“Noah, are you ready to go?” Samantha asked. “Abigail’s giving us a dirty look and I’d rather get moving.”
I nodded. “Yeah, just let me get my bag.”
I fetched my backpack out of my locker and then slammed it shut. I looked down the hallway where Abigail was watching us. She was half-hidden behind the corner and was staring at the pair of us intently. I gave her a wave and a smile. Her face flickered slightly, and then she slinked back out of sight.
“I don’t know what you see in her. She’s a creep.” Samantha complained. “Even the guys think so.”
“I wonder what other guys think of you?” I asked, smirking slightly.
“Ah! That… um… probably that I’m an uncool loser nerd.” She laughed awkwardly.
“I don’t know…” I smirked moving closer to her. “I see a beautiful, sexy hotty and my best friend.”
Her face turned red. “N-Noah…”
There was a slam on a locker, and we both turned to see Abigail glaring again like a disapproving chaperone. This relationship where I was dating both of them wasn’t as free-spirited as the relationship I had with my sisters and mother. Abigail and Samantha didn’t exactly get along. They both tolerated each other, but it wasn’t like they were friends. Mackenzie might secretly have a cuckold fetish, but that didn’t mean these girls enjoyed the idea of me being with other women.
The pair had ended up agreeing, some kind of pact between them. They had me on alternating days, no exceptions. If I wasn’t available that day or they had plans, it was too bad. The other also couldn’t take advantage of those days. Also, there was no touching or romantic gestures at school. No kissing, sex, or hugs. Naturally, if I was seen kissing or hugging both women, it wouldn’t just hurt my reputation, but it’d hurt theirs as well. I was willing to agree with such conditions.
I wasn’t sure how long this peace treaty would last, but for the moment, it was good enough for me. I wondered what would happen if I tried to bring Anna into it. I hadn’t spoken to her recently. I needed to call her too. The problem was that I didn’t know what to do if I did.
I had used her as a ride several times. I had teased her with sex and then got her to do things for me, even forcing her to break the rules and risk getting in trouble for me. Then, after all of that, I had ghosted her. She hadn’t sent me any texts, but neither had I. Well, since the situation was reversed, maybe she was ghosting me? Either way, would it be the responsible thing to give her the sex she desired, or break it off with her completely? I genuinely didn’t know. It wasn’t easy taking responsibility.
Tonight, however, I had other responsibilities. I had set up another study date with Samantha. After catching us together in Samantha’s room, her parents didn’t’ seem to blame me at all. Rather, they quite liked me. In the case of her mother Jennifer, her desires were obvious. She wanted me to come over so she could unload her desires on me.
It was for that reason that I wanted to go to Samantha’s house. In line with my desire to shape up, that also pushed me into wanting to end the toxic relationships in my life, and other than the teacher I was blackmailing, it was my relationship with Samantha’s mother that felt the most self-destructive. Before being my girlfriend, Samantha was a friend, and I did care about her, so I knew that this kind of stuff had to end.
I had already discussed things with my mom. No, I didn’t tell her I was sleeping with Jennifer. I didn’t know how she’d react if she learned I was sleeping with someone else’s mom too. When the girls got jealous and when they didn’t mind was a confusing land mine that I still didn’t fully comprehend. Mom knew where I was going and had given me permission. I was going to leave with Samantha. We were going to be picked up by her dad, we’d go to her house, and then we’d study. If her mom put the moves on me, then I’d break it off just like I did with my teacher.
That was the plan, but when the car pulled up and I glanced in it, I was dismayed to see that it wasn’t her dad that was picking us up, but her mom. Her mom also had a wide grin on her face as soon as she looked at me. If Samantha was paying attention, it would have been really obvious to see the relationship we had, or maybe it was just my own nervousness telling me that.
As soon as I saw Jennifer, I started to get in the back of the car with Samantha, only to regrettably hear her speak up. “You know the rules. You can’t sit together. Only proper distance between you two. Noah, why don’t you sit up here?”
