My best friends mom. Part 2: She wants to watch. [MFF] kind of.

A new week, a new chapter in the Best Friends Mom arc. In the last story I mentioned how my best friend Airin, hooked me up with her mom Lisa, because we both just went through bad break ups/divorce. So we went out to a bar where we danced, another where we kissed, then back to her apartment where we had the best sex I had ever had at that point in my life.

So what happened the next morning? We woke up together. We both agreed we’d have to do it again some day. She gave me a kiss and sent me away. The unfortunate part was having to do the walk of shame back home and see Airin.

As expected Airin was there with her girlfriend TJ. They’d been together for a while so we were close. That’s why I had no problem with her when she said, “Ah yes the walk of shame.” Airin and TJ sat on the couch when I came home and began the 100 questions. Going from “How was your date?” to “Where did you go?” And TJ with the question of the hour, “Did you fuck her?” But I simply said we had fun that’s all that they needed to know. Airin hugged me and said “Thanks for taking her out. She really needed it.” And with that my first encounter with Lisa was over.

A month later (April) was the second encounter.

I stated Lisa did a lot of outside projects. She did dance, yoga, and she had a side job as a hotel bartender. I got a call from her one night and she asked if I’d come by the bar for a drink.

When I got there she had just called for last call. I asked if I could get a vodka and she made my drink. At the same time she gave me my drink, I noticed this pretty blonde girl sitting at the other end. She had long hair that went down to her shoulders. Half was braided, half was straight. She wore a black dress, with a pair of black stockings and high heels. Lisa called out to her, “Angel honey. Last call you want anything else?” The girl looked up from her phone and saw me, “No L, I just had one so I’m okay.”

She went back to her phone and I asked Lisa about the girl. Her name was Angel she had been looking for new a place to have a drink. She had just moved to get away from her family and lived in a one bedroom loft nearby. Lisa brought me to the side and started whispering to me, “You think she’s cute don’t you?” Lisa had this way of knowing when I found someone attractive. She asked if I wanted her to talk to Angel and find out more about her. Lisa was the best wing woman.

Angel and Lisa started talking and occasionally looked my way. I smiled and finished my vodka and went over to them. She put out her hand “Hi, you must be MDW, I’m Angel.” Lisa went back to cleaning the bar and I began talking with Angel. I learned that she was relatively new to our area and the only job she could get so far was a local coffee spot. As we kept talking Lisa came back and asked if either of us had any plans. I didn’t have anything else to do and Angel said she planned on going back to her loft to sleep. Lisa suggested something that changed the whole evening. “Why don’t we all go back to my apartment? For drinks.” Anytime Lisa mentioned just drinks it meant she wanted to have some play time. Angel looked at us and said “Yeah lets go.”

Riding back to Lisa’s house was definitely a different experience. Angel had been drinking a little more and became more comfortable with us. At one point her and Lisa stared in each others eyes like they were about to kiss. Lisa had always been upfront about her attraction to people. Be it male or female. And I could tell she found Angel attractive. A familiar feeling washed over me as we all walked into her Lisa’s apartment. She took us to the kitchen and asked what we wanted to drink. She began pouring shots and asked Angel if she wanted to sit in the hot tub. Angel flashed her smile and nodded. “Lets go get you a bathing suit. But before we do I want to ask a favor.” Angel had finished her shot and said “Yes, anything.” Lisa walked from behind the bar and took my hand and put it onto Angels waist. Pulling us closer she said, “Will you kiss him?”

Angel looked at her and laughed softly as if to say really? She continued, “He is a very good kisser. And an amazing fuck.” At this point I didn’t know what to say but something changed in Angels eyes. She went from innocent to lustful in a matter of seconds. Her blue eyes were fixated on mine. “I will ask you again. Will you kiss him. Now.” It sounded more like a command than a question. Angel leaned in and kissed me. The longer we kissed the more turned on Lisa got. Angels lips felt amazing. I began running my hands all over her body and when we broke I could hear nervousness in her voice. “Wow.” was all she could say. She started to lean in again but Lisa took her away and went up the stairs to change into a bathing suit. I had one here from one of our previous swim dates.

A little while later I’m in the hot tub waiting for the girls to come down. Eventually I hear laughing and turn around. Lisa is in a gold bikini that perfectly shows her body, Angel wore a white bikini that seemed to be a little too small for her. Angel had pretty great tits at least a C cup. And her ass was amazing. When they joined we began to mingle and at one point Angel asked how we knew each other. Lisa looked at me and smiled.

“He is my daughter’s best friend and during one hot night he was so much more.” Angel began to look more interested. I lit my joint and began to pass it between the two women. Angel looked at Lisa again “So what was he?” Lisa smiled and started moving closer to us as she drank her wine and said “He was my lover one night and so fucking good at it.” Now I had never had someone hype me up as much as Lisa did. She did everything she could to give me confidence, and I’m forever grateful for that.

