Lucky Over 40 Ch. 03: Her Lead

This is the third part of the story of two single 40somethings that met on-line and started an adventurous sexual relationship. It's basically about exploring completely heterosexual kinks, and contains things like female dominance, CFNM with some reluctant exhibitionism, mild humiliation, anal play, cum play -- including eating some of his own cum, and face sitting. Among other things, there is NONE of the following: pain, bondage, incest, underage sex, homosexuality, bisexuality, or nonconsensual sex, of any kind. If anything above bothers you, don't be upset if you decide to keep reading! (Please DO make use of story Tags to see what you may like, or not.)

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I really felt I was a lucky guy right now. I met this sexy, sensual woman on-line and we hit it off. When we finely got into bed, we hit it out of the park. The sex was great, and she was as worked up about it as I was. Today would be my fifth date with Jill, and the deal was that she got to take the lead, since I had led the action on our last date, and I had pushed her a little out of her comfort zones. She admitted that she liked it all, but she intended some pay back when she was "in charge," as she put it. As with the last date, I was pretty aroused all day thinking about tonight. The difference was, then I got aroused planning our date, and now I was the one wondering what she was planning, especially given her comments about not forgetting how I had pushed her last time.

We planned that she would pick me up at my house tonight, and when I got home from work I saw her car already in the driveway. I walked in and called out "Hello," wondering where she was, how long she had been there, and what she was up to, but there was no response. When I walked into the living room I saw her sitting on the couch, dressed in a loosely open white silk, sleeveless blouse and a nice short, loose black skirt. Her legs were casually crossed and she was nonchalantly swinging her foot, which was wearing a fairly steep wedge sandal. The lack of response to my calling out already had me a bit apprehensive, but those sandals really got my attention.

I'm a bit over six feet tall, and Jill is right up there as well, fully able to look me in the eye without cocking her head. On our first date she told me she was glad to finally go out with a guy she didn't look down at, but those sandals would certainly change things, by at least a couple inches. I thought this would be an interesting evening.

"Hi there. I didn't expect you quite so soon," I said. "You look very nice."

"Thanks. I wanted to surprise you; it's just a taste of more to come this evening. And you're overdressed right now, Rob. You need to take off those clothes and get ready to hop in the shower for me." I agreed and started to go to my bedroom, but she stopped me, "No, right here. Go ahead and strip, then we'll head to the bathroom."

"OK, are you joining me for a shower? That would be nice," I said as I took off my shirt and kicked off my shoes. I liked the way this seemed to be heading.

"No, I'm already prepped, but you aren't," she replied somewhat mysteriously. I guessed she was playing a similar game that I had done with getting her ready for our last date, but doing it a little more intensely. I dropped my pants and started to pull down my briefs when she said, "Turn around first." I raised my eyebrows a bit in surprise, but complied, bending over to take my underwear all the way off. "I like that view. Very nice," she commented. "Let's go."

I headed for the bathroom and she followed at a little distance, saying, "Yes, I like that ass." When we entered the bathroom she said, "Where's the trimmer you use for your beard? Give it to me. I told you I wanted to trim up your bush a bit, since you like the way mine's trimmed." I handed her a cordless trimmer, that was fortunately, or not, fully charged. I was a bit apprehensive, but also getting aroused. My cock was swelling a bit, but not yet quiet erect.

"Stand in the shower," she told me, "so we don't get hair all over the floor. I did, and she knelt on the bathmat next to the tub. She turned on the trimmer and said, "Not quite as short of your closely trimmed beard, I think," as she began to crop the hair above my cock. Lifting my cock, she moved on down to my balls, then told me to turn around, open my legs and bend over. She continued across the back of my scrotum and my perineum making sure it all was neatly trimmed.

Then she told me to pull my ass cheeks apart and she put the vibrating trimmer in my crack, shaving around my anus. The feeling was quite erotic and I was getting aroused. Her free hand slid across my balls and along my stiffening cock. "You seem to like this, don't you? Too bad I'm done now. OK, turn on the water and clean yourself up. Be sure all that loose hair is gone, babe," and she set down the trimmer and walked out, but called back over her shoulder, "And no jerking off in the shower, Rob."

