A Tale of Two Families

Author’s Note: This story is a collaboration with my friend and editor, Harvey. We contributed equally to its content. We hope you enjoy it.

– – – – –

Jessica

Tim picked me up at my house for a date. His car wasn’t an SUV, it was just a sedan, but it had a spacious back seat that I hoped to use with him later in the evening. Since I expected him to be dressed nicely, I wore an even shorter black mini-skirt that showed off my sleek thighs and even higher heels that accentuated my shapely calves. I paired the little skirt with a purple button-up silk blouse that left just a little of the tops of my breasts exposed. He was wearing slacks and a dress shirt open at the collar, and when I opened my front door it was obvious from his expression that he admired my figure and loved what I’d chosen to wear for him.

“You look wonderful!” he told me, and I did a sexy little curtsy.

“Thank you, kind Sir,” I replied. “I chose this outfit especially for you, so I’m glad you like it. You’re looking pretty handsome yourself.”

He grinned. “I think your little outfit is much sexier than mine, though.”

I smiled, then tossed my long jet-black hair in a flirty gesture. I closed the door, he crooked his arm, and I slipped my hand through his elbow as we walked to his car. He opened the passenger door and I gave him a nice view all the way to my little black thong as I smiled and swung my legs around.

He drove us to an Italian restaurant, and when we were seated he took the chair next to me instead of across the table. I smiled again and rested my hand on his thigh. “Tell me more about yourself,” I invited.

A server arrived with menus and he ordered a bottle of a nice Reserve Chianti. He appeared to be unsure how to respond to my request, and fortunately for him the server returned quickly, which gave him a few moments to think while we went through the wine-service ritual. After we’d sipped and pronounced the wine quite acceptable, he turned to face me.

“I don’t know what else to say,” he began. “I told you how we wound up moving here.”

“Had you dated after your wife passed away?” I asked after sipping again from my wine glass.

“No, I wasn’t ready to get back out there for quite a while,” he said, and then took a sip of his wine. “Have you dated much since your divorce?”

“No.” I hesitated, and then collected my thoughts. “Frankly, I wasn’t able to find a man I could really relate to, and since we moved here you’re the first man I’ve dated.”

“Well, I have to say I consider myself extremely lucky you’re available, because I’m very interested in you.”

We were interrupted by the server returning to take our dinner orders. I ordered chicken scallopini and Tim selected the veal parmigiana.

When the server had left, I said, “I’m interested too, Josh is a great son, but I’ve missed having an intimate relationship with a man near my age.”

“I’ve been in a similar situation with Angela,” he said carefully. “She’s tried really hard to step into her mother’s role and take care of me.”

“I don’t want you to upset you, but may I ask you something?”

A little nervous expression broke over his face. “You can ask me anything, but I won’t promise you an answer,” he teased.

“”Has she taken over all the aspects of your late wife’s role?”

His face turned into a red ember of embarrassment and he couldn’t look me in the eye, and I gave him a look that told him I’d guessed something he hadn’t intended to reveal.

“Your secret’s safe with me, and I understand completely how something like that can happen.”

“How can you possibly understand that?” Suddenly it was my turn to blush and I looked down and ran the tip of my finger along my wine glass. “You understand because you’re having sex with your son, aren’t you?”

My body froze for several seconds, then our eyes met. “Yes, I am,” I said solemnly. “Are you disappointed or upset?”

“No… I… ummm… I think it’s hot,” he admitted.

My eyes widened. “You’re really not put off by it?”

He grinned. “That would be a little hypocritical, right?”

“Yes, it would,” I said shyly.

“This is a heavy topic for a first real date, isn’t it?”

“It is, it’s very difficult for me to talk about this, I’ve never… you know… done anything like this until recently.”

“May I be honest with you?”

“Yes, please,” I whispered.

“I like you, I want to pursue this with you, but we need to be open and honest with each other, don’t we?”

“Yes, we do.” I thought for a moment. “Can we agree not to be judgmental? I like you too, but I need to feel comfortable if we’re going to talk about this.”

“I agree; no judgment, no criticism, from either of us, okay?”

I smiled. “Okay.” If he wanted us to talk about this very awkward subject, I thought he should begin. “How did it start with you and your daughter?”

He took a deep breath. “My wife and I were very… ummm… experimental… and she kept a very detailed diary that Angela read while she was sorting through my wife’s things. She actually initiated things with me and changed our relationship.”

I smiled. “You enjoy being with her, don’t you?”

“I do,” he acknowledged. “It’s almost like, I’m not sure how to say this, but at times it feels like I have my wife back. It may not be healthy, but that’s how it feels.”

