A&C 11: Jenny Gives Billy His Wish

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Jenny gets into Anal with Billy with Alice's help.
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Part 11 of the 11 part series

Updated 04/05/2024
Created 11/24/2023
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11. Jenny Gives Billy His Wish.

This story is fiction and you are welcome to imagine the characters as you wish but everyone is 18+ at the time the story happens. Hopefully this is plausible. Issues such as STDs and family planning are considered outside of the narrative.

It starts during the end of the second wave of Covid 19 in England. It comes after a 01. Beautiful Spring Sunday, 02. The Next Morning, 03. Art of Customer Service, 04. Rumbled and Outcome, 05. Donna Exposed, 06.Thor's Story, 07.Billy Gets His Wish, 08. Spreading the Love, 09. Jenny Gets Her Man and 10. The Reformation of Billy.

You are recommended to read those first... But particularly 09.

[NOTE: This shares some narrative that is common with my One Off 'A Gift for My Valentine' as I was working on this when I realised that I could borrow from it for that story. I could have spent more time camouflaging the self-plagiarism, but it would not have added anything to this story. However, the events are not directly lifted, but edited to suit. So apologies if you see "I know you get randy about now, but you seem extra keen and orgasmic. Care to share?" and think 'I read that before': You have.]

----

Jenny here as this is my story. If you haven't read Jenny Gets Her Man, and earlier revelations you may have problems understanding what is going on, until it gets to the fucking.

I have moved into Fourways Farm and I am living with Billy in the so called Guest Wing, where Cal is now living with Al in the Family wing. Our sex lives are fulfilling but as two couples with not sexual interaction. Billy assures me that he doesn't miss sex with Al, or the sessions with her, and Cal.

Now I know, because we talk, that Al has implants and is one of those women who doesn't have much if anything in the way of a 'time of the month', where I do, though only for a day or two. Billy is understanding as he has never had so much sex, even more than with Al.

Now the only problem is that I get randy around the time that Billy can't help me. However, the other thing I have noticed is if we are having sex 'doggie style', his thumbs creep into the crease and he tends to pull on my rosebud. Now I find that stimulating in a way that gives me better orgasms.

So, one time I asked. "Billy, have you ever done anal sex?"

He looked a bit embarrassed. "Yes, but not lots."

"Did you have it with Al?"

He actually blushed. "Er, yes, twice actually, but I don't think Al really likes it."

"Do you want to do it with me? I think I might like it."

His smile was epic. "Really? Yes, I would, but I think you need preparation. Al had a, er, thingy, butt plug, and had lubed up."

I hadn't thought of that, if the porn I had seen men often just stuck it in, or put a finger in first. Though I had seen a butt plug being removed just before a man with an inhuman sized cock rammed it in the woman. Any lube seemed to be later. "Oh, I suppose it might be a good idea if she doesn't mind."

"I'm sure she won't if I know her."

----

So the next evening I met with Al as Cal was working a late shift at the airport and wouldn't be home until gone ten. I had told her it was that I wanted to know about anal sex, so she was prepared.

"Jenny," She said in a happy tone, though I have rarely known her anything but. "we need to meet more, but Billy has got you interested in anal, the naughty boy!" And she winked.

I felt a blush. "Actually, it was more me. He hasn't really touched me there, but the bit of attention he has done does something so I asked and he said I should speak to you as he knew you prepared for the two times he had done it with you."

Al nodded and smiled. "I'm glad he was honest, but did he say Cal was there both times and that as well as Billy in my ass, I had Cal in my pussy?"

My mind reeled, I had seen double penetration, but didn't think 'real' people did it! B but there again few have access to two men like Al did before I 'stole' Billy from her.

Al realised I was stunned. "Jenny, I am not suggesting that we have group sex." I immediately relaxed. "I was just giving 'full disclosure'. I didn't get much from anal, but the feeling of two men was special, but not something I was hung up on and I have a way to get a lot of the benefit without the bodies."

"Thanks for that Al, I won't be surprised if Billy lets something slip and in an odd way, it will make Billy having anal with just me, somehow more special as he didn't with you." I thought, but I suppose he has with other women, but not ones I know.