I took a quick shower, but made sure I got all the loose hair washed away since I didn't want any left to cause itching or get in the wrong place during the evening's festivities. Very shortly after I shut off the water, Jill came back in, her long blond hair now pulled back in a ponytail, and said, "Before you dry off I want to be sure you cleaned everywhere. Hand me the soap, please, babe." She began to lather up my cock and balls, which of course, got them to react. "You like this, too, don't you? Turn to your right and bend way over for me," which I did, putting my hands on the wall for support.

She continued to rub around my balls and cock from behind, then she slid a hand into my ass crack, stroking up and down in it. "Bend over a little more, and open those legs as much as you can, bend your knees." As I did, she rubbed my asshole and then pushed a finger inside. I tensed up reflexively, and her other hand grabbed my cock from the front. "Just relax, babe. You enjoy this, too, don't you?"

I didn't think she expected an answer, but she squeezed my cock and pushed the finger in me as far as she could, asking again "Don't you, babe?" I just sort of grunted in affirmation, and she said, "I know you do. We'll make sure you're nice and clean inside and out." She stroked her finger in and out of my ass, rotating it around, slowly stroking my cock lightly at the same time, but not jerking me off. After nearly a minute, she abruptly let go, pulled her finger out of me, and said. "Rinse off and dry yourself, then come back to the living room." She rinsed her hands in the sink, dried them, and left.

When I was done, as quickly as I could, I wrapped the towel around my waist and went into the living room, to find her sitting at the end of the couch again. "You're overdressed again," she said. "Hand me that towel and let me see how you look all trimmed up." I gave her the towel, and stood with my arms and legs spread a bit, as if to say "Ta da!" "Very nice," she said. "You're getting into this, aren't you? Good! Now come over here and kneel on the couch, babe, looking out the window." She spread the towel on the couch just before I knelt on it, and I faced the window that's behind it. "Open those legs a bit more," she said as she caressed my ass cheeks. "Yes, very nice," she said, extending her gentle rubbing between my legs to include my balls and cock. "Such a nice package you have here, Rob."

She then picked up a small bag that was on the floor by her feet and pulled out the smallest butt plug and tube of lube we purchased together on our last date. "Your turn to wear this, babe," she said, dangling it in front of my face. "Let's get you ready for it. What you did to me worked pretty well, so pull those cheeks apart for me." As I did, she moved off the couch and knelt behind me, leaning in and licking up the length of my butt crack. I was already beginning to get hard again, but this attention made things rise a bit quicker.

She reached around and took hold of my cock while continuing to lick from my balls to my asshole. "Yes, you do like this. It's nice how you show me what you like," she said while squeezing my stiff cock, then stroking it slowly. She licked around my asshole more and began to push her tongue hard against it, then into it. The feeling was like nothing I had felt before. I pulled my ass apart as far as I could and pushed back against her mouth, moaning softly. She pulled on my cock and squeezed it while moving her tongue in and out of my excited ass. I loved it!

Then she let go of my cock and pulled her mouth off me. I groaned a little with disappointment. "Don't worry, we aren't done yet," she said as she put some lube on my ass and rubbed it around my hole, then dribbled some more on as she pushed her finger inside me. Again, she worked it in and out and twisted it around. When I was pretty well lubed up, she pushed her finger partway in, pointing toward my cock, and started to gently stroke my prostate. Her other hand held my erection and pushed back toward the finger that was rubbing my swelling glad. I was unconsciously moaning and pushing back against her finger. "That's it, you seem to like this a lot. Tell me," she said.

"Yes, I do like this, a lot. I've never had this done, not like you're doing. I hope you liked it that much when I licked you. That finger must be something like when I rub your g-spot. I think you're gonna make me come pretty soon."

"I've been reading about prostate massages. It's your p-spot, and it could make you come even without paying any attention to this nice cock, yeah, kinda like you did with my g-spot. But, we don't have time for that now, and I don't want you spill your load, yet." Suddenly, she again withdrew the attention of both hands and left me dripping precum. She noticed it and wiped her fingers across the tip of my cock, gathering the liquid, then put those fingers in her mouth. "Mmm, that's nice too. We'll have lots more of that later."