“I can understand that.”

He took a sip of his wine. “What’s it like with you and Josh?”

I took a deep breath and a big drink of my wine. He’d been so honest and forthcoming that I didn’t want to hold back, and I told him the truth. “I’m not sure how to say this either, but he’s more forceful, or… ummm… demanding… with me. Much more so than my ex-husband or any of my other lovers.”

His eyes widened. “Demanding?”

“He has a young man’s exuberance, and he seems to like being more in charge, it’s something that I’ve honestly never experienced to that extent.”

He smiled. “But you like it, don’t you?”

“I’m still trying to get used to it; but yes, I like it,” I said shyly.

“Will you tell me more about it?”

“This is very difficult for me, but I’ll try.”

“What do you mean when you say he takes charge? You know I want you, and I want to know what pleases you.”

“I’m flattered that you want me, and I want you too.” I hesitated, then said slowly, “I’m discovering that I have a submissive streak, and I sometimes like things to be a little rough. So I like it when he takes control of me, both physically and verbally, and commands me to do things for him.”

“That’s very erotic.”

“It’s like he’s opening up a new world for me, one that I never even knew existed,” I said impishly. I was beginning to feel the heat and desire build within me as we spoke and I opened up to him.

“Would you want me to be like he is?”

“No, I want you to be yourself and I don’t want you to change what you like for me.” I thought for a moment. “Just know it’s something I like and something I’m willing to try with you, if you want.”

Our dinners arrived, which briefly put our conversation on hold. As we began to eat our delicious entrées, he brought up another somewhat awkward topic. “You told me he likes to take control of you, he’s more… ummm… aggressive with you. I don’t have to worry about my daughter’s safety, do I?”

“No, not at all. First and foremost, I’ve raised my son to be a gentleman, and he is,” I said reassuringly.

“Okay, good. She’s a strong woman and she can take care of herself, but I had to ask.”

“They had a connection when they went out, didn’t they?”

He smiled. “She was quite smitten with him, he made a very good impression on her.”

“Josh felt the same way.” I thought for a couple of seconds, then asked, “How do you feel about that? Your daughter, who’s now your lover, getting close to another man?”

“I’m okay with it. Despite everything we… ummm… do together, I want her to also be with a young man who’s her age.”

I smiled. “So, no jealousy, no resentment?”

“None.”

“Good, I feel the same way. I really hope Josh and Angela continue to hit it off, because it sounds like they would really be good for each other.”

“Speaking of two people enjoying each other, I really enjoyed our time together, everything we did. However, you did leave me wanting,” he said.

“That won’t be the case this evening, I promise,” I said seductively.

His lips split into a big smile. “Okay.”

– – – – –

We finished our dinners, Tim settled the check, and we left the restaurant. I didn’t want to be concerned about Josh being home, so I suggested we go to a hotel and Tim readily agreed. He drove us to Green Valley Ranch and he got us a room. As we stepped inside, I took a moment to look around. The walls were painted an off-brown that complemented the dark-brown carpeting. There was a king-size bed in the middle of the room and an ocean mosaic painting above the headboard.

I walked slowly towards the bed, then turned around to face him. His eyes ran up and down my body, drinking me in, and I began to unbutton my blouse, revealing a very sexy little silk bra that barely contained my large breasts.

“You have such a beautiful body,” he said seductively.

I let my blouse drop to the floor and slid out of my little skirt. “It’s all for you,” I whispered. He took a step forward and we exchanged a hot, passionate kiss, and I began unbuttoning his shirt. He reached down and unfastened the front clasp of my bra. It swung away from my body and my breasts swayed before him. My nipples were erect and I was almost certain he could smell my arousal. I reached down and rubbed his cock through his pants and then hurriedly unbuckled his belt, unclasped the latch on his trousers, and worked his trousers down his legs. I slid his boxers down and his big erect cock slapped against his stomach. I took him in my hand and began to gently stroke him. “God, it’s beautiful,” I murmured.

“I’m glad you like it,” he said in a low, deep tone.

“Here’s how desirable I think you are,” I whispered. I got onto my knees in front of him and wrapped my lips around the head of his cock. He had a large, mushroom-shaped head, and I loved the way his pre-cum tasted.

“God, that feels so good,” he grunted from above me.

I slowly worked him deeper, ensuring my mouth stayed warm and wet. I spent about a minute working him in and out and then relaxed the muscles in my throat and took him all the way down to the root. I hummed around his shaft, and the vibrations caused him to moan. I was sure he could see me smile when I felt that, and I pulled back long enough to say, “Let it go whenever you’re ready; I really want to taste you.”

