As you’ll recall from my last entry, my college age son, Todd (the name I’ll use for him, not his real name) and I had become a bit more comfortable with each other when he was home on Christmas break. It was very tame, yet very fun (you may want to read it first, it’s a short one). Since then, we have repeated that session a few more times when he was home for long weekends, not going beyond what we’d done before. We take our time and made it last a little longer with me pleasuring myself also. We would talk about things and share some experiences while we pleasured ourselves, and I even confessed some light details about the massage parlor I worked at when I was in college. He was shocked by that at first but it seemed to turn him on as well.
What he found more surprising was when I told him that my best friend Sharon, whom he’s known all his life and thought of like an aunt, also worked there and managed the place. He in turn opened up about some of his experiences and experimentations in high school and his first year in college. I was learning that he was more similar to me than I had imagined. We both enjoyed the honesty as well as the pleasure of these sessions and it really opened up our communication bond with regards to everything else in life. Since he came home from college in late May, we had only managed one session. Having a summer job and spending time with his old friends kept him busy, but it was mainly his younger sister’s presence in the house that kept him out and about. She was quite the home body and the two of them often did not get along very well. Being four years apart they did not have much in common. None the less it was nice having him home, especially since he was very helpful; and we both got a kick out of exchanging a knowing glance or wink in conversation, here and there.
For over twenty years my friend Sharon and I were very close and got together several times a year. However, around two years ago when I left my husband, I moved to a town a little further west, which now put Sharon and I about two hours apart. The distance and traffic now made the trip less easy and convenient as it had been; we’d gone almost two years without a visit. Earlier this month everything finally aligned well for a get together with July 4th being a long weekend. My daughter was spending the weekend at her father’s place, so when Sharon texted me about visiting I told her I was totally free and she could stay over if she liked.
When that Saturday afternoon finally arrived I was anxiously awaiting her arrival, having not seen her for a while I had really missed her. Finally, her car pulled into the driveway around two o’clock and I watched her get out and walk to the front door. She looked as sexy as ever. Sharon was now 62 years old, but did not look it. She could easily pass for late forties, fifty at the most. For those who don’t recall from past stories, Sharon is about five feet seven inches tall and curvy, maybe around one-eighty if I had to guess. She still has her great figure with long legs and a full round butt, however her best feature has always been her enormous boobs. Her hair still naturally chestnut brown with a few grey streaks and, with her smooth face, she appeared as pretty and sophisticated as women half her age.
When I opened the door we both squealed with excitement to see one another, hugging and lamenting the amount of time that had passed since our last meeting. As we loosened our embrace and held each other’s wrists, I couldn’t help but take a look at her chest in the tight white V-neck top. “My goodness Sharon,” I said with a smile. “Ah yes Dee,” she responded, “I know you’ve missed them.” We both laughed out loud. I quickly gave her a peck on the cheek and asked softly, “Do you mind?” She calmly replied, “Not at all dear,” and smiled. With that I pulled up her shirt and lifted her bra and went right to work, sucking her nipples while I held her large soft globes in my hands. She moaned her approval. After maybe a minute I lifted my head and said, “Ok that’ll get me by until later,” as we both giggled again.
Just then, and quite unexpectedly, my son Todd walked into the room from the kitchen. “Oh my goodness,” he sighed with a smile, looking at me still holding Sharon’s boobs with her shirt up. “Ok, ok, nothing to see here,” I laughed as I pulled her shirt and bra back down. He then said hello to Sharon, and her to him. She remarked that he’d grown up quite a bit since the last time she saw him. “Yes,” I said, “He’s even got a year of college behind him already.” She asked if he was 18 and he replied, “Yes and I’ll be 19 very soon.” Sharon chuckled and reminded me that was the first thing I’d said to her when we met long ago at the spa. After a little more small talk, he told us he was heading to his friend’s place and said goodbye.
After he left we spent some time sitting in the kitchen, talking and catching up, as well as some kissing mixed in. We managed to keep ourselves under control since we had plans on going out on the town. We both freshened up and changed into our going-out clothes. Sharon was wearing a black skirt and heels, with a silky purple sleeveless top, and I was wearing my favorite red cocktail dress with high platform sandals. For two older women, me 43 and her 62, I think we were looking damn good.
