The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me.
Sissy and Paul
Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the ‘older generation’ or people who wanted a bit of quiet/privacy.
We had married several months earlier and found a place we could afford to buy next to an Old Folks Retirement Centre – it was what they called ‘Warden Controlled’ this meant they residents had their own accommodation but there was always someone on call for emergencies.
One Friday we went to the local pub and decided to drink in the Snug as Sissy was feeling a bit down having had some bad news and didn’t want to sit in a noisy atmosphere. As it happened this was a good choice, although we didn’t realise at the time.
When we went in we found it occupied by 3 guys from the retirement centre, so we sat over in the opposite corner.
One of the guys said good evening and asked if we were the couple that had just moved in to the house next to their centre, we agreed that were and one of them offered to buy us a drink as a welcome to the neighbourhood. During the night we ended up sitting with them and having a great night.
Joe was 78, 6’3”, widower, ex miner. Pete was 75, 5’11”, widower, ex miner. George was 72, 5’6”, widower, ex shop manager.
Sissy was 19, 5’1” – 36B-32-34, blonde shoulder length hair, very pretty, sparkling blue eyes. Paul (me) 21, 6’0”, average guy
Over the following few months we got in to habit of joining them rather than going in to the main bars as we knew no one else locally. Sissy flirted with them outrageously.
One week we had go to visit Sissy’s parents and didn’t get in until about an hour later than usual and the guys gave us a bit of a ribbing over being late, Sissy said in a teasing way “Ah! Did you miss us then boys”. Joe replied in the same manner, saying that she was becoming very cheeky and she should have far more respect for her elders.
Sissy laughed and asked what he was going to do about it. At this Joe replied saying I’ll have to think about that. When Sissy went to the loo, Joe asked how far they could push the teasing with Sissy, I said as far as she lets it go, she would tell them if they went to far. Joe then asked how I would feel about them teasing her, I said providing no one got hurt I would accept most things and that I would also tell them if I thought they were going to far.
As we walked home that night we got level with the centre and Joe said to Sissy “I’ve thought about what to do about your cheekiness young lady, and if your not careful, we just might have to slap your butt” Sissy laughed said “Yeah, Yeah, Yeah, when your big enough” then danced out of reach and we went the rest of the way home.
The teasing went on like this for weeks, all of us enjoying the interaction.
It was a late Indian Summer night and Sissy was dressed in a short flaired skirt, a boob tube (no bra), white French cut knickers and 4 inch high heeled shoes, she looked stunning. When we went in to the snug the guys all stopped talking and looked at her with astonishment.
Sissy asked what was wrong, George said absolutely nothing, you look fabulous girl. We got our drinks and sat down. We could hear the music from the other bars and George asked me if I would mind if he had a dance with Sissy, I told him it was not my choice and to ask Sissy. Like most girls back then Sissy could do all the old dances, as well as the new stuff, at the end of the dance George bowed to and said thank you, Sissy curtsied and said my pleasure, as she dipped down the skirt flaired out slightly,
not enough to show anything, but all the guys stared down towards her legs. All 3 had several dances during the rest of the evening.
When we got home Sissy nearly dragged me into bed, horny as hell and almost dripping wet with excitement. We had a fantastic session making love. I asked what had brought on the horniness and she said that guys reaction to the way she was dressed, all the compliments and dancing with them had made her feel really good about herself.
The next week she wore a Rah-Rah skirt and a tee-shirt that she tied in the middle of her waist so it showed most of her midriff. The guys again showed their appreciation with comments of how good she looked and hoped they would be able to dance again. I noticed that the tables had been moved around to make a bit more space.
When dancing Joe spun Sissy round which caused the back of her skirt to lift showing up to the bottom of her butt cheeks., George, Pete and myself watched with interest to see if we would see anything more, but alas the song finished, all of us danced with Sissy during the rest of the night, I think it became a competition to see who could get the skirt up the highest with the others watching.
Eventually Sissy said something cheeky in response to a remark Joe made and he said careful girl I’ve not forgotten what will happen to you if you keep being cheeky, Sissy said again Yeah, Yeah, Yeah, and went to go to the loo, as she got to the door she flipped the back hem of the skirt slightly and flashed a view of the bottom half of her tight, cute little butt. All stared open mouthed at her retreating back. As she came back in the landlord called time (drink up and go home time) so nothing else happened.