With that Al opened the box on the table and started to get things out. "These," She said laying out three blue objects that looked the same, but went from slim to fat, the fat one looking like a butt plug. "are training plugs, the thin one is the first one. When you are comfortable with that, putting it in, playing, taking it out and wearing for a while, starting with ten minutes then up to a couple of hours, you move up to the middle one. Then when ready, you move up to the last one and then you will be ready for this one."

With that she brought out a metal one with a jewel in the base and it was bigger again. I asked. "Can I pick it up?"

"Of course." So I picked them up and felt the difference between the largest trainer and the jewelled one. "You will see how much heavier it is and you really feel it when you wear it for any time. Apparently some women like it so much they wear one most of the time, but not my cup of tea."

I wondered what it would feel like to have that in me and was almost too anxious to start. "I don't suppose I could borrow these?"

Al shook her head. "I don't think we should share them, but I will share the links and you can have them next day delivery. They aren't that expensive." I nodded and understood, I would never share a vibrator and these were more intimate.

She reached in the box. "Now moving on, you may want to practice with one of these." She brought out a short, narrow, black, knobbly dildo and passed it to me. "This is exactly what it looks like and once you have practiced with the plugs this can be quite nice, if anal is your thing, so I understand, but it doesn't do very much for me."

I passed it back. "Right, anything else in your box of wonders?"

"I haven't mentioned lube and you will need plenty of it," And she got out a couple bottles and tubes out. "or I did. But saliva might do it for you if Billy really works at it. However, you will need it, or oil, for the plugs and dildo, I'll give you the links for them as well. If you fit the plug, you can ease it out and then lube up the gape, and put the plug back so that you are well lubed when Billy takes the plug out." She added, with a smile, clearly remembering her experience. "He seems to know how to play with it and your pussy before he removes it."

I felt that I was learning a lot but also that Al hadn't finished, the mental images were turning me on and I felt warm and wet between my legs. "What's next?"

She took a deep breath. "Right, some people think this is being over the top, and others that it is vital, so make your own mind up." With that she brought out a black bulb with a fine nozzle and a pack of intimate wipes.

"What's that?" Referring to the object.

"Right, I'm not trying to put you off the idea, but I had to think about Cal and Billy as well as me. It's an anal douche, for giving an enema. Read the leaflet that comes with yours on how and when to use it. Basically it assures that you are clean back there. Also some men will switch between ass and pussy, either deliberately or by accident, and being clean is a good idea."

"I'll get one and think about it. Anything else?"

"Right, confession time." Al said with a deep breath. "I wasn't really into anal, but double penetration was special, particularly feeling so full and also the feeling of a cock in my pussy moving against something in my ass." I must have pulled a face as I wondered if she might want to borrow Billy, so she added quickly. "But I don't want to be with two men again. So, this next item is more expensive than the rest together, but I don't think you will need one."

She reached in and brought out a black butt plug, but it had a T-shaped handle, and then a small black oval thing with buttons. She pressed one and the plug started to buzz and move on the table.

I looked at her and guessed. "Remote control vibrating plug?"

She smiled and patted my hand whilst switching it off. "Got it in one. I get the feeling of being full and also it adds something, but I use it more in solo play with a dildo than with Cal, but we have used it together and he controls the remote."

"Ok, but I don't think I will need that. Well not straight away."

"I agree, but you might want to experiment with a realistic dildo or vibrator to experience the DP effect and I'm sure Billy will love it as a treat for you both." With that Al started to put everything back in the box.

I thanked her and we had a hug and Al sent me the links and I went on line, ordering the training plugs and lube first of all, but I went for a glass ones with ridges as they were described as being more stimulating and looked much prettier, not that I would be putting them on display. Then I had, not much persuasion needed, get Billy to fuck me as I had got turned on by my chat with Al and the idea of the toys I had bought on line.

----

I started with the first one and to get me in the mood, I first of all, brought myself off with my favourite rabbit vibrator. I got on my knees and lowered my head to the pillows, but got in a position so that I could see my bottom in the wardrobe mirror. The wardrobe filled one wall, parallel to the bed and had three sliding doors which were mirrors from floor to ceiling, so we had watched ourselves making love many times.