“Mom! You’re right there. There is nothing we can do!” Samantha whined. “And why are you picking us up anyway?”
“That’s your dad’s rules. He’s busy right now. He’s having a spa day.”
“A spa day? When does dad take a spa day?”
“When I buy him one.” Mom snorts, but then she shoots me a wink where her daughter couldn’t see.
I couldn’t help but swallow hard as I moved to the front seat, sitting down next to Jennifer. Samantha’s dad was the one safety factor in all of this. For my teacher, we were in school and she naturally couldn’t make a scene. For Jennifer, it was her husband being nearby. Yet, she had apparently accounted for that. She had sent her husband away by giving him a spa day, just so that she could have some alone time with me. My plan was already hitting some hiccups. I just had to remain firm and end things as painlessly as possible. Yet, I could feel Jennifer checking me out, and I didn’t dare look back to see if Samantha was even noticing.
“I have an idea.” Jennifer suddenly announced. “How about I take you two out for ice cream before we go back to the house.”
“Huh? Why?” Samantha asked from behind me.
“You’re going to be studying, right? You’ll need sugar to keep your energy up.” She smiled at me.
Did every smile seem like a flirt, or was it just me? I decided to play clueless for now. At the very least, if Samantha saw it as this one-sided thing, it’d only be her mother to blame.
“Sure, I can use some ice cream.” I used the opportunity to look back at Samantha, only to see she was using her phone and wasn’t looking at her mother at all.
“Yeah, sure, whatever.” She responded without looking up.
My friendly look grew sour, and as I turned back away, I got a peek at her mom’s predatory look. Have some damn awareness, Samantha! It’s the kind of behavior that would turn someone into a cuck. She already was sharing me with several others, so she was already there. I cleared my throat and stiffened a bit, but it wasn’t like I could do anything to flag her down or warn her. Thus, I could only wait as we drove off from the school and headed to wherever she was going to drive us. I didn’t understand what her plan was. Was she trying to bribe me with ice cream? Did she think that sugar was an aphrodisiac? I definitely couldn’t follow her thought process.
We pulled into an ice cream stand, and I was a bit surprised to see that the line was out the door. It wasn’t even that hot out, being early spring, but it was really busy.
“What will you have?” Jennifer asked.
“Just vanilla,” I responded.
She nodded, pulling money out of her wallet, and then turning back and shoving it in front of Samantha. “I’ll have a fried ice cream, and he’ll have a vanilla.”
“Hey, what? I’m supposed to get it?”
“Heh, aren’t you the dutiful girlfriend? You won’t even get your boyfriend an ice cream? Did I raise such a lazy daughter?”
Samantha glanced at her mom, and then me. I didn’t have an expression on my face that I was aware of, but my eyes held a bit of pleading that she would understand the situation. However, Samantha remained dense, giving a sigh, and then opening the door and walking out. Her mom hadn’t even parked close to the line. It was literally on the other side of the stand. The area we were in was sort of hidden and private.
“Oh…” I let the word out loud as I realized what was happening.
“A vanilla boy…” Jennifer leaned toward me, and it was only then that I noticed she wasn’t wearing a bra. “You’re so innocent. I’m going to have to teach you all kinds of new… flavors.”
I couldn’t help but look away, not sure if I wanted to cry or laugh. “I’m not that innocent.”
“We’ll see…” She reached out and grabbed my dick through my pants, immediately going for the zipper.
I grabbed her wrists, which felt somewhat familiar with what I had to do with my teacher only a short time before.
“What are you doing?” I tried to use logic first. “There are people everywhere. Your daughter will be back any minute!”
“Hehe… that line takes at least fifteen minutes to get through, and I also ordered fried ice cream. They have to make that special and it will take almost ten minutes. The way I see it, we have almost a half-hour before she gets back.”
“S-seriously?”
She had gone that far just to get some dick? She even had this place scoped out and had the timing right just so she could play grab-ass with her daughter’s boyfriend?