When we got home we made love with a passion, I was beginning to enjoy the ribaldry more and more. I asked Sissy what she would do if they kept their promise to spank her, she laughed and said don’t daft, their all mouth and trousers and wouldn’t dare, I asked again what she would do and she said again they wont, besides their to old to do anything and follow through. I wasn’t quite so sure, but thought it might be fun to watch if they did and I liked the fact that Sissy seemed to becoming a bit of an exhibitionist.
The following week Sissy wore a dress which was slightly longer than what had become her normal attire, I commented that the boys would be disappointed in that. Sissy then did a spin and the bottom hem lifted up showing a goodly portion of her knickers and if she spun around fast enough the hem would go level with her waist exposing her entirely from the waist down.
When we got to the pub the Sissy greeted them by saying something along the lines of, “Well if it’s not the 3 wise old monkeys – hear, see and say nowt” and asked if they wanted a drink, they all said yes, so Sissy went to get them. Joe said that she was getting cheekier and that they might have to carry out their threat. I just laughed and said nothing.
Sissy came back with the drinks and asked who was for the first dance. As a rock and roll song came on I said I was. As we danced I gave Sissy a spin lifting her arm up high and the dress flared up high. All three of the lads looked stunned at the sight before them, so I spun Sissy again. Suddenly Sissy stopped dancing and nearly fell over laughing so hard. I asked what she was laughing at and she pointed to the lads and said “the look on their faces. I mean its not as if they haven’t been trying to look up my dress for weeks is it”. We all then joined in laughing.
As the night progressed they lads all danced with Sissy making sure that they made her spin round as often as they could and when not spinning her they were attempting to grope her.
When we got home I asked Sissy if she was comfortable with what was happening, in reply she came to me, saying that all three had felt her tits, and had put a hand on her bum, sometimes over her dress and a couple of times under it. As she was telling me this she stood in front of me and undid my trousers, reached in pulled out my dick and gave me a truly fantastic blow job, swallowing nearly all of my cum, then licked off any she had missed. We made love, for the first time in weeks, with a slow gentle passion, Sissy actually squirting as she orgasmed.
Nothing happened for a couple of weeks as we went on holiday and didn’t get back until about 8.30 on the Friday so by the time we had unpacked, we didn’t get to the pub until just gone 10 o’clock so only had time for 1 drink. The boys greeted us enthusiastically, shaking my hand and giving Sissy a hug and a quick grope of her bum. I had a feeling that they had missed her far more than they had missed me.
The following Friday Sissy wore a leather skirt that was about 8 inches long coming down to about an inch below her crutch and only just covered her when she sat down providing she sat still. It was fastened by 6 press studs down the front, but these tended to move round to the side as she walked, her top was her favourite boob tube, this was 3 inches wide and literally just covered her pert boobs, she had on knee length lace up boots that had a 4 inch heel.
We arrived at the pub to find that our drinks were already on the table, we talked for a bit about the holiday and what we had done and seen. George asked if Sissy’s sun tan was an all over one, she grinned and laughingly said “That’s for me to know and you to dream about big man”.
About 9 o’clock the band in one of the other bars started and as usual they guys took turns dancing with Sissy, her skirt being tighter than usual didn’t flair out like before so when Joe danced with her instead of just getting her to spin around, held on to her hand and lifted his arm so Sissy spun round underneath his raised arm, this had the effect of making Sissy stretch up raising the bottom of her skirt and nicely flashing her knickers to the rest of us. As usual we all took turns to dance with Sissy, each of us making sure to get the skirt as high as we could.
Pete went to get a round of drinks in, as he came back, Joe was sat slightly away from the table angled in to the room to let Pete past. as he did so Joe grabbed Sissy’s hand and jerked her forward flipping her over his knee, he took hold of her arms and held them behind her back. He said right young lady, as your so fond of flashing your knickers lets have a proper look at them, then before she could object he grabbed the skirt and gave a strong tug, the press studs all popped open and her skirt fell open exposing her glorious, knicker clad butt fully. Pete, George and myself moved round so we could watch, all three of us adjusting our trousers.
Joe said now then young lady as you were warned about being cheeky to us ‘wise old monkeys’ and teasing us relentlessly it’s time to give you your just desserts. With that Joe laid 3 good slaps across Sissy’s butt, as she wriggled, her knickers started to ride up her butt crack so Joe then grabbed to top of the knickers and gave them a tug upwards forcing them fully into her crack, showing off her, now red cheeks. Pete made a comment that her tan was not an all over one.