“It won’t be long,” he said. “You’re about to get all you can take.”

I reached up and took his sack into my hand and gave the large orbs a gentle squeeze. “Give it to me, baby,” I cooed. “I want to taste you so bad.”

I went down on him again, taking him deep into my throat. His body stiffened, his breathing changed, and his cock twitched. I backed away so I held only the head, then rubbed his chest to signal I was ready. That was all he needed. Thick jets exploded into my warm mouth as I gently sucked on the head. I swallowed frantically to keep up with the volume, and after several seconds the bursts subsided and I swallowed one last time.

When he’d finally spent his release I sat up, licked my lips sexily, and gave the head of his cock a playful kiss. “I loved doing that for you,” I said sweetly.

“It was amazing,” he gushed, “but now it’s your turn.”

He helped me to my feet, put both of his palms on my breasts, and kissed me hard with exuberant passion. When I opened my mouth he slid his tongue in aggressively. I instantly melted, and our tongues urgently danced together. We kissed with white-hot passion and then he lifted his mouth from mine, bent down, and took a nipple into his mouth. I moaned in pleasure and put my hands on his head and ran them through his thick hair to hold him close as he sucked on my hard little nub. He took my other breast in his hand, feeling its firm weight, and rubbed his thumb over its stiff tip.

“Mmmm,” I whispered. “That feels sooo good.”

Suddenly Tim was in a hurry to move ahead and he playfully pushed me onto the bed. I opened my legs wide, revealing my tiny wet lace thong. He roughly peeled it off of me and slid two fingers into my very sodden pussy.

“Oh, yes,” I groaned emphatically.

His fingers were deep inside me and he curled them upwards and began to gently rub, putting pressure on my G-spot. Then he lowered his head and licked up and down my slit, collecting some of the moisture. I squealed when his tongue glided over my clit, and he continued licking and slurping up my juices while continuing to rub the tips of his fingers deep inside me. When he locked his lips around my clit and lashed it with his tongue, my body began to climb.

“Yes… fuck… yes… I’m almost there… don’t stop…” I moaned.

My body violently shook and convulsed as a powerful orgasm overwhelmed me. He held his fingers deep inside me but withdrew his tongue from my clit. Just as I started to come down from my mind-blowing high, he made delicious little circles on my clit with the tip of his tongue and pushed me into another, even bigger release. I clamped my thighs around his head and shivered and shook and screamed in pleasure and he withdrew his fingers from inside me and wrapped his arms around my thighs so his mouth remained in contact with my vagina. I was moving so violently the bed was rocking, and Tim stopped what he’d been doing and just held me as I struggled to catch my breath and recover.

“God, Tim, that was fantastic,” I said through deep gasps of breath. “You really know how to pleasure a woman.”

“You inspire me,” he replied. “You’re just so beautiful, so desirable.”

“Thank you,” I said with what I hoped was obvious sincerity. “I’m really glad you feel that way about me.” I paused, then added, “It was just amazing, you’re amazing.”

He slid up my body and we shared a long, passionate kiss and he held me tight in his arms. While we shared our passionate embrace, he slid his thigh between my legs and our bodies sensually tangled together. I loved feeling his hard, toned chest against my breasts and his tight, firm legs against mine. It had been so long, years, since anyone had stirred this type of passion within me and I desperately yearned for this to be more than sex, more than one night of coupling. I wanted this to be the start of something, something real. He was an amazing lover, but he was still a guy, and I didn’t want to push him too hard, too quickly.

Our eyes romantically met. “Whatcha thinking about?” I whispered.

“You, honey.”

“Good thoughts, I hope.”

He paused for a moment. It was almost as if he was trying to find the right words. “I’ve… I thought I’d never feel this way again, about any woman, after my wife died.”

I wanted to be honest with him without making any demands. “We’ll take it slow, okay. I know we’re moving fast… but… this was something we both wanted, right?”

“I wanted you from the moment I saw you,” he admitted.

I smiled and we exchanged a little kiss. “Things are just… you know… a little complicated with our kids, huh?”

“They are, but I want this… I want you… I love my daughter and everything I do with her, but I’m not letting you get away from me,” he said sensually.

“I enjoy everything I have with Josh, but I’m not going anywhere, I promise you that, okay?”

He smiled. “Okay.”

I felt his returning erection pressing against my thigh. It’s time. “I want to feel you inside me,” I whispered.