I then gradually eased the well lubed plug into my rosebud. At first I could hardly get any of it in, but it felt interesting and then I touched my clit and relaxed and it went further in, so I played with myself more and then it suddenly slid all the way in. I realised that I liked the feeling and started rocking it and pulling it out and in and suddenly had another orgasm, which felt different, and then pushed it all the way in and left it.

I got up and walked around feeling the weight in my rear. I then went to the ensuite and had a quick shower, just below my waist, and I eased out the plug and got a hint about the advantage of an enema.

So back online and ordered up the enema kit and picked two full sized plugs, a smooth metal one and a sculpted glass one, to save on delivery.

----

So, I worked up from the first plug, through to the second and the third, taking a day or two with each one. I had to find enough time whilst Billy was out and he nearly caught me one time. I always started with getting an orgasm from my rabbit but by the end I was having an orgasm just from playing with the plugs.

On Friday I was able to put in the metal plug at the end of the day, and leave it in until bedtime, but I removed it before Billy and I went to bed, I wanted to surprise him on Saturday evening when he thought I would be 'off bounds'.

However, as we were cuddling and kissing he said. "I know you get randy about now, but you seem extra keen and orgasmic. Care to share?"

I think I blushed, but the lights were low so possibly he didn't see, but I still dived under the covers to take his cock in my mouth. He groaned and ran his hands lightly through my hair. "Good way of avoiding the question. I'll wait until you tell me."

----

On Saturday morning, we didn't make love as I was wearing underwear overnight, so Billy didn't expect anything would be happening for a couple of days. I was always willing to give him a blow job, but he felt it was unfair on me that he got more than me.

During the day I put in the metal plug so I had been wearing it for a few hours before bedtime. I got ready first and when Billy was in the ensuite I got out the training plugs and placed them on my bedside draws, along with a bottle of lube, so I did put them on display!

When he came out, I nipped back in and updated my preparations and switched to the glass plug and removed my panties as I was using a cup, another innovation in the name of our sex life, and entered the bedroom naked. The thought of what I was doing was turning me on and I was starting to feel warm and tingly in my pussy.

Billy was standing naked by my side of the bed, his night clothes under his pillow. He was holding the largest of the training plugs like it as if it was the most precious thing he had seen, with a gleam in his eye. "Are these what I think they are?"

I smiled. "They are and I've had them a week. I think you will like the one I am wearing better." Well he nearly dropped the one he had in his hand.

"Are you...?" Clearly confused by my lack of panties.

"Yes, but I have a cup in, so you can play with my pussy while you fuck my ass." I have never seen his erection shoot up so fast. He grabbed me and we kissed passionately, with his erection wedged between us.

He was in a sort of daze so sat him on the bed. I spread his knees and got down between them and took hold of his shaft in my right hand and his balls with my left and started playing with him. Billy stroked my hair and I gently took the tip of is prick in my mouth, tasting the pre-cum that already started to flow. I licked along the underside of his shaft, then around the head and then I bobbed my head up and down enthusiastically.

Billy reached down and played with my tits, getting the nipples engorged and sending tingles through me. Oh I was getting so wet down there as I worked on his shaft and balls with my mouth and hands. I licked his smooth balls, he shaves for me, licked and wanked his shaft, sucked on the head, taking it as deep as I could and play with, swirling my tongue, and repeating it. In no time he was groaning and said. "Jen-babe, so good, I'm ... Oh!" And he came in my mouth as I intended, I wanted my first anal to last and also for Billy to be a bit relaxed when he first entered.

I got on the bed, parallel to the mirror and said. "Billy, play with me." He positioned himself to the side of my hip, as I found out later he had with Al, and played with the plug with his left hand. He reached under me with his right hand and played with my tits and pussy and when he put his fingers in my vagina I could see Al's point about a vibrator, but no time for that now.

Billy, worked wonders on me and I had an orgasm that left me dizzy. "Ohhh!!! Billy-Boy!!! AHHH!!!! FFFUUUCCCCKKKK!!!!"

When I looked at our reflection, I noticed Billy's prick was starting to rise nicely and so I said. "Bill-boy, I need you in me, so get that plug out of my ass and fill me with your shaft."

Billy's face beamed and he scooted around behind me and with his right hand he spread my buttocks and with the left he gradually pumped the plug harder and harder, rocking it as well, until it emerged from my sensitive rosebud, causing me to have another little orgasm. "Ooohhh! Sooo GoooooD!"