Joe looked at me and said 3 slaps from each of us then is it, I nodded my agreement, Pete, George and myself then spanked her. By the last slap Sissy had stopped struggling and her legs had parted showing a large damp patch on her knickers, her butt was glowing bright red. Sissy called us a load of swine, but her legs had opened a good 3 inches. Joe told her she could stand up now.
Sissy stood there looking fantastic, her nipples standing out like tent pegs poking through the boob tube, leaving not a lot to the imagination, the front of her knickers and the top of her legs were wet. Her knickers cut a nice camel toe. Sissy didn’t move, just looked at us shaking her head and said your like a bunch of bloody school kids, have you all had a good look?
George said turn round babe so we can see all of you, as she slowly turned around Pete asked if her nipples were for real, so Sissy put her hands on her boobs gave then a squeeze making her nipples standout even more, then she very slowly pulled her boob tube down to her waist, exposing totally her gorgeous tits.
Sissy stayed like that for a few minutes, then came and stood next to me with her back to the lads and looked a question at me, in answer I leaned forward taking hold of her boob tube and knickers slid them down her legs so she could step out of them. Totally naked except for her boots, she turned and faced the lads. All three of them sat, mouth agog, staring at her, her muff was well trimmed and her pussy lips were swollen heavily, her clit just visible, nipples still extended.
At that point the landlord shout last orders so Sissy retrieved her clothes and put her skirt and boob tube on and gave me her knickers. We all finished our drinks and went home.
As we approached the centre the guys all gave Sissy a hug and had a quick grope of her butt and went off. As we got to our house Sissy grabbed me dragging me behind a hedge, pulling my trousers down and mounted me wrapping her legs round my back, she orgasmed almost immediately. I carried her in to the house, taking my time made love to her lifting her to another orgasm, before I shot what seemed like a gallon of jizz into her sweet, tight pussy.
The next morning the door bell rang and Sissy went to answer it, she came back into the kitchen with a huge bunch of flowers, a note attached said “Thanks from the 3 wise old monkeys” signed by all of them.
We talked about what had happened, and how it had made her feel, she said when Joe grabbed her she had been scared and excited all at the same time, she realised that she was going to get her spanking and when we had finished slapping her she had hoped that we would start it again. She enjoyed being naked in front of them and seeing the look of total desire in their eyes made her almost have an orgasm there and then. She describe that fact that when the guys had given her a hug as we said goodnight that each of them had put their hands on her naked butt and that Joe had pushed his finger forward to just touch her pussy lips.
The talk made us horny again so we made love right there in the kitchen.
Sissy asked me where we went from here? I said it would go as far as she wanted it to go, when/if she said no more that would be it. Sissy said that as we were try to start a family and she wasn’t on the pill, she would not feel comfortable having intercourse with them as she wanted to make sure any babies would be mine.
I asked her how she felt about them touching her and if she would be willing to relieve their frustration in other ways, either by masturbating them or giving them a blow job. Sissy agreed that, that would only be fair. We also agreed that nothing was to happen in the pub again as that was too risky.
The next Friday Sissy had on the Rah-Rah skirt again with a tee-shirt. When we got there our drinks had again been brought for us. At first the conversation was a little bit awkward until I said what a great night we had, had the Friday before. Once the ice had been broken the atmosphere became comfortable and we could discuss what had happened. Sissy laid out her conditions to anything else that could, would or might happen and if the lads didn’t agree then everything would stop now.
All of them agreed to the conditions and added one of their own, that was if Sissy wasn’t comfortable/happy with what was happening she was to say – stop this is not going to happen – and the boys would then know she was serious about stopping. Sissy thought that was a great idea, she also added that it was all right with the dancing and such in the pub but if anyone else came in nothing was to happen and that she would not get naked in the pub again.
Sissy asked the boys how often they were allowed to escape from the residential home. George said that they could come and go as they pleased. Sissy then said how about we arrange an evening when you can come to us for a meal, if you all like curries I’ll talk sweetly to Paul and get him to cook one for us.
The meal was arranged for the following Wednesday evening, I had prepared a light Katso Chicken Curry with Jasmine Egg Fried Rice, we also got in cans of beer, wine and spirits. Sissy was dressed in the leather skirt and boob tube with her boots on.
When the lads arrived we had a drink and a natter to get the night rolling, then sat at the table for the meal. Sissy told me to sit with the lads and that she would serve.
