Neighborhood Harem

Jenn gave a little yelp, and I was worried that I had done something wrong.

"Let's take this to my room," Jenn suggested.

I just stood and reached to help her off the couch.

We hurried upstairs like teenagers and closed the door to her master bedroom, and immediately started ripping clothes off each other. There was a trail of a shirt, pants, and a dress leading to her bed.

We were both lying on top of her covers, dressed only in our underwear.

I caressed her soft, round breasts which were encased in a lacy white bra. In between the lace, I could see the darkness of her erect nipples.

Jenn was rubbing my engorged cock through my underwear. "Oh my," she said. "This is much bigger than Rick's. It is going to feel so good when you put it inside me."

I ran a hand behind her back and released her bra, and then pushed Jenn onto her back. I was up on one elbow and pulled the bra from her and said, "Your breasts are beautiful."

I then leaned down and put a nipple gently into my mouth, moving my tongue around the outside.

With my free hand, I pushed down her panties which she kicked away. I ran my hand briefly over her pussy and dipped one finger to run along her slit. I felt the moisture which made her pubic hair wet.

Jenn let out a moan, as I kissed my way down her belly. She spread her legs, but I didn't take the immediate invitation to dive into her pussy. Building anticipation had always been important. I kept kissing down her legs to her feet, which I massaged and licked her toes.

I repositioned myself at the bottom of the bed and then started kissing my way up between her legs. With my hands, I pushed Jenn's legs apart and back which exposed her pussy wide to me. I nibbled on her inner thigh and then brushed my nose up her slit. This elicited a frustrated moan from Jenn.

I gave her a long, slow lick then from the bottom of her pussy up to her clit. She was wet and pulsing with anticipation.

I licked a finger, and then pushed it into her pussy while giving periodic licks to her pussy without pushing too hard on her clit, as I sensed that would push her over the edge. I pushed a second finger into her sopping pussy while giving her clit a bit more pressure. Jenn started her first orgasm, which I felt as she contracted on my fingers and leaked her girl cum into my mouth.

I didn't make a move to go up, but let her orgasm pass and then started my oral play again.

At first, she made motions for me to rise and then just gave into the pleasure of the oral attention. I didn't take as much time on my second pass, and was aggressively licking her while I held her legs behind the knees.

Jenn screamed out her second orgasm and pulled my head into her honeypot to apply pressure to her needy cunt.

I rose with a glistening face and went to give her a kiss.

Jenn recoiled a bit and reached over to her nightstand for a tissue to wipe off my face.

"Rob, that was awesome," she cooed. "Rick rarely did oral and never that good or for that long."

Jenn reached down to pull down my underwear. I helped her by raising my bum from the bed. She grasped my member and said, "This is going to feel so good. You have warmed me up and now you are going to fuck me so well with this big dick."

She swung a leg over my torso and guided me into her juicy hole.

As she descended my shaft, she kept making little grunts, and said how amazing it felt. Once I was fully sheathed in her pussy, she slowly started to rise and descend. I tried to meet her strokes to get maximum penetration. It felt great, but I must admit, that I was used to more control and wasn't sure I could get off this way.

To get her closer, I cupped both of her butt cheeks with my hands, to help guide her down my shaft.

Once we got a rhythm, I chose to spice it up a bit and let a hand wander to the crack of her ass and ran my fingers over her anus. On the second pass, I put a finger into her ass up to the first knuckle. It was something Susie had loved, and I thought Jenn might appreciate it as well.

I felt her orgasm start as her passage contracted on my cock and she yelled out again. After she came down, she pushed my hand that was on her ass away.

I pulled Jenn close and rolled Jenn onto her back while staying lodged in her pussy. I gave her a kiss and then started flexing my hips to pump my cock into her.

"You are insatiable," said Jenn, in a husky voice.

I picked up my pace. Jenn screamed out once again in orgasm, and this finally sent me over the edge. I groaned and relaxed and slipped out of Jenn.

On my side, I draped an arm across her belly and caressed her breast.

"That was the best sex I have ever had," Jenn said. "With Rick, it was fifty-fifty if I would even have one orgasm. I just had four."

"This is just the half-time show," I said, as I moved my hand to her breast.

"Rob, I am not sure that I am up for a second half tonight," she said, with regret. "You are so much bigger and I am a bit sore after that pounding."

