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17
25M update 3 on Mother’s Day plans
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Guiltypleasures5280 is age 25
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I know Mother’s Day is today but we celebrated yesterday just because of my work schedule. And it went so well…. Sorry for the length of this in advance.

TLDR: I spent the day with my mom swimming in her pool, tanning, i cooker her dinner, after dinner I gave her the massage and she returned the favor. She then mentioned how she missed what we use to do and mentioned doing it again for old time sake. We started to masturbate on the couch together. She asked if she could feel it and I let her. Which let to her stoking me. Eventually I was playing with her clit while she did. Then the moved to straddling me and grinding on my cock.

So between the last update I had texted my mon a bit and I took her joking about me swimming naked as a open door to joke around a bit. I texted her and told her maybe I’d chose a Speedo to swim in. She sort of took the bait and said she doubted I even owned one (she was right but I didn’t tell her that). I responded with telling her I’d only wear one if she wore a bikini instead of a one piece. She didn’t respond for a while but when she did she just jokingly said. She won’t wear a bikini because she hasn’t owned one for years because she outgrew all her tops years ago and jokingly said she doubted I’d even fit in a Speedo. I just laughed and agreed that we won’t wear anything special. That was the last we talked before I headed over.

I went over around 1:30 and just wore my compression shorts, a yellow and black pair of swim trunks and a t shirt. I packed my slim khaki pants and a nice black t-shirt to change into after. On my drive over I was in my head a bit and was a bit too excited so when I got there I was semi hard. So I sat in her driveway for a few minutes to calm myself down. Once i got that down I got out and grabbed all the groceries for dinner and my change of clothes and headed to the door. It was open so I busted walked in. My mom was nowhere to be found so I just started putting the groceries in the fridge. After a few minutes she came downstairs from her room. She didn’t realize I was there apparently and when she got downstairs she was wearing an absolutely stunning navy blue one piece suit that had openings cut out just below her breasts and the back was more or less completely open. It definitely showcased a fairly significant amount of underboob. The bottom hugged tightly around the middle of her butt and overall it showed off just the right amount of her body. She saw me in the kitchen and apologized for not being covered up and I said it was no problem I had my swim stuff on too. She came over and gave me a huge hug. She pressed herself tightly into me and I could feel her breasts squishing into my abdomen area. Her thigh was sort of between my legs and definitely pressing against my crotch. I finished putting stuff away and asked her if she had any sunscreen. She told me it was upstairs in the hall closet and asked me to grab her some of the lower strength one up there as well. So I went upstairs and grabbed it. When I got back down she she was just sitting on the couch on her phone. I sat next to her and asked if she’d mind putting some on my back. Of course as any mom would she obliged. I took my shirt off and turned to the side and she squirted out the sunscreen. When her hands pressed down on my back they were warm, I felt her fingers open up a little as she began to spread the lotion across my back and shoulders. She then offered to get my arms so she put some more down and began to massage down my arms. It was kinda already getting me a bit hit and bothered. I loved seeing her smaller hands trying to wrap around my biceps. Once she was done she asked me to get her back since it was not covered by her suit. So she turned to the side and I put some lotion on my hands and smeared it over the open area on her back before I started to massage it in. My hands must have been a little cold because as a soon as my hands touched her I could feel her tighten up a bit and goosebumps shot across her body. As I rubbed the lotion in. I could feel her relaxing into it and she was breathing a bit harder. That only made my situation worse. I started to get a little semi hard but it was still well contained in my compression shorts so I wasn’t worried about it. Once I finished up I took the bottle and began to apply it to my chest and I saw her just kinda watching me. After a little she began to do the same. Her suit left her chest exposed a fairly decent amount on top. And watching her press her fingers into her soft cleavage was hard to avoid watching. Once we were all lathered up we headed out to the pool. I jumped right in and she sat at the edge leaving her feet in. We just talked for a bit before she slid in and we just talked. We hung out in the water for a little before we got out and laid in the chairs in the sun for a bit. She gout out before me and sat down. When I got out I just got out on the side and I felt my suit cling to my legs and I reached down to adjust myself and caught her eyeing me a bit. I asked her if she wanted a drink. She asked me to grab her one of her white claws and that there was some beer in there for me. So I went inside and grabbed the drinks and came back out to sit next to her. We sat and enjoyed our drinks in the sun for a few hours. Nothing really happened worth noting other than passing glances from both of us. Around 4 we decided to head inside and clean up. Her spare bedroom is used as a closet so she offered me to rinse off in her bathroom. So I headed upstairs and turned the shower on. Grabbed a towel and hopped in. While I was in there I heard the bedroom door open and she said she was just grabbing something for downstairs. I saw her reflection in the mirror look towards me out of the corner of her eye. But I kinda shyly kept my back mostly to her. She was in and out fairly quick. When I got out and dried off I went to out my clothes on. After I was dressed I was looking for my swim suit but it was gone so I figured that’s what she grabbed.