After a short scenic drive, I took us to a great seafood restaurant that has a nice outdoor cocktail cabana bar. We hung out for a few hours after we finished eating. The conversation was great as we talked a lot more about the old days at the spa, with all the sexy details, more so than we typically had when we hung out in the past. It occurred to me and I mentioned that this was actually the first time that she and I had ever hung out when we were both single. She said that the same had occurred to her earlier on the drive. At this time, it was getting later and a DJ was setting up as a younger crowd was meandering in. On the heels of the idea of both of us being single I leaned in and asked her if we wanted to try to score a couple young guys and get laid. She grinned and thought for a moment then said, “Actually I’d prefer just having fun with you.” I probably blushed and smiled, telling her that was quite the perfect answer. We paid our tab and headed back to my house.
When we walked in, I was surprised to see my son in the living room playing a video game. It wasn’t too late so we both sat down on the sectional sofa and watched a bit while we continued our random topics of conversation. He was fairly quiet, just playing and listening to us chatter. The nostalgic conversation took some risqué turns but, overall, we kept it fairly tame with lots of laughs. After about a half hour, while still playing his game, he chimed in and said to Sharon, “Mom tells me that you used to manage the massage parlor that she worked at while she was in college.” Sharon’s eyes widened a bit. I quickly interjected, “Its ok he pretty much knows everything, well not everything, but I’ve told him about the spa.” Sharon smiled and said that it was cool that we were open with each other. I abruptly laughed and stated, “You have no idea.” I responded by saying that he shares our healthy perspective towards sex and that we didn’t have any secrets.
He then turned the game off and set the controller down, turning to Sharon and casually stated, “Yeah and we masturbate together now and then too when my sister isn’t around.” I thought Sharon was going to fall off the sofa for a second. She looked at me and grinned as I was sure I was blushing again. I said, “Yes but we don’t touch each other, we just discuss things from our sex lives and relieve our tension over the conversation.” Sharon nodded, “Well that is very, very nice indeed.” She looked at me and said, “I guess I’m not at all surprised knowing you as I have.” She looked at him and said, “Your Mother has never been shy or repressed regarding sex as long as I’ve known her.” “Oh I know,” he replied, “She’s always had that vibe about her according to my friends.” I blushed again. He continued, “Yeah she’s been the favorite mom in the neighborhood since junior high and I’ve gotten used to hearing my buddies talk about what they’d like to do with her.” I chimed in, “All fantasies I assure you.” I wasn’t even aware until he told me that last Christmas. Sharon chuckled. “Yeah,” he said, “And if they only knew I get to see her naked whenever I want they’d be so jealous,” and he laughed as well. Sharon sat back and nodded again, “I am actually very impressed that you guys have such open communication and a healthy attitude toward such things. Again, I shouldn’t be surprised.” She continued, “I knew your Mother when she was your age and you remind me a lot of her now.”
As we continued with the finer details about our little masturbatory sessions, Sharon asked Todd if she could ask him some questions since her curiosity was peaking. He replied, “Sure why not,” looking at me. I nodded, “Certainly, you can tell her anything that you tell me.” She started by asking him if he was sexually active to which he said yes, but on and off, depending on whom he was dating at the time. She responded saying that she beats the off-times must be rough for a guy his age. He agreed. She said that she heard that from many college guys years ago who patronized the spa. He smiled and said, “Oh yeah that’s right, I’ll bet that was good for business for you.” She smiled saying, “You catch on quickly.”
He turned the tables and asked her few questions about the spa, more detailed than he’s asked me before. “So, you gave guys hand-jobs,” he asked. She smiled and said, “Yes, mostly.” He asked if we worked in the nude. Again, she answered, most of the time. Cool, he nodded, “All different types of guys?” “Yes,” she said, “A large variety, and believe it or not, a woman here and there as well.” Again, he nodded, and said. “Wow.” I think he was genuinely curious because, as far as I know, there aren’t any health spas in our area, or many left even around the cities. Since the internet came about, this was likely something he’d never heard of before I had told him about them.