She showed me the plug again, then moved it behind me, lubed it up, and pressed it against my yearning anus while taking hold of my cock once more. "Spread your cheeks and bear down a bit while I slip this little toy into your bum, babe." She twisted the plug back and forth while she gently pushed it in. As it got wider I felt my hole stretching, it was a little uncomfortable, but I wanted to feel it in me. Finally it popped in, suddenly, and the discomfort faded into a new feeling that was a bit odd, yet sorta sexy. She patted the end of the plug, then, as I let go of my ass, she patted and rubbed my cheeks, giving one a kiss. "There you go. Now we're almost done," she remarked. Almost done? What else is there, I thought.

"Stand up and look at me," she instructed. As I complied she reached back into her bag and brought out a small, bunched up red cloth. As I watched her, she took it between both hands and displayed a band of fabric with a sort of pouch hanging from what I assumed was the front and a single thin strap that attached it to the back of the top band. "I want you to wear this tonight, too. It's all the underwear you'll need. Put it on, please." I looked at it a bit incredulously, but I took it from her and complied, then stood again in front of her. My now semi-erect cock was just showing out the top of the pouch, and I could not adjust it to get everything inside. As I tried to do so, she said, "That's what I expected, when you get aroused your dick will peek out. I bet when you get fully hard the whole head, at least, will stick out, and the waist band might be rubbing on that sensitive spot just below the ridge. Won't that be interesting? And, I got one with a single strap in the back so it rides up your butt crack, for a little more stimulation that I think you'll appreciate. How does it feel right now?"

"It's all very..., interesting," I said with a pause before the final word. "So far, you're doing a great job of playing with me and my comfort zone."

"Good, but we're just beginning and the night's young. One more thing for you to do before putting on the rest of your clothes, she said as she stood and hiked up her skirt some, showing a little black thong, which she pushed down until it dropped on the floor. "All this got me a little worked up, too. You need to eat me before we go, and you'll finish it this time, not like before our last date," she continued as she moved one foot out of the thong and sat back down, with her knees spread wide apart. Pointing between her legs she said, "What are you waiting for, come on and get me off." I quickly moved in and dropped to my knees before her. "Get on all fours and keep that cute ass up where I can see it. You don't need your hands, just push your mouth in here," she instructed.

I did as she said and started to kiss the inside of her thighs, but she corrected me, "That's nice, but you just need to lick my pussy, and then start sucking my clit. I might want a couple fingers inside to rub that special spot, but I'll let you know." And I went to work in earnest. She was wet and it tasted wonderful. I wished my tongue was longer to really get inside her, but I pushed my face in as tight as I could to go as deep as possible, and she moaned her approval.

I licked up and down between her clit and her opening until she signaled me to concentrate on that swollen bud at the top of her pussy by holding my head right there. I circled it with my tongue, ran the flat of my tongue across it hard, and sucked on it with my lips. She moaned more, squirmed some, and pushed into my face as she pulled my head into her crotch. "Right there, keep doing all that, just like that, oh yes, eat me, make me come on your face," she kept encouraging me, nearly babbling, and it really turned me on to hear it. As best I could tell, trying to look up at her while my face was buried in her sex, she had her head back, and I imagined her eyes were closed, as she concentrated on her impending orgasm. My cock was now pretty hard, and was definitely poking out the top of the red satin pouch. As she predicted, the waist band rubbing my frenulum, below the head, and it was stimulating, making me harder.

After a little while more, she came. Not really hard, but she did tense up and quiver a bit while she pulled my head into herself with more force, and then pushed me away. "Hmm," she sighed, "that was nice, you did well, babe. I hope you enjoyed it, too. Stand up for me. Oh, I see you did enjoy it," she remarked as she looked at the head of my cock proudly poised above the pouch and leaking precum again. "Come over here and let me get a better look at that." I stepped right in front of her and she reached out to wipe the fluid off the end of my swollen cock head, making me shiver a bit. "This time it's for you, open your mouth," and she inserted her gooey fingers for me to suck on. "Do you like that too? I sure do, and I like seeing you taste it."

I sucked her fingers and teased them with my tongue. She really is hot and can easily get me going. I really wanted her to be sucking my cock right now, but this was her night to call the shots. "I can't say that I like it nearly as much as I like your delicious juices," I replied, "but knowing it arouses you makes me happy."