“Oh, don’t worry. This is just the hors d’oeuvres. I’m just going to get you warmed up. When we get to my house, that’s when the real fun begins. My husband is away, and I got enough chores and errands to keep Samantha busy while I entertain you. Heh, I can’t wait to see your cumming face as she cluelessly goes about her chores.”
“Do you want to do that to your daughter?” I asked incredulously.
“Samantha needs to learn that men are just a bunch of sluts. I’m teaching her a good lesson. I’m older and probably won’t get this chance again. Samantha will have plenty of time to find another… or if she sticks with you, I wonder how long we can keep this going. Fondling the groom on his wedding night sounds fun!” As she said this, she went to kiss me, but I turned my head away.
“No!”
She stopped for a second, pulling back slightly. “No?”
“I’ve been thinking about this lately, and I think we should break it off. I care about Samantha, and I don’t want to hurt her. I think it’s just better for both of us if we had a clean break!” I declared with my eyes closed, not managing to be any more elegant than my previous time.
I waited for a moment and hearing nothing, I opened my eyes to see Jennifer still staring at me. However, she didn’t look stunned like my teacher did. Instead, she looked amused.
“No, I think not.” She responded after a moment.
“What?”
“As long as you keep seeing my daughter, you’re going to have to keep fucking me.” She responded, reaching out and tapping my nose playfully. “If you don’t, I’ll just tell her, and your relationship will be ruined.”
I shook my head in confusion. “I could tell your husband just as easily. If either of us tells…”
“I believe that’s what they call a mutually assured destruction.” Jennifer giggled. “Now that I’ve had a taste of you, I’m not giving it up. Come on now, don’t be so surprised. I asked around about you with some of Samantha’s peers. You have a reputation in school for being a complete pussy slut. I know Samantha isn’t your only girlfriend, and I know you still want to fuck me.”
She grabbed the neck of her blouse and pulled it down, causing her large tits to pop out the top. “So, let’s stop wasting time, and get hard for mommy!”
“Noah, are you ready to go?” Samantha asked. “Abigail’s giving us a dirty look and I’d rather get moving.”
I nodded. “Yeah, just let me get my bag.”
I fetched my backpack out of my locker and then slammed it shut. I looked down the hallway where Abigail was watching us. She was half-hidden behind the corner and was staring at the pair of us intently. I gave her a wave and a smile. Her face flickered slightly, and then she slinked back out of sight.
“I don’t know what you see in her. She’s a creep.” Samantha complained. “Even the guys think so.”
“I wonder what other guys think of you?” I asked, smirking slightly.
“Ah! That… um… probably that I’m an uncool loser nerd.” She laughed awkwardly.
“I don’t know…” I smirked moving closer to her. “I see a beautiful, sexy hotty and my best friend.”
Her face turned red. “N-Noah…”
There was a slam on a locker, and we both turned to see Abigail glaring again like a disapproving chaperone. This relationship where I was dating both of them wasn’t as free-spirited as the relationship I had with my sisters and mother. Abigail and Samantha didn’t exactly get along. They both tolerated each other, but it wasn’t like they were friends. Mackenzie might secretly have a cuckold fetish, but that didn’t mean these girls enjoyed the idea of me being with other women.
The pair had ended up agreeing, some kind of pact between them. They had me on alternating days, no exceptions. If I wasn’t available that day or they had plans, it was too bad. The other also couldn’t take advantage of those days. Also, there was no touching or romantic gestures at school. No kissing, sex, or hugs. Naturally, if I was seen kissing or hugging both women, it wouldn’t just hurt my reputation, but it’d hurt theirs as well. I was willing to agree with such conditions.
I wasn’t sure how long this peace treaty would last, but for the moment, it was good enough for me. I wondered what would happen if I tried to bring Anna into it. I hadn’t spoken to her recently. I needed to call her too. The problem was that I didn’t know what to do if I did.