Sharon jumped back in asking if any of his girlfriends had given him a good hand-job. He answered no but, to Sharon’s surprise, he said that his one guy friend has given him some good ones. Sharon then asked if he had given his friend any in return. “Oh yeah,” he said, “We started that back in high school.” This was not a surprise to me since he had told me about this a few months earlier; he had experimented lightly with a couple guy- friends over the years. Sharon asked him if he enjoyed it and he said that it was good side-fun, but that he was far more turned on by women overall. She glanced over at me and said, “Well this apple didn’t fall far from the tree at all did it?” I pursed my lips jokingly and said. “Whatever.” Todd laughed and said, “Oh its cool, I know Mom is a lesbian.” I piped up and said, “Bisexual young man, bisexual,” laughing all the while. “Oh ok,” he said, “but you’re like pretty fifty-fifty I think.” Again I said, “Whatever,” with a smirk. Sharon was now cracking up laughing. By this time, he was sitting right next to her as she was interviewing him. I was leaning back around the corner of the sectional maybe eight feet away just taking it in, semi amused, semi turned on. Sharon continued, so when did you start masturbating? He answered, around ninth grade and that his school friend introduced him to it along with some DVDs. She asked him how often he did it back then and he told her every day, sometimes a few times a day. Sharon then asked him what he used to get aroused back then. He replied that sometimes it was videos, or just his imagination about girls from school, and that sometimes he’d peek at me when he had the chance. I half sat up and said, “What?” As this was new information to me!
“Are you serious Todd,” I asked, half startled yet half amused. Sharon sat back thoroughly entertained. Truthfully this entire Q&A scene was extremely fun, especially with her doing the questioning. “And when did this happen.” I asked him, because I really had no idea. “Oh pretty often,” he answered. “Such as,” I pressed on. He grinned and said, “Well initially I used to peek on you when you were changing or after you showered. Then there was the time when you thought I was at my friend’s house, but I came home and you were sunbathing topless on the deck. I was up at window beating off the whole time.” “Oh my goodness,” I exclaimed. Again both he and Sharon were laughing. And then he said, (oh boy I was thinking) “I peeked on you and Dad doing it a few times when you thought we were asleep.” “Well,” I responded, “I’m glad I helped you through the high school years.” “Oh and,” he continued, “remember last Thanksgiving when I was home, that guy from the car dealership came over.” Yes, I replied. “Well, I was hiding around the steps by the den while you gave him that blowjob before he left.” “Oh my God Todd,” I said surprisingly somewhat embarrassed. “Oh really,” Sharon interjected, “is that really so bad?” “No,” I laughed, “it’s not, and I guess I have no room to judge.” “Certainly not,” Sharon giggled. She then turned to him and asked, “So you liked watching her and seeing her nude?” “Oh yeah,” he said, “why not.” He continued, “When I first hit puberty I really didn’t notice because, ya know, she’s my Mom. But after hearing all the things my buddies were always saying, I did start to notice that she was pretty hot.” “Awww that’s sweet,” I said, sitting back and blushing. “So,” Sharon continued, “the next month after the car guy, you were home for the holidays and this is when you guys first masturbated together?” I answered, “Well that time just he did and I watched.” “Yeah,” he said, “she just took her top off and showed me her boobs.” “Oh,” Sharon said, “and how exactly did that come about?” Todd answered, “I had wanted to ask her for a while if she’d let me see them close up. So, when she came home from that party I was checking them out hoping she’d notice.” “Oh I noticed,” I chuckled. “Yeah,” he said, “and I didn’t even have to ask, she offered to show them to me.” I laughed, “Yes but you did say you were missing your girlfriend and were gonna have to jerk off later, so I was just trying to help.”
Sharon was smiling and asked, “Did you finish in front of her?” “Yeah,” he said, “in like a few minutes.” “Yes,” I added, “turns out he is really into big boobs, another thing he and I have in common.” “Really,” Sharon replied, “it does sound that way doesn’t it?” We all laughed loudly. Sharon then asked him if he liked seeing her boobs earlier in the day, to which he answered, hell yes. “Would you like to see them again,” she asked. He nodded and she slipped her top over her head and undid her bra, releasing her huge breasts for him to look at. I grinned as I had an idea where she was going with all this. “Would you like to feel them,” she then asked. Without saying anything he began squeezing them and lightly rubbing her nipples. As I’ve mentioned, Sharon’s boobs are very large and very full with big round nipples; seeing him enjoying them was very erotic. At that moment, she glanced over his shoulder at me and smiled. I returned a naughty grin back to her.