He wasted no time, using both hands to spread my bottom cheeks before my gape closed and directed the head of his shaft into me. I could feel the pressure of the head against my bud and then he reached round and massaged my clit and I melted and his shaft entered my back door and, because of the copious quantity of lube, slid half way in.

Billy continued to play with my clit and started to thrust in and out of my back door, sending thrills into my core that I had sensed from using the plugs. "Bill-boy, go for it, I need you deep in me, fill me, fuck my ass."

He grabbed my butt cheeks and pulled them wide and thrust all the way in until his balls swung forward and hit my pussy lips. "Jen-babe, oh you feel so good, I have never felt anything better, except your pussy."

I smiled, even if it was flattery, he knew I needed to hear it. "Bill-boy, Bang me, I know you are the best at that!"

Billy pulled back until he was nearly out and then rammed back in. Oh, that felt so good but different, especially the start, but then the end when he bottomed out, ramming into my bottom and squeezing my vagina.

I reached back and played with my clit. As Billy's repeated ramming continued, getting faster and stronger, my clit play got harder and then I reached in to my vagina with two fingers.

I got to my g-spot and hardly touched it before I climaxed and nearly lost consciousness. "FFFUUUCCCCKKKKKIIINNGGG!!!!! FFUUUCCCCKKKK!!!!! Fuck, fuck fuck bill-boy!"

My spasms must have triggered Billy as he shot his hot seed into my bowels and we slumped down onto the bed. He rolled off me and as his prick pulled out of my ass, leaving me gaping and feeling so empty and I groaned at the loss. Billy must have sensed my need as he gently eased the butt plug back in and then cuddled me.

"Bill-boy," I quietly said, turning to kiss him. "that was fantastic, and I am sure it will get better with practice."

"Jen-baby, I love you and I promise we will."

After we had our post fuck cuddle I went and had a shower and got myself ready for bed, without the plug and then Billy and I had another cuddle and went to sleep.

Over the next few days we had more anal sex each evening.

----

On Sunday night I got prepared the same way and I gave Bill-boy a blow job. He knew we would be having anal sex, but what he didn't expect was for me to lie on my back with my head off the edge the bed. He knew that when I was in that position I could, and wanted him to, deep throat me.

He enthusiastically got in position, but then gently offered his prick to my mouth. I kissed the end and sucked him in. When he had just the head in I could run my tongue around the whole tip including the underside and soon I had Billy groaning. He let me control his movements with hands on his hips whilst he played with my tits and nipples.

Inch by inch I worked him deeper into my mouth until he was reaching the back of my throat. I eased him out, took a deep breath, relaxed my throat and pulled him right in until my throat bulged, my nose was nestled in his balls and my chin was on his pubic bone. I let go of his hips and he slowly fucked my throat.

"Oh Jen-babe, this is so wonderful, I love you so." I wished he could just keep going but I had to touch his hip, our signal, and he withdrew to let me breathe, leaving just the head in. Saliva was dripping off his shaft and running up my cheeks, and Billy used his thumbs to wipe it to prevent it getting in my eyes. Oh, how he had changed from the Billy the Bang I first knew to this masterful lover who would give me anything I wanted. I knew it was thanks to Al and Cal that he had changed, and I quietly thanked them in my heart for that.

I mumbled around his prick. "Bill-boy, anything for you, everything for you." Then I swirled my tongue around the head and took a deep breath and then he smoothly slid his prick all the way in again and again, face fucking my throat until I touched him again and he let me breathe and wiped my eyes, before going in again.

This time he reached further down my body and started playing with my pussy, thumbing my clit and probing my vagina, finding my g-spot. I let him have my throat for as long as I could but had to touch him as my orgasm flowed through me. As I was nearly out of breath, I could only sigh happily but I could feel how wet my pussy was.

He was waiting with the tip in my mouth as I recovered my sanity, and I don't know why letting him have his way with my throat is such a turn on. I rolled over and, supported on my elbows, began to work on his prick with my right hand on the shaft and left on his balls. I bobbed my head and sucked and worked my tongue on the underside of his shaft, using the tip to pleasure the web below the head.

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