"There are other things we can do that don't involve my cock in your vagina," I said, as I stroked her breast.

"Oh, Rob," said Jenn, as she turned away to her side. "Just go to sleep like every other guy."

I said under my breath, "I am not like every other guy."

_____

When I woke up in the morning, Jenn was up and just coming out of her ensuite bathroom with a towel around her head and nothing else on. She had a great body.

"How are you this morning, Mr. Big," Jenn asked, with a smile.

I lifted the sheets and made a show of looking down and said, "Still pretty big."

Jenn was now by the bed and laughing.

I reached out and grabbed her waist and pulled her onto the bed as she squealed.

"Yes, I am still big, and we are going to have to do something about that," I said, as I pinned her down on her back. "But before we deal with that, I think I need some breakfast. I had a fine meal last night, and believe there might still be leftovers."

I gave her a quick kiss and then moved down her body, stopping briefly at her breasts for some oral attention. I then made my way to her pussy. Her pubic hair was still damp from the shower and was now getting damper with expectation.

I dove in and Jenn's giggles turned quickly to gasps, as I ran my tongue around her outer labia.

Jenn spread her legs wide and grasped them behind her knees to give me similar access to last night. I ran my tongue from her rosebud up to her clit coating it all with a heavy layer of spit. I put my index finger in my mouth and then pressed it to her ass.

I had thought that she secretly liked this, as it had sent her into an orgasm last night. She had also sent the signal that didn't want it by pushing my hand away.

I looked up, and she raised her eyebrows in question, with my finger applying gentle pressure. She shook her head in refusal, so I moved it up to her vagina and kept up my oral intensity. When she was close, I pulled my face back and stopped moving my finger.

Jenn let out a frustrated moan, as I smiled at her. She tried to grab my head, but I was able to dodge.

I then blew lightly across her pussy lips which made her shudder. I then slowly resumed licking until I brought her to an orgasm, as I had my mouth clamped to her pussy.

"Oh, my fucking god, that is amazing!" she yelled.

I crawled back up next to her with my glistening face.

Jenn took the damp towel from her head and gave my face a wipe before giving me a kiss. As she kissed me, she reached down and grasped my cock and started to stroke me.

I laid back with the expectation that she would now give me a blowjob.

That didn't seem to be happening, as she just continued to stroke me.

My hand was on her back and applied a little bit of pressure to indicate what I wanted.

She then, hesitantly, moved down lower on the bed and used the towel to give my cock a quick wipe. I suppose she didn't want to deal with any residue from last night. This wasn't something that had bothered Susie, but I had to respect differences.

Jenn then resumed her stroking and would give a quick, tentative lick to the head.

It had been so long since I had sex other than last night, I was still not going to last long.

Jenn got a bit bolder and put the head of my cock in her mouth as she kept stroking. It felt great and the sight of her doing it, started my orgasm.

As my first stream shot into her mouth, she instantly recoiled from my cock with the second stream hitting her from nose to chin. She opened her mouth and spat out the cum in it and looked up at me with venom and said, "What the fuck was that?"

"What do you think it is?" I said, with disbelief. "You are an adult and have to know the basics of how a male orgasm works."

"But you just came in my mouth!" Jenn yelled. "That is so disgusting. You are supposed to let me know so I can get it out before you cum."

"Jenn, I am sorry," I said. "I didn't know that was your expectation. You have to realize that this is the first time I have had sex with another woman in over twenty years."

"Well, that isn't happening again, ever," Jenn said, as she wiped her face with the towel.

I stewed for about a minute and then thought fuck it. No sense stewing on this, time to get it out on the table.

"Jenn, I think you have a bit of a double standard," I said.

"How do you mean, Rob," she said, with some anger in her voice.

"Between last night and this morning, I have gone down on you twice which resulted in you cumming in my mouth three times," I retorted. "You even pulled my head into your pussy as you orgasmed.

"Now don't get me wrong, I loved it and I loved giving pleasure to you. I had no problem with it. I just don't see how it should be so different when the roles are reversed."

"It is totally different," she said, unreasonably. "Good girls don't swallow."

"Well, I think that is an outdated idea," I said. "I guess that maybe I am not looking for a 'good girl'"

"Yes, maybe you should go and take your perverted ideas with you," Jenn said. "I hope you find your cum-swallowing anal slut."