He slid away from me and I got onto my back; I opened my legs and he crawled between them. He took his cock in his hand at the base and ran the tip up and down the lips of my vagina, opening them, and then he eased himself inside me. As he continued to push forward, I felt his big cock slowly opening and simultaneously filling me until our bodies rested together and knew he was fully inside me.

“God, you feel so good,” I purred.

He eased back out until the head nearly came out of me and then pushed forward again, and the motion nearly took my breath away. “Your pussy feels so good, so tight,” he murmured.

He was taking his time, savoring every second as our bodies gently collided together and then separated. His sweat was sensually dripping onto me and mixing with mine. He leaned in and we shared a long, hot kiss. “Put your weight on me, hold me down, push me into the bed,” I moaned.

Our bodies crushed together. I wrapped my thighs around his torso and moved underneath him, meeting his gentle thrusts. “Just a little faster now, baby, let me feel every inch of you.”

He gradually picked up the pace and the angle was perfect. His thick shaft was caressing my clit, pushing me closer to release, and I wanted to bring him with me. “Come inside me when you’re ready, honey.” I squeezed the muscles in my vagina, milking him, and he stiffened up and his breathing changed. Just as I felt him squirt deep into the walls of my pussy, my orgasm washed over me and my world momentarily went dark.

When my senses were back about me, I found that he’d collapsed on top of me and we held each tight. His eyes opened and we exchanged a long sensual kiss. “We’re going to be doing a whole lot more of that,” he said with a little grin splitting his lips.

“I’m yours, whenever you want me.”

– – – – –

After we recovered and caught our breath we showered together and scrubbed each other clean. Once we had dried each other off, we slipped back into bed and snuggled together under the covers. A serious look broke across his face and I knew he must be thinking about something important. After a few seconds, he hit me with it. “I have a request.”

“A request? And just what would that be?” I said playfully.

I could tell that he thought it was too late to turn back, he was committed, and he just blurted out, “We’ve been together, and I loved it, but I want to watch you with Josh.”

My jaw dropped in surprise. “Why?”

“You told me he can be rough, even… ummm… aggressive… with you. And you… you know… you like that, right?”

A deep blush broke over my face and I honestly didn’t know how to proceed. I’d always enjoyed rough sex, with my husband and with a couple of other lovers before we’d married. But it had actually been my son who’d truly dominated and taken control of me. “He can be very aggressive at times,” I shyly admitted.

“My wife and I were very adventurous and we loved to play with others, but I’ll be honest with you; I’ve never attempted to take control of a woman or do anything like what you’ve described.”

“It’s something that you’re interested in, then?”

“Yes.” He thought for a moment. “I never imagined I could learn anything from someone so young, but maybe I can. I want to see how he treats you, what you like, how rough you like things to be. I want both of us to really enjoy the sex we’re going to share.”

This felt like such a huge, momentous step. Not only having sex with my son, but letting someone else, especially someone who I was quickly developing feelings for, watch me with him. I also had no idea what Josh would think about any of this. “I’d need to talk to him, okay?” I paused for a moment to collect my thoughts. “But if you want this, then I want it too.”

“Just let me know what he says, okay?”

We shared another slow, lingering kiss. “I will.”

– – – – –

Josh and I sat down the next morning. After I cooked him breakfast, he quickly turned our conversation to my evening with Tim.

“So how did your date go?” he started. “You look happy this morning.”

“It went very well, we had a nice talk and I learned some more about him and his daughter.”

“Tell me what happened.”

I decided to play somewhat coy. “We had a really nice dinner, and he was very open and I learned much more about him and his daughter.”

“I heard you get in at 5:00 this morning, so I think your date involved a little more than dinner and conversation,” he teased.

A little blush broke over my face. “We ended up getting a hotel room,” I admitted.

He moved his hand to my thigh and gently rubbed it. “You’re going to give me details,” he said somewhat more sternly.

A little shiver coursed through my body as I felt his not-so-subtle control over me. “What kind of details are you looking for?” I asked shyly.

He tightened his grip on my thigh. “You’re going to tell me everything.”

“I went down on him.”

“And you swallowed his nut, didn’t you?”

I looked down, unable to meet his intense gaze. “Yes,” I whispered.

“What then?”

“He gave me oral sex.”

His hand slid upward and he ran the tips of his fingers over the front of my thong under my little jean skirt. “He got you off, didn’t he?”

“Yes,” I murmured as I replayed the torrid events of last evening in my mind.

Josh easily found my clit through my thong and gently rubbed, sending little tingles through my core. “He loved how your hot, wet pussy tasted, didn’t he?” he said gruffly.

“Yes.”

