Chapter 3

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.