I laughed at her attempt at a carve and said, "I hope I do, too. Since you brought up your disgust for anal, you might want to remember what set you off on your orgasm when you rode me last night. Your mouth said no, but your body was saying yes.

"Think about that when you find a guy who just shoots his load and rolls over.

"Oh wait, you won't have to think too hard imagining that, as that is the person you just left."

I got up and started pulling on my clothes, as Jenn was fuming on the bed.

As I finished getting dressed, I went over to her and sat on the bed. "I am sorry that this isn't working out," I said. "I went into this with every hope that it would. I hope you know that I have not tried to deceive you in any way."

Jenn still didn't say anything.

I got up and said, "I am sorry again. You are a beautiful lady and clearly, we just aren't compatible in bed right now."

I got up and went to her bedroom door where I heard footsteps just outside.

I let myself out of the bedroom and headed downstairs to find Samantha in her pajamas in the kitchen. She looked up and gave me a smile which was probably half genuine and half out of guilt for eavesdropping on us.

"Hey, Samantha," I said.

"Hey, Mr. Smith, do you want some breakfast?" Samantha offered.

"Call me Rob, and thanks for the offer, but I think I should go," I said.

"Too bad it didn't work out," Samantha said, quietly.

"Yes, it is too bad," I agreed. "We are both adults who don't want to go down a path where neither of us will be happy in the end."

"I understand," said Samantha. "Good luck on your search. You are a nice man, and you're going to make someone very happy. Say hi to Jordan and ask her to give me a call when she gets a chance. I enjoyed spending time with her this summer."

I took my leave and headed home.

I checked my phone when I got in and saw a few messages from Jordan. She was looking for an update on how the date went.

I texted back: "We had dinner after the party which went well. The after-dinner stuff didn't go as well."

My phone dinged with a reply in seconds, "You are going to give me a LOT more details."

A video call from Jordan then came up. It was time to face the music with my daughter.

"Dad, well done on going on a date!" Jordan gushed. "You are not getting away without describing the juicy parts, though."

"I am not sure that I am comfortable sharing that and especially with my daughter," I said.

"Dad, get over it," Jordan said. "I am an adult and fully aware of all aspects of relationships. Hell, it is what I am studying."

"Yes, but you are my daughter, not my therapist," I argued back. "Intimate details shouldn't be discussed with your children."

"Dad, that is so old school," Jordan said. "And I have news for you. My old bedroom at home shares a wall with yours, so I have been aware of all your intimate details for years."

"You listened in on mom and me?" I said, with shock.

"All the time," Jordan said. "And I will say it was very sexy. When I was old enough, mom and I would talk about it after you left for work. You had a great thing going and made me very liberated about sex in my own life. So don't think that anything you are going to describe will shock me."

"That is a lot to process," I said.

"Okay, we don't have to get to juicy bits right away," Jordan said, with patience and a knowing smile. "Tell me about the party and dinner and then you can spill your guts about the rest of the evening."

I told her about the party and how Jenn had latched onto me right away. I also told her about my brief conversations with Erin and her blatant propositioning.

"Erin is clearly a wild one," Jordan commented. "We knew this, but her submissive gestures in public are eye opening. You know that the silk band that she was wearing denotes her submissiveness. Touching it would have been a big turn-on for her."

I moved on to talk about the dinner and the open conversation that we had about me staying over.

"That is a good conversation to have while you are dating," Jordan said. "You want to set clear expectations and ensure that you aren't misinterpreting her signals. So now we are at the meaty part. Time to give me real details."

I described our making out on the couch and then our quick move to the bedroom. "I was really enjoying myself and I think Jenn was getting a lot of pleasure," I said. "The issue was that the pleasure was not reciprocated."

Jordan pressed for real details, and I finally relented and described her ending the lovemaking in the evening, and her hesitation to provide oral and her subsequent disgust, "...with me blowing in her mouth."

"Dad, you did the right thing by expressing your disappointment with her," Jordan said, sympathetically. "Life is too short to put up with selfish lovers and bad oral. I do have one question. I know that you and mom did some bum stuff. Did you try that with Jenn?"

I relented all the details about that with Jordan. I really had no secrets left with her.