I headed downstairs and she was wrapped in a towel and the washing machine was running. She said she hoped I had a nice little rinse off and that she was going to do the same. But I was definitely a bit distracted with her literally only wearing a towel. It sat just maybe inches above her nipples and just above mid thigh where it stopped. I kinda stuttered in my response and asked if she needed anything done while she rinsed off. She said there was nothing so I said I’d start getting dinner ready. She went upstairs and was up for probably around 30 minutes getting rinsed off and ready. I could only help but think about what she could possibly wear while I was prepping everything and getting the sauce cooking.

I heard the stairs creek a bit as she came down and I literally froze when I saw her. She had this absolutely beautiful black sundress on. It clung tight to her body and didn’t hide any curves. It was deep cut and left almost nothing to the imagination. It stopped a little above mid thigh. And she definitely didn’t have a bra on because the only thing on her shoulders were the skinny little straps holding up her dress. She looked absolutely beautiful. Her hair was curled up and thick. She had makeup on and these short little heels on.

Eventually I snapped out of it and told her she looked great. She thanked me and asked if I needed help. I said no and she was welcome to hang out with me or just relax and dinner would be ready in about 30 minutes. She pulled up a chair to her island in the kitchen and crossed her legs over each other and just watched me cook. I couldn’t help but take a glance at her whenever I could. And she definitely noticed but she didn’t mind and reciprocated the passing looks. Once dinner was ready I took her and sat her down at the table. I dished up the food and brought it over to the table. I grabbed a bottle of wine and poured us each a fairly heavy glass. And we sat down and ate. There wasn’t a ton of talking but about half way through dinner she paused and looked at me and genuinely thanked me for the day and spending my time with her making her dinner and taking care of her. I blushed a bit and said it was well deserved and I was happy to do it. We finished dinner up and I cleaned up and let her relax some more. We sat down on the couch and had a few more glasses of wine to finish off the bottle. When I went to grab the other bottle I came back with the bottle of lotion she requested and asked her if she still wanted the massage.

She said if I still wanted to it would be really nice. So I asked her if she wanted to change because I couldn’t really put lotion on her back with that dress on. And she said just go grab a towel from upstairs and she’ll just drop her top down and lay down. I didn’t hesitate for a second. I went upstairs and when I came back down she had pulled the top of her dress down and was laying face down on the couch. Her breasts were squished under her and bulging out at the side of her body. I offered her the towel and she said to just turn around and she’d lay down on it. So I handed it to her and she did her thing. When she was done I turned back around and she had just repositioned herself on top of the towel. She was laying on the couch so I half knelt next to her and put some lotion on her upper back. I began to massage it in and I could hear her breaths with each squeeze and press. I worked down her back to just above her hips when she adjusted herself a bit and pulled down her dress a little more exposing the rest of her lower back and a little bit of the top of her ass. So I put some more lotion down and rubbed that in. This all took maybe 15-20 minutes. I asked her if her legs were still sore to which she responded with they were. So I offered to massage there too. And a bit to my surprise she asked me to turn away again. And when I turned back she had pulled down the dress and it was laying on the floor. She had the towel under her and a part of it up covering her back side. So I moved down towards her feet and put some lotion on her legs/ my hands. I worked the lotion in. Massaging her tight feet and slowly working my way up the back side of her legs. Her legs were loose and relaxed. But the closer to got to her ass. Her legs tightened up a bit and her breathing was getting a little faster and deeper. I eventually got up just below the crease of her butt and I hand lightly slipped up towards her curvy hips/ ass. She let out a sigh as I did and I just didn’t stop. She seemed to be okay/ enjoying it. So I rubbed the outside of her hips and lower part of her butt for a minute before I asked if she wanted me to move the towel. At this point I was starting to get turned on and the bulge in my pants was growing a bit. She had her head turned facing me but with me kneeling at her side I don’t think she could see anything.