When she came in even I was stunned. Sissy had, without me knowing, purchased a French Maid Outfit. The dress was black and started just below her boobs in a basque style, went down to her waist where it flaired out in a ruff and was about 5 inches long, she had on a pair of white frilly knickers. Her legs were clad in shear stockings held up by a black suspender belt, on her feet were a pair of black 5 inch high heels, the apron covered her from 3 inches from above the hem of the skirt all the way up to her neck covering her boobs so they were only visible from the side.
We all stood up and applauded Sissy in appreciation, she placed some stuff on the table gave us a little twirl gave a little curtsy, then went to fetch the rest of the food.
As we sat eating Sissy would deliberately stretch across or turn slightly exposing one of her nipples to us or leaning forward so we could see down behind the apron. After half an hour she said that it was no good her nipples were becoming sore rubbing against the apron in her excited state and asked if we would object if she took the apron off. Strangely no one objected.
Sissy slowly lifted her arms and undid the top of the apron letting it fall down, but left her hands up behind her head, sitting there now topless. The areola around her nipples had almost disappeared and her nipples were huge.
The meal finished and I cleared away all the dishes, Sissy sat talking with the lads until I came back in. Joe asked if it was alright to touch Sissy’s breast. Sissy leant forward to allow him to, holding her nipple he gave a squeeze and Sissy moaned deeply, Pete reached out and started to play with the other nipple, Sissy shuddered and seemed to have a small organism.
We all went through in to the living room, where Sissy sat between Pete and George, they continued to play with her nipples, George becoming daring, sucked a nipple into his mouth, Sissy orgasmed her whole body shaking with the force of it.
While Sissy was still in the throws of the orgasm, I lifted her up from the waist and told Joe to remove her knickers. When he had them off we saw that Sissy had also shaved all her pubic hair, Joe pushed her legs open knelt down and pushed his tongue between her pussy lips licking like there was no tomorrow. Sissy’s orgasm seemed to blow her even higher, Joe had her cum juice running down his chin and neck.
I replaced Joe between her legs and started to play with her Clitoris, it was so engorged I was using it like a dick masturbating her, while I was doing this Pete slid his fingers into her pussy, eventually he had his whole hand inside her, this lifted Sissy to an orgasm so hard that George had to put his hand over Sissy’s mouth to quiet her screams
We all played with, sucked, teased and tasted Sissy, at one point Joe was pushing most of his hand into her pussy, while I had worked three fingers into her anal passage, Pete and George were sucking on her tits while she had another orgasm.
Eventually Sissy begged us to stop and give her a time to cum down as she was getting sore and needed a drink.
Sissy told the lads to open their trousers and take their dicks out, then kneeling in front of each of them she proceed to give each a blow job taking several minutes to achieve satisfaction for them, every time they came close to release she would stop sucking and squeeze their balls to make it last longer, she had tried, unsuccessfully, to swallow all of their cum and by the time she finished she was covered in jizz, it was splattered over her face, her boobs, the remains of what she was still wearing, even down her legs.
When Sissy had finished all 3 sat there looking like the cats that had gotten the cream, Pete asked if she would let them see her totally naked again before they went home so Sissy undid the dress and let it fall to the floor standing there naked except for the stockings and suspender belt.
Her pussy lips were swollen and bright red, her nipples although still hard had reduced in size. Joe asked her to turn round and bend over. Sissy turned and keeping her legs straight, placed her feet shoulder width, bent over putting her head on the seat of the settee. The view was amazing, her pussy lips, like I said were swollen, her clitoris hung down below her lips, cum juice sparkled all down her legs.
To my surprise Sissy then slipped her hand between her legs and slowly dipped her fingers into her pussy.
Sissy stopped short of giving herself an orgasm, pulled her fingers out, stood up and turned to face us. Looking at us all she said thank you for tonight and for honouring the agreement not to have intercourse. Now I think it’s time for you boys to go home so I can rape my husband.
After they had gone Sissy said our turn now but you’ll have to wait a few minutes while I go to the loo. When she came back Sissy had taken off the stocking and suspenders and had a small box with her. She asked me to strip off and sit on the edge of the sofa, this I did.
Sissy opened the box and took out a latex double ended dildo which she covered with KY gel and pushed one end in to my anus, this felt very uncomfortable at first, but Sissy was gentle and allowed it to go in slowly, while nudging it in she also played with my prick, massaging it and playing with my balls