickly, finished the pitcher and Rachel said your apartment is not far from here maybe let me go see it? I said sure thing!

We kissed so many times on the short walk to my apartment! By the time we got into my buildings elevator we started making out and my dick become so hard. Rachel said someone is excited and started rubbing my penis over my shorts.

When we got into my apartment we went right to my couch and she straddled me. We made out for 10 minutes with our tongues going down each others throats while she humped me. I undid the back of her dress and she rubbed her newly manicured pink nails over my chest. We flipped over and I was now on top of her. I started moving my way down to her breast and as I started kissing around her nipple she started to moan. I then took my fingers and started moving them down her stomach towards her vagina. I then teased around her panties and her moaning got quicker and louder. I then pulled her dress down and moved her panties away from her vagina. I rubbed the outside of it in circles and she said please Rick finger me. I listened and put my indix finger around the tip of her clit and did little circles. This made her scream out in joy - "Rick, Rick wow that feels so good...it's been so long!" I then moved farther down and put in my middle finger and moved it in and out. I was looking at Rachel's face in pure joy! She pulled me close and said to move faster. I felt her pussy begin to tighten and she said, "I'm close baby don't stop now!" Her pussy clenched up as she dug her nails into my back and said, "Rick I'm going to have an organism for the first time in awhile! She shook and I started to kiss her. When she finished we kept kissing and her hand started moving towards my leg!

She then broke the kiss and said I like it when my man cums in my mouth but you just have to give me a heads up! She then pulled me close for a kiss - and told me to sit down on the couch. She straddled me again and pushed me down so she was fully on top of me on my couch.

While we kept kissing she moved her hands around my penis and started to undo me belt and shorts. She pulled my belt all the way off and then my pants down. Rachel my buddies mom was now fully naked on top of me and begin to rub her pink nails on my balls and up the shaft my my dick. I don't know what she was doing but it felt amazing and I was so tingly. She then started to jack me off and rubbed her thumb on my mushroom! Next, she started to kiss my neck and whispered in my ear I'm going to please you so much baby. She then started kissing her way down my chest and stomach. My dick was rock hard with excitement!

She then did something I'd never experienced in my past blowjobs - she licked from the bottom to the top with her tongue and then came back up to make out with me while jacking me off. The saliva form her spit felt so good while she moved her hand up and down my shaft. After that, she went back down and put her right hand down on my shaft and started licking around the mushroom of my dick. We made eye contact and I loved seeing her head move up and down with her newly done pick nails jacking me off! I couldn't believe Rachel was actually giving me a blowjob! She then started licking down towards my balls and put the left one in her mouth and sucked it. She said "mmmmmm" and I was going crazy with pleasure! She licked from my balls up to the top of my dick and spit on the top of my dick. She then looked at me and said, "I'm going to deepthroat you Rick!" Did she ever! I was so turned on because she kept playing with my balls and I loved seeing her pink nails holding them while she fit the majority of my dick in her mouth. I could feel her tonsils on my dick and she never even gagged! After deepthroating me she stopped sucking and spit a little more on top of my shaft. She quickly returned her hand to the bottom of my dick and her mouth went back to the mushroom. Mmmmmmmmm was what I heard from her and I said Rachel I'm getting close! She started moving her hand and tongue quicker on my dick. "Rachel can I cum in your moth"....Mmmmhmmmm" is what she said! She then took her other hand and moved her nails up my stomach to my hand and we interlocked our fingers! My eyes started going into my head as I blew my load in Rachel's mouth. As I was cumming she kept going and it felt amazing. She even squeezed my hand tight and I swear it was a connection I'd never felt. No college girl had ever sucked me off like this before! Rachel then swallowed my cum and said that taste yummy compared to my ex Rick!

We cuddled up naked on my couch and fell asleep holding hands. We woke up and hour later and had some more blowjob fun. I came in her mouth again and she swallowed. After she said "well I can't spend the night yet baby but excited to have some more fun! I'm a freak for my boyfriends! Do you want to be mine?" Wow Rachel was asking me out and I would be a fool to say no! We planed to hang out at her house the next weekend!

Part 5: Sealing the Deal

The next week Rachel and me texted non-stop until our Friday night date. The messages were much dirtier now - she would tell my "how good I tasted and how she couldn't wait to feel my dick grow in her mouth." I told her "I want to taste her" and she said "I'm getting wet baby!"

We met near Rachel's house at a wine bar. She looked stunning in a blue dress, had straightened her hair, and her pink nails still looked fresh. The whole time we again held hands and rubbed our thumbs against each other. The sexual tension was building up and while we made eye contact we both couldn't wait to rip each other's clothes off and make love. We had a few glasses of wine, sandwiches, and even got some coffee so we had energy for the amazing love we were about to make.

After paying our eyes said it all. We both got up, laughed, and then shared a 10 second kiss. "Take me home Rick we need to go somewhere alone!"