I let out a deep, low moan as he slid my thong to the side and his finger entered me. “You’re wet just thinking about him, aren’t you?”

It was getting difficult for me to concentrate on our conversation. “Yes, I’m wet, Josh.”

“I can guess what happened next, but I won’t, you’re going to tell me,” he said demandingly.

“We made love, gently and romantically.” I willed my mind to focus and take back at least a little control of the situation. “Is that enough detail for you?”

“Did you like it?” he said somewhat more snidely. “It sounds a little boring to me.”

I cut my eyes at him. I was okay, more than okay, with him taking control of me like this, but I didn’t care for his tone. “I had a wonderful evening with him and he’s a good man.”

He slid a second finger inside me and his thumb gently manipulated my clit, and I let out a low, deep moan. “So, this deep conversation with your new lover, tell me about it.”

I took a deep breath and tried to get my breathing under control amidst his smooth ministrations. “He’s having sex with his daughter.”

His mouth dropped open in shock and he withdrew his hand. “He’s screwing Angela?”

I inwardly smiled. She didn’t tell you everything, did she? “Yes, he is.”

He stared at me in silence for several seconds as his mind attempted to wrap itself around this new information. “I’m… ummm… I’m not sure what to say.”

“I know this is upsetting,” I said soothingly, “but we have the same relationship, don’t we?”

“Yes… but… it’s just a lot to take in,” he admitted.

In many ways my son was wise way beyond his years, but now just a little immaturity was showing through and I quickly got back into my motherly role. “He’s taking liberties with her that I’ve let you take with me.”

Slowly, he seemed to be coming around. “Yes… I guess he is.”

“They’re both very special, I can tell what an exceptional young woman she is from the way he talked about her. I don’t want to see you mess this up with her, okay?

“I like her, Mom. I really like her, and I won’t mess it up.”

“Good, honey. And you’re okay with me seeing Tim?”

He smiled. “Yes, I am. It’s nice to see you happy with a man again.”

“I love this too, honey, and I’m glad you’ve started a relationship with a girl your own age.” I paused, then reassured him, “Tim knows about us, honey, I’ve shared everything with him and he’s okay with our relationship. In fact… he’s curious about… some of what we do together.”

Josh looked puzzled. “What do you mean?”

“You’re very controlling with me, baby, very demanding at times, and he’s curious about that. I confessed to him that I like when you take control and are rough with me.”

“You told him everything, huh?”

“That’s what lovers do when they’re serious about each other and trying to build something real.”

He smiled. “Okay.”

“There’s more if you’d like to hear it.”

“Sure, tell me.”

“He’s very curious about our relationship, the control that I give you, how you treat me, and he’d like to witness it first-hand.”

His eyes widened. “Like… ummm… watching us?”

“Yes, baby; what would you think of that?”

“I… ummm… I don’t know.”

I didn’t want to press him too hard. I knew this was a lot for him to take in. “Would it be weird to you, him watching us?”

It took him several seconds to respond. “I’ve never done anything like that before.”

“I know you haven’t, honey.”

“I wouldn’t change anything I do with you,” he said sternly. “I know you like him, but he’d have to be willing to watch everything, everything I like doing with you.”

“All you have to do is be yourself,” I said sweetly. “Will you try this for me?”

“Okay, he can watch us.”

“Thank you, honey.”

“Will Angela know about this? I don’t know what she’d think of any of this.”

“I’m not sure, honey, but I could talk to him about it.”

He thought for a moment and I could see the wheels in his mind spinning. “I haven’t had sex with her yet, but I think it’s going to happen.” He paused. “If I let him watch us, I’m going to want the same thing at some point, I’d want to watch him with Angela,” he said somewhat harshly.

My eyes widened, and I knew my son well enough to know that it was unlikely he was going to budge on this. “Why?”

“Fair’s fair, right? And I’d like to see how she is with him, to see how he treats her, much like he wants to see me with you. She and I made out a little, but we haven’t had sex yet. Besides, even if we had, I’d want to know more about what she likes.”

This is gonna be either very good or very bad, I thought. “I’ll talk to Tim and see what he says. When should we do all this, assuming he agrees?”

“This Saturday evening,” Josh instructed.

Even though he was my son, I loved it when he took control and ordered me around. “Okay, baby, I will.”

His hand moved again between my legs and he ran his finger over the front of my wet thong. “Go upstairs, get naked on our bed, and wait for me,” he commanded. He leaned in and gave me a slow, hot, passionate kiss.

“Yes, Sir. Should I put my heels on?”

“Only if you want to be allowed to come,” he replied with an evil grin.

– – – – –

To be continued…