She didn’t respond right away so I kept rubbing down her hips and the back of her legs. Eventually she said she thinks that would be nice as long as I didn’t mind. So I pulled back the towel and exposed her whole back side. And that’s when I lost what little self control I had left. I got the rest of the way hard and tried to keep it tucked down my pant leg the best I could. I squirted out a decent bit of lotion on her and began to kneed it in. Her breathing quickly started to pick up and I could tell she was probably enjoying it as much as I was. I spent about 5 minutes there before she asked me to put some more in the front of her legs. I said of course. She didn’t ask me to turn around this time. She just took the towel and flipped around managing to (unfortunately keep her breasts and crotch mostly covered. I put some more lotion on her and began to work again from her feet up to her thighs. But as I got closer to her thighs they were really tense until she completely relaxed. I was about half up her tight when she relaxed and she didn’t stop me until I was just inches away from the crease in her hips. She was basically panting at this point. Ash she moved to adjust herself I swear I could hear a slight sound of wetness but I wasn’t sure. I asked her if she was sore anywhere else and she said no that she felt amazing after that. I was still rock hard so I stayed kneeling but she took the towel and sat up. Wrapping it the rest of the way around her body as she did and offered me to sit down on the couch. My hands were covered in lotion so I told her I’d need to wash my hands first. I got up and turned my back slightly to her and attempted to adjust my crotch as I did. I want to the kitchen and washed the lotion off and went back to sit next to her. Still in her towel she just rested her head in my shoulder and thanked me again. But she also asked me if I was sore at all. I told her I was only sore really in my chest and legs. And she offered to give me a quick massage. She asked me to take my shirt off and lay on my back. So I pulled the shirt off and laid down. Resting my arms in an attempt to hide my erection. She tucked the towel into itself to keep it up and she moved to the position I was before kneeling next to the couch. She put lotion on my chest and began to massage it in. Her hands were soft and gentle. She focused on my chest for a few minutes before asking how I wanted to go about my legs. And at this point she definitely had noticed the bulge in my pants. She didn’t focus on it but asked me if I wanted to grab another towel to cover myself up. I didn’t really bother trying to hide my crotch. I got up and went to grab another towel. When I came back she said it was okay and to lower my pants and cover myself up. So she turned her back to me and I dropped my pants. And covered up the best I could. I pointed my cock up towards my head because that’s really the only way to have it not so obvious. I laid back down and she turned around. She pumped lotion on my legs and began massaging. She spent another few minutes on my thighs and joked that I was making her hands tired. So I told I felt better and she could stop. When she did. I wasn’t sure if it was intentional but she pushed herself up off the couch to stand and brushed the back of her hand across my lap. She went and rinsed her hands off and came back. I had wrapped the towel around my waist and tucked it in and was sitting up. She came and sat next to me. She rested her head against my arm again and we just sat and relaxed for a minute. I was still pretty evidently hard and she’d occasionally glance at it. I broke the silence after maybe 2 or 3 minutes. And brought up how she said she missed our time together when I still lived at home. She moved her head and didn’t respond right away and I got nervous. But she eventually said that she did and really enjoyed how close we use to be. I swear I could see my heartbeat in my crotch as she said this. I didn’t really know how to respond so I just agreed. We sat for a bit more before she said she wished I lived at home still and that she’s been really lonely since I moved out. I just told her I only live a few miles away and would happily come keep her company any time.

We just talked about life and everything for a few minutes and even though we were both sitting in towels practically naked on the couch my erection began to dissipate. She profusely thanked me for dinner and her massage. I told her again she absolutely deserved it and I’d be happy to do it again. She adjusted and still with her towel on. Pulled one leg up on the couch and got a bit more comfortable. But the way she moved her leg onto the couch. If I wasn’t sitting right next to her. It’d be a clear shoot looking at her crotch.

She looked like she wanted to say something but hesitated a few times before she finally spoke up. I could hear the nervousness in her voice and she spoke extremely softly. She asked if I would want to re-live old times. I didn’t really get a chance to respond before my brain was doing it’s own thing and I began to get hard again. But the way to towel had moved over a few minutes I wasn’t really contained all that well and the towel began to tent and rise up. She just giggled and said “I take that as a yes?” I just laughed a little and said. I don’t see any harm in that.

I moved my hand over the towel and slowly started to stroke myself to fully hard. And watching her face as I got hard and she watched was all I needed to get going. She soon followed lowering her hand down to her crotch. I could hear her wetness as she toyed with herself. Eventually my towel worked it’s way down and started to expose the tip of my penis. And her eyes really didn’t look away at all until I moved the towel out of the way and she audibly laughed and said it was bigger than she remembered.