I had used her as a ride several times. I had teased her with sex and then got her to do things for me, even forcing her to break the rules and risk getting in trouble for me. Then, after all of that, I had ghosted her. She hadn’t sent me any texts, but neither had I. Well, since the situation was reversed, maybe she was ghosting me? Either way, would it be the responsible thing to give her the sex she desired, or break it off with her completely? I genuinely didn’t know. It wasn’t easy taking responsibility.
Tonight, however, I had other responsibilities. I had set up another study date with Samantha. After catching us together in Samantha’s room, her parents didn’t’ seem to blame me at all. Rather, they quite liked me. In the case of her mother Jennifer, her desires were obvious. She wanted me to come over so she could unload her desires on me.
It was for that reason that I wanted to go to Samantha’s house. In line with my desire to shape up, that also pushed me into wanting to end the toxic relationships in my life, and other than the teacher I was blackmailing, it was my relationship with Samantha’s mother that felt the most self-destructive. Before being my girlfriend, Samantha was a friend, and I did care about her, so I knew that this kind of stuff had to end.
I had already discussed things with my mom. No, I didn’t tell her I was sleeping with Jennifer. I didn’t know how she’d react if she learned I was sleeping with someone else’s mom too. When the girls got jealous and when they didn’t mind was a confusing land mine that I still didn’t fully comprehend. Mom knew where I was going and had given me permission. I was going to leave with Samantha. We were going to be picked up by her dad, we’d go to her house, and then we’d study. If her mom put the moves on me, then I’d break it off just like I did with my teacher.
That was the plan, but when the car pulled up and I glanced in it, I was dismayed to see that it wasn’t her dad that was picking us up, but her mom. Her mom also had a wide grin on her face as soon as she looked at me. If Samantha was paying attention, it would have been really obvious to see the relationship we had, or maybe it was just my own nervousness telling me that.
As soon as I saw Jennifer, I started to get in the back of the car with Samantha, only to regrettably hear her speak up. “You know the rules. You can’t sit together. Only proper distance between you two. Noah, why don’t you sit up here?”
“Mom! You’re right there. There is nothing we can do!” Samantha whined. “And why are you picking us up anyway?”
“That’s your dad’s rules. He’s busy right now. He’s having a spa day.”
“A spa day? When does dad take a spa day?”
“When I buy him one.” Mom snorts, but then she shoots me a wink where her daughter couldn’t see.
I couldn’t help but swallow hard as I moved to the front seat, sitting down next to Jennifer. Samantha’s dad was the one safety factor in all of this. For my teacher, we were in school and she naturally couldn’t make a scene. For Jennifer, it was her husband being nearby. Yet, she had apparently accounted for that. She had sent her husband away by giving him a spa day, just so that she could have some alone time with me. My plan was already hitting some hiccups. I just had to remain firm and end things as painlessly as possible. Yet, I could feel Jennifer checking me out, and I didn’t dare look back to see if Samantha was even noticing.
“I have an idea.” Jennifer suddenly announced. “How about I take you two out for ice cream before we go back to the house.”
“Huh? Why?” Samantha asked from behind me.
“You’re going to be studying, right? You’ll need sugar to keep your energy up.” She smiled at me.
Did every smile seem like a flirt, or was it just me? I decided to play clueless for now. At the very least, if Samantha saw it as this one-sided thing, it’d only be her mother to blame.
“Sure, I can use some ice cream.” I used the opportunity to look back at Samantha, only to see she was using her phone and wasn’t looking at her mother at all.
“Yeah, sure, whatever.” She responded without looking up.
My friendly look grew sour, and as I turned back away, I got a peek at her mom’s predatory look. Have some damn awareness, Samantha! It’s the kind of behavior that would turn someone into a cuck. She already was sharing me with several others, so she was already there. I cleared my throat and stiffened a bit, but it wasn’t like I could do anything to flag her down or warn her. Thus, I could only wait as we drove off from the school and headed to wherever she was going to drive us. I didn’t understand what her plan was. Was she trying to bribe me with ice cream? Did she think that sugar was an aphrodisiac? I definitely couldn’t follow her thought process.