Lisa was between us and began rubbing on Angels leg and my arm. “He is really strong maybe you should give his arms a squeeze.” (Again an older woman is the best wing man) Angel moved closer and began running her hands up and down my arm and said “He is. You could probably manhandle me with these big hands.” I saw her getting turned on and began placing my hands all over her. While kissing my knuckles she began to moan softly. “Squeeze my throat. Just a little.” I had never done choking or any sort of breath play and wasn’t sure how to approach. Luckily Lisa grabbed my hand and placed it around Angels throat. “Don’t squeeze here, squeeze at this spot. She will love it. Trust me.” I did as she said and something came over Angel as soon as I grabbed her. She began to go nearly lifeless with my touch. “Harder please. Don’t stop.” Lisa moved back to the other side of the hot tub and began watching. First as a way to observe me, then I noticed she was playing with herself looking at how Angel reacted to my touch.

I whispered into Angels ear, “She’s watching you Angel. She’s touching herself looking at you.” Lisa moaned softly in the background and Angel reached down into my swim shorts and began playing with my cock. “Oh he’s so big.” Her voice broke and she looked at Lisa hungrily. Lisa ripped off her top and began squeezing her nipples.

“Can we go somewhere else please? I need him now.” Angel had asked and Lisa said, “Would you like to go to my room darling?” I started kissing on Angels sensitive neck and she barely got her “Yes please” out. Lisa was out first and began to dry off and lead us back to her room. I stayed behind both just staring at their asses. They walked up the stairs slowly teasing me with every step. We entered her room and Lisa sat in her makeup chair. “The bed is all yours. Enjoy.”

–Sexy Stuff–
Angel began kissing me more, she bit my lips softly and I played with her tits. She moaned with every pinch and I started to kiss her sensitive neck. I gave her round ass a hard smack as she moaned into me. I laid on the bed and she began taking my cock in her mouth. She sucked and licked and massaged her clit and her moans started getting louder. She asked me to get off the bed and stand up. “I think it would be hot if you looked at her while I’m blowing you. Please?” Angel had a slight innocence in her that I love. While looking up at me and I looked at Lisa who was already naked and playing with herself, Angel began blowing me again.

Lisa stood and began to walk towards us. With every step she seemed to float towards me, “She’s very good isn’t she.” Lisa watched her closely. Running her hands through her braid and down her shoulder blades. She tapped the small of her back. “Hands.” Obediently Angel put her hands behind her back and began sucking without using her hands. “She enjoys pleasing her men.” Angels gaze never left mine as she continued to suck. “Are you close?” Lisa’s words felt like soft music floating through the air. All I could do was nod. “Angel he’s close. What do you think about that?” I noticed more black tear streaks falling from her eyes and into her make up. She took me out of her mouth and began jerking me slowly. She looked up at Lisa and then at me “Will you fuck me? Please sir.”

Angel stood and got back onto the bed. She took her bottoms off and put her ass in the air for me. One of my favorite positions. I began to lick her pussy and tease her clit like I did with Lisa. Angel moaned and started rocking back into me. I spanked her ass softly and she let out a small whine. “You can go harder Sir.” I slapped harder and behind me I heard, “Angel what do you say?” I stopped licking her, Angel turned around slightly “Thank you sir may I have another?”

Another slap, another thank you. Lisa’s words felt like fire as she encouraged me. “Fuck her.” I did as she wanted and thrust my hard cock in her. Angel let out a moan and I felt her tighten up. I fucked her slow at first. She moaned and said “He feels so good” Lisa went back to her chair and began touching herself more. I fucked her more and she cried out for me. “Please sir may I cum? I want to cum so bad.” Instinctly I looked over at Lisa and she nodded yes. “Cum for me Angel you’ve been so good to me.” The words barely formed into her mouth “Thank. You. Sir. I’m. Cumming!” She let out a deep moan and began tearing into the sheets. I exploded my warm cum into her pussy and let out a groan of my own after she did. Her body finally relaxed and she caught her breathing.

“Thank you sir. Thank you thank you.” Lisa had an orgasm shortly after and began laughing and smiling. “Okay you two go clean up and I’ll go get us some water.” I helped her up and Angel went from sex crazed to her sweet demeanor in an instant. “That was fun. She was not lying when she said you were big.” In the shower I let the water beat off her body and she did something I’ll never forget. She cupped her hands around her breasts and splashed water in my face. She burst out laughing and I couldn’t even be mad. I just kissed her full lips and held her close.

Part 2 of my Lisa sex encounters ended with me finding my now current girlfriend. Angel and I became a lot closer after that night. We went out on a regular date and discovered we had a lot in common. Things were never awkward when she hung out with Airin and I. Turns out she was in Lisa’s dance class and they had been talking about me for a while. The final part of the story doesn’t involve Lisa in the picture but more or less her presence. Hope you all enjoyed.

Source: reddit.com/r/gonewildstories/comments/cmv26a/my_best_friends_mom_part_2_she_wants_to_watch_mff