Sharon then asked him if she could show him how we did things back at the spa and give him his first good hand-job from a woman. He could barely manage to speak, but stumbled, “Umm yes, yes, I think.” He quickly turned and looked at me as if for approval. I giggle and said, “Hey don’t let me stop you guys.” Sharon asked me if I had any massage oil, to which I quickly hopped up and retrieved some, as well as a sheet, from my bedroom. Sharon spread the sheet on the floor and told him to remove his clothes and lie down on his stomach.
Going through the typical routine she disrobed to her panties and then massaged his back and thighs for a bit to get him relaxed. About ten minutes in, she asked him to turn over which he did. She then poured oil on her own chest as well as his and, from above, began rubbing her boobs up and down his mid-section to his very erect penis. This was getting me hot, so I slipped my cocktail dress off, and was now sitting back in the sofa, topless in my panties with my legs half spread, watching the show. After taking her sweet time, Sharon finally took hold of his cock, causing him to moan a bit as it twitched. She began to slowly stroke it and a good bit of precum ran out of the tip. Sharon quickly bobbed her head and expertly collected it with her tongue, barely touching his penis. By now I was drenched. I pulled my panties to the side and started rubbing and fingering myself.
As she was stroking him firmly and slowly, she held it straight up and made eye contact with me and nodded her approval of his size. I smirked and nodded back. As I rubbed with one hand, I tugged my nipples with the other hand. Sharon smiled at me again. After about twenty minutes of her masterfully getting him close to the edge and backing him down five or six times, she leaned up and asked him how her hand-job compared to his friends. “Oh my god, are you kidding,” he panted, “this is unbelievable.” “That’s good,” she replied. “Are you ready to cum for me now,” she asked him. “Oh gawd yes,” he declared. With that, she lowered her head and took just the head of his penis in his mouth. She sucked it firmly for a few seconds, then lifted her head off it and began pumping just the upper half of his cock rapidly. In no time, massive bursts of semen were flying straight up in the air, landing everywhere: on himself, on Sharon’s boobs, and on the sofa next to them. I had never seen him cum anywhere near this much before; so clearly, he was really turned on. As he’d almost finished shaking, they both looked over at me just in time to see me nearly slide off the couch having my own intense orgasm. We all recovered and cleaned up the area. Then we were back to laughing and teasing one another again. One thing was clear though, we all enjoyed that tremendously. Sharon gave Todd a soft kiss and patted him on the ass and told him to go up and shower and get to bed, which he did, clearly exhausted. As she and I walked to the bathroom to clean up, she said, “It’s my turn now you know.” “Oh you better believe it is,” I replied. After quick showers, Sharon and I went to bed and made love for another hour and a half before calling it a night.
The next morning we all comfortably slept in a bit. Over breakfast the three of us had a few laughs over the evenings events. Sharon again confirmed with Todd that she gave the best hand-job he ever had. Again, he fell over himself declaring how amazing it was, and said the only thing that would be better would be better would be to actually fuck her. She paused for a moment and looked at me. I glared back and said, “Hey masturbating with him is as far as I go or need to see.” “But,” I continued, “I need to run to the store for some things, so what you guys do while I’m gone is up to you.” I returned a few hours later and Todd was gone. Sharon had let me know that they did have sex and that it was very good, but didn’t go into more detail than that. I was very happy they had fun, as did I the night before. Sharon left for home later that afternoon. When Todd got home, we joked a bit about what happened with Sharon that morning. Our talk turned into some discussion about the times he’s watched me in the past; this led to us having one of our quick but intense sessions together in the early evening before his sister came back later that night.
So, Sharon’s overnight visit was extremely enjoyable for everyone. After all was said and done, everything was back to normal, at least by our definition.