We pulled into an ice cream stand, and I was a bit surprised to see that the line was out the door. It wasn’t even that hot out, being early spring, but it was really busy.
“What will you have?” Jennifer asked.
“Just vanilla,” I responded.
She nodded, pulling money out of her wallet, and then turning back and shoving it in front of Samantha. “I’ll have a fried ice cream, and he’ll have a vanilla.”
“Hey, what? I’m supposed to get it?”
“Heh, aren’t you the dutiful girlfriend? You won’t even get your boyfriend an ice cream? Did I raise such a lazy daughter?”
Samantha glanced at her mom, and then me. I didn’t have an expression on my face that I was aware of, but my eyes held a bit of pleading that she would understand the situation. However, Samantha remained dense, giving a sigh, and then opening the door and walking out. Her mom hadn’t even parked close to the line. It was literally on the other side of the stand. The area we were in was sort of hidden and private.
“Oh…” I let the word out loud as I realized what was happening.
“A vanilla boy…” Jennifer leaned toward me, and it was only then that I noticed she wasn’t wearing a bra. “You’re so innocent. I’m going to have to teach you all kinds of new… flavors.”
I couldn’t help but look away, not sure if I wanted to cry or laugh. “I’m not that innocent.”
“We’ll see…” She reached out and grabbed my dick through my pants, immediately going for the zipper.
I grabbed her wrists, which felt somewhat familiar with what I had to do with my teacher only a short time before.
“What are you doing?” I tried to use logic first. “There are people everywhere. Your daughter will be back any minute!”
“Hehe… that line takes at least fifteen minutes to get through, and I also ordered fried ice cream. They have to make that special and it will take almost ten minutes. The way I see it, we have almost a half-hour before she gets back.”
“S-seriously?”
She had gone that far just to get some dick? She even had this place scoped out and had the timing right just so she could play grab-ass with her daughter’s boyfriend?
“Oh, don’t worry. This is just the hors d’oeuvres. I’m just going to get you warmed up. When we get to my house, that’s when the real fun begins. My husband is away, and I got enough chores and errands to keep Samantha busy while I entertain you. Heh, I can’t wait to see your cumming face as she cluelessly goes about her chores.”
“Do you want to do that to your daughter?” I asked incredulously.
“Samantha needs to learn that men are just a bunch of sluts. I’m teaching her a good lesson. I’m older and probably won’t get this chance again. Samantha will have plenty of time to find another… or if she sticks with you, I wonder how long we can keep this going. Fondling the groom on his wedding night sounds fun!” As she said this, she went to kiss me, but I turned my head away.
“No!”
She stopped for a second, pulling back slightly. “No?”
“I’ve been thinking about this lately, and I think we should break it off. I care about Samantha, and I don’t want to hurt her. I think it’s just better for both of us if we had a clean break!” I declared with my eyes closed, not managing to be any more elegant than my previous time.
I waited for a moment and hearing nothing, I opened my eyes to see Jennifer still staring at me. However, she didn’t look stunned like my teacher did. Instead, she looked amused.
“No, I think not.” She responded after a moment.
“What?”
“As long as you keep seeing my daughter, you’re going to have to keep fucking me.” She responded, reaching out and tapping my nose playfully. “If you don’t, I’ll just tell her, and your relationship will be ruined.”
I shook my head in confusion. “I could tell your husband just as easily. If either of us tells…”
“I believe that’s what they call a mutually assured destruction.” Jennifer giggled. “Now that I’ve had a taste of you, I’m not giving it up. Come on now, don’t be so surprised. I asked around about you with some of Samantha’s peers. You have a reputation in school for being a complete pussy slut. I know Samantha isn’t your only girlfriend, and I know you still want to fuck me.”
She grabbed the neck of her blouse and pulled it down, causing her large tits to pop out the top. “So, let’s stop wasting time, and get hard for mommy!”