"Well, now you'll be able to smell, and maybe taste, my juices on your mustache and beard all night I think, that should be nice. Ok, you should go finish dressing now. Those nice kakis you were wearing earlier and a clean button down shirt will do fine. Oh, and a tie I think, in case I need a leash of sorts, one that's outside your pants. Leave your wallet here, you won't need it and it spoils the look, and feel, of your ass in those pants. Scoot, now, I'm getting hungry." So I dressed and we went out to the car.

"I assume since you told me to leave my wallet that you'll be driving the car, as well as the rest of our activities," I commented, a little bit teasingly as I walked to her car and opened the driver door for her.

As soon as we were both seated she said, "Before you buckle up, I want you to undo your pants and hook the top of your so-called undies down below your balls. I want to keep an eye on you, and maybe a hand as well, from time to time." I did as she asked, remembering that I had made her expose her pussy as we went to dinner last time. As she might have been on that occasion, I was bit nervous, outside my comfort zone, but I was also getting aroused. My cock had relaxed, but was now beginning to enlarge again. She took notice and smiled approvingly. As we drove, she cupped my balls and caressed my cock occasionally. Her car was an automatic so she had more time to play with my stick instead of the transmission.

As we arrived, and she parked, she noted that I was leaking again. "Hmm, you're oozing again, babe. Be a good boy and wipe it all up, then put it in my mouth." As I took hold of myself and scooped the precum onto my fingers, she cupped my balls again, and said "I think these ought to be pretty full by the time we get back home." She opened her mouth and I placed my fingers inside, while she returned the attention I had had given hers earlier. "Such a nice appetizer," she said after I slid my fingers from between her lips. "OK, make yourself presentable for the public and let's go inside." She took her purse and got out as I fixed my pants.

As we walked across the parking lot, Jill put her arm around my waist, and I suddenly noticed that those wedge sandals had indeed made her a few inches taller than me. Just before we got to the door, she slid her hand down to the center of my ass, and kept it there. We entered the restaurant, which was dimly lit and just starting to fill with the Friday night crowd, some of whom were waiting, and watching us go by. Jill had a reservation and spoke with the girl up front, saying she had asked for a rather private table, for a special evening. As our waitress led us to the table, Jill was whispering to her. I missed most of the conversation, but I heard her make a dink order for the both of us, which I thought a bit unusual. When we got to a round booth in a back corner the waitress commented that this should be what we needed, and I thought I saw her wink at Jill, who was now close beside me again, with her hand back on my ass. I'm sure the waitress looked me over a bit, and she smiled at me, sort of knowingly I thought, as she turned to walk away.

"I've ordered drinks," Jill said, "and I let the girl know that we are on a very special date. I'm really going to enjoy this, and I hope you will, too."

"I'm out with a really sexy lady who knows how to show me a good time, so I think I'll be happy with the way things turn out. I'm not quite sure about how relaxed I'll be during all of it, though."

"I don't want you to be too relaxed," she responded, "I want you aroused, and maybe somewhat on edge. If you aren't yet, I think you will be before long."

We sat next to each other in the middle of the curved bench seat. Jill said, "You need to open your pants again. Be sure to undo your belt, too." I looked at her with raised eyebrows. "I arranged for a private booth like this for a reason. The waitress knows we may get 'affectionate' tonight."

I wondered what she had told the young waitress, but I undid my belt, unzipped my pants and had just undone the button and opened them, when she returned with our drinks. I quickly put my hands in my lap to cover myself, even though we were across the table that should have been blocking any view. But Jill said to the waitress, "Just hand them to my big cutie, please, and put down a couple cocktail napkins if you would." I had no choice but to move my hands to take both drinks. I think I was probably blushing a bit, so I was happy it was dark. The waitress smiled and handed me the drinks. Then said she'd be right back with menus. I wondered what she might have seen.

"You're not embarrassed are you? She couldn't see anything. Now open your pants some more for me," Jill said softly, but firmly. I did so, and she rubbed my crotch, making me start to grow. Then she leaned in and kissed me as the waitress returned with the menus, her hand still rubbing my new red pouch and its contents. "As I said earlier, it's a special evening and we'll probably be very affectionate," Jill said to the waitress, "you don't mind do you?"