We walked to Rachel's house and quickly went in. The moment she shut and locked her door we made out and her hands went up my shorts to my dick. She proceeded to rub her nails and thumb on my shaft and it feel so good. She then took her other hand undid my belt and dropped my shorts. "Rick you won't need your shorts or shirt until tomorrow! Take off your polo." I quickly did and she pushed me up against her door. She then licked my neck and nibbled on my ear. "Time to get you hard Rick." She dropped to her knees, looked up and smiled at me and proceeded to lick my dick from bottom to top. She took her right hand and ran her nails on my stomach. Next while maintaining eye contact she said do you want me to deepthroat you baby! I said please. She spit on my dick and put my whole shaft into her mouth! It felt so good and she continued to use her tongue around my shaft. I was in paradise from her amazing blowjob skills. She then came up, spit on my dick and proceeded to move her mouth between my mushroom and halfway down my dick while she jacked off the rest of it. "Mmmmmm mmmmm is what she kept saying" "Oh Rachel that feels amazing I'm so hard!" Her pink nails jacking me off looked so good!

Rachel continued to blow me for a good minute and she must have realized I was close because she said let's go into my room! I picked her up and we made out while I carried her to the room. Once there Rachel asked me to undo her dress and when I took it off I could tell she was excited! I kissed her again and laid her on her bed. Next I started rubbing my fingers around her vagina and her kissing got more intense. She broke the kiss and said do you want to go down on me!

I kissed on her neck first then made my way down to her tits and slowly licked her nipples. This must have drove her crazy with anticipation because she screamed oh Rick go down on my now baby! I did and she was so wet. I liked her vagina from the top to bottom and slowly started to to insert my tongue around her clit. Rick, my god this feels so good! Keep going baby while she ran her fingers through my hair. My tongue got quicker and she started to convulse and hump my face. Rick I'm so close keep going...Rick I'm cumming!! I felt her juices flow, and vagina tighten while she came!

Wow Rick! I made my way back up to her and we kissed. She said let me blow you some more Rick so you're nice and hard when we fuck! She had me move on my back while she got in between my legs and sucked my dick. Watching her head bob and pink nails move up and down on my dick made me get rock hard yet again! Rachel let's have sex! She made eye contact with me and said mmmmmmmm! She said let's start with missionary. I told her I had a condom but she said she wanted me to raw dog her!

I climbed on top of her and started rubbing my dick around her vagina. It was still wet from her saliva and I could tell she was excited as well. Please Rick put it in me! I slowly put my dick inside Rachel and couldn't believe I was having sex with my friend's mom. I moved my dick deeper inside her but was very slow. "Oh Rick this feels amazing! Yiu can go deeper of yoyd like" is what she said. We then kissed and I started moving a little quicker! She dug her nails into my back and her other hand was touching my face. When the kissing broke she said you're deep inside me Rick! Rachel felt so good and I was in heaven by how much fun we were having! "Faster Rick faster." I did and Rachel pulled me back in for more kissing! Next she said "I want to ride you." With me still inside her I put my hands on her butt and flipped us over! She instantly started riding me and I could tell I was balls deep inside Rachel!

"Fuck Rick you're so hard inside me I love it! Do you like your older girlfriend on top of you!" We then grasped each others hands and Rachel started ridding me quicker. "Fuck Rick you're amazing inside me!" She felt so wet and her pussy sliding up and down on my dick was the best feeling I had ever had. We started making out while still grasping each other. Rachel moaned in joy!

I then asked Rachel if she wanted to do doggy style. She said why not baby! She got off of me and said let me taste myself on you. She blew me for a quick 30 seconds and then got on all fours. I got behind her and she placed my dick back inside her wet pussy! Rachel was so wet it slid right in. "Fuck me Rick" and I started pounding her. I was going so fast and was so deep in her my balls were rubbing up against her butt. It was so hot! I knew I wasn't going to last much longer!

"Rachel I'm getting close where do you want me to cum?!" "Inside me Rick inside me! I can't get pregnant tonight so it's fine!"I didn't last more than 20 seconds after she told me due to the excitement of cumming inside her, and Rachel must have known. "Oh good Rachel I'm going to cum inside you!!!!" Rachel then turned her head around and we made eye contact as I came inside her. "Oh Rick feeling you cum feels so good, and warm as you finish in my pussy" while raising her eyebrows! I kept cumming and we kept our intimate eye contact! "Oh Rick I like your cum inside of me, feels so good!"

After cumming inside my friend's sexy mom, I kept my dick inside of her and humped a little more and saw my manhood oozing outside of Rachel's wet vagina. Then I collapsed into her arms and we kissed. She took her hand and ran her nails on my dick and it felt so good!

The rest of the night we made love 2 more times and Rachel let me cum inside her each time! Then we fell asleep with her in my arms - Rachel even gave an amazing blowjob the next morning, swallowed my cum, and made me an amazing cup of espresso. Hard to believe I was falling for my friends mom!

To be continued!