"I think that Jenn is just stuck in an old way of thinking," Jordan said. "She might come around, but I don't think you should go on that journey with her. Let's move on to your next prospect."

"So soon?" I asked.

"No time like the present," Jordan said, with confidence. "You have to get back on that horse and ride. Your first date wasn't that bad, it just wasn't perfect and isn't going to result in a longer-term relationship. To find someone good, you need a larger sample size to choose from.

I want you to message Erin and Heather by end of day tomorrow. It is time to get a couple of balls in the air now that you are back in the game."

"Yes ma'am," I said, as I saluted my new taskmaster.

"I have messages from Jess and Samantha," Jordan said. "Am I okay to talk to them? I will reveal some details to Jess. She deserves some juicy stories for all the work she put into this. Samantha is probably disappointed, and I will talk to her. She has had a rough time with her parents' break up."

"I am fine with that," I responded. "I will never hear the end of it from Kenji. He'll be relentless in his ribbing."

"Dad, you did well yesterday," Jordan said, with enthusiasm. "I think you will have a wild time with Erin and you should learn more about Heather. Let yourself go and don't be afraid to try different things. Your bum obsession is no longer frowned upon. It has gone mainstream, and most people are into it... I know I am. Go forth and prosper and don't forget to share the details."

"I will," I said, with confidence. "I am not sure if I am ready to hear your intimate details yet."

"Give it time, dad," Jordan said. "It will become normal, just like it was between mom and me."

We signed off and I headed to my bedroom to take a shower, do a workout, and then a dip in the pool. Jordan's pep talks and the workout cleared my head and by the afternoon, I approached the future with a new sense of optimism.

I sent three texts that afternoon.

The first was to Jenn, thanking her for the evening and saying sorry that our needs didn't match.

She responded with a brief acknowledgement, and finished with an apology of her own for being a bitch.

The second was to Heather, an old friend from school who had never been married. She was successful and had a killer body. I suspected that she had never found someone due to her lack of confidence. I suggested that we get together for a coffee.

Lastly, I took some time composing a message to Erin. She had indicated that she was submissive and had even made reference to me as 'master'. I messaged, "Time for you to get some prime rib. The secondhand burger meat was a bit rancid. You will come to my place for six tomorrow night. Dress appropriately and include the collar."

Erin responded in second with a "Yes sir! Should I bring an overnight bag?"

"I am disappointed that you don't know the answer to that question already," I replied. "You should bring anything you may need to be satisfied."

"I will come fully equipped. See you at six." Erin responded in seconds.

I copied the text exchange and set it to Jordan who responded with, "I love your assertiveness. It is what she wants, so play it up to the max."

I spent the afternoon buying some groceries to make a dinner for tomorrow. I also went to my bedroom and got out some of Susie's toys and fixed some restraints to the post of the bed and made sure I had a supply of lube. I had been a scout in my youth and always believed in being prepared. Getting set up had gotten me excited, but I held off indulging myself as I was going to need stamina for tomorrow.

Chapter 5

I took off early from work and prepared a seafood dinner. At exactly six, the doorbell rang.

I opened the door to find Erin dressed in a kimono. She had her red hair pulled back in a tight ponytail and she had a leather collar around her neck with a metal ring on the front.

"I am here to deliver the prime rib you requested. It hasn't been cooked yet, so you may want to put a leash on it," Erin said, as she handed me a black leather leash.

She stepped into the front hall, and I took the leash and her duffle bag.

I knew I had a role to play here, which was not natural to me, but was very intriguing. I walked around her and wasn't able to discern too much about her outfit, as the kimono hid much. As I got back in front of her, I reached around her back and grabbed the ponytail and pulled her head back. This exposed her neck, and I deftly clipped the leash to the ring on her collar.

"The meat needs to be more exposed," I said, as I pulled the bow apart on her kimono. I pushed it off her slender shoulders and fell to the ground around her feet.

What was inside, was spectacular. Erin was much slighter than Jenn, with elfin-like features. Erin had a matching set of black lingerie that left little to the imagination. Her pink puffy nipples sat atop firm B-cup breasts and were straining at her lacy bra which was semi-transparent. Like her daughter, she had a dusting of freckles on her face and shoulders. Her skin was alabaster white, other than the freckles. She had a garter belt on, to hold up her silk stockings.