The comfort we had before was starting to come back and she removed her towel exposing her whole body. She definitely showed some slight signs of how she’s aged. But mostly I noticed she had put on a little weight and her breasts were definitely bigger and slightly saggier. And just as I remember she was still hairless. I could feel a little precum drip down my shaft making it a little slicker as I stroked. After maybe a minute or two she stopped and looked back at me and just stared for a moment before she again spoke up with a shakey voice. Once she finally was able to say it. She asked me if it was so wrong of her to ask me to feel it.

I didn’t really know how to respond and I just moved my hands and nodded my head to her. She reached her hands out and just sort of cradled it from the underside. She didn’t do anything at first but hold it. Almost like she was just feeling the weight of it maybe. But it felt so good to feel her soft hands even just holding it. After a few seconds of that her hands started to move slightly and she asked me if it was okay as she started to lightly stroke me. He hands could only wrap part way around me as she did. Slowly she progressed from the little short strokes to moving her hands up and down the entire shaft. Other than my precum there was nothing to lubricate it so she took a small pump of the lotion and began to spread it around. I could feel that I was rock hard and she was completely focused on stroking it. I didn’t even really think about it. But I leaned over and kissed her. It wasn’t until our lips met that I worried if she’d freak out for some reason. But she returned it with a soft passionate kiss. I adjusted and scooted closer to her and put my hand on her lower back. And my other resting on her thigh. This continued for a few minutes before she exhausted towards me and moved her thighs apart. I moved my hand from her thigh down towards her clit. And I slowly began rubbing his her clit. Not fingering her. Again we did this for a bit before she moved again to her knees on the couch and moved in of her legs to the other side of me sort of half straddling me. She bent over and kissed the tip of my penis a few times before she lowered her hips down. My cock was pinned between us and right in the slit of her vagina. She began to grind up and down my shaft firmly pressing herself down. I could feel each time it pressed hard on her clit her body would tremble a little. I was oozing my precum all over on my abdomen as she did this. We continued to kiss as she was grinding on me. Her heavy but soft breasts pressed firmly against my body and I could feel her nipples hard against my skin. As this continued we shared a few muffled mumbles and moans between each other. After maybe 5 or 6 minutes of just the grinding alone I could feel her body shake and her breathing rapidly increased with the speed of her moving her hips. She mumbled out an “oh fuck” before she let out a deep sigh followed by her moans muffled as she buried her face into the crease of my neck. She rode out her orgasm before asking if I was close. She looked at the pool of precum on my and seemed surprised by the amount. My cock was completely covered in her wetness and she reached down and began to quickly stroke my cock squeezing it firmly. After maybe a minute more I warned her I was about to cum. She sped up even more and said it was okay to cum for her. And that was all I could take. Just those words alone I felt myself begin to tighten up. I tried to hold it back as long as I could but only a few seconds later I lost that battle. At first a small dribble of cum came out the tip. Followed by several long thick ropes of cum that managed to shoot up and hit me in the chest with the first shot. And the rest more or less straight up and all over her lap and a little bit on her chest. I don’t know how else to describe it but she looked at me in a loving caring way as she continued to stroke me as I finished my orgasm. I was out of breath and my head tipped back a bit and the silence fell over us. We just sat there for a moment with her straddling my legs and my cock slowly becoming soft in her hands. I reached down and handed her the towel I had previously been wearing to clean up the mess. She wiped herself off and I cleaned myself off. And we just sat for a while. I guess taking in what we just did. Oddly enough what broke the silence was her laughing a little bit and saying how she couldn’t believe what we just did and how bad it was. She wasn’t saying in a way of regret at all but more disbelieving what we did. I laughed a little with her and said jokingly “so I guess we don’t ever tell anyone about this” and she just pushed my chest and said “what do you think?” Still laughing a bit. It was around 9 maybe at this point and she said she needed to get cleaned up and I was more than welcome to wait for her before I headed home. So she went upstairs and showered off before coming down again wearing just her panties and a t-shirt. She walked me to the door and shy and quietly thanked me for an amazing early Mother’s Day. Before giving me another soft passionate kiss as I was opening the door to head home.

Sorry this was so long. There’s a lot of details I left out because of that. But if you want to know more please let me know and I’ll try to fill in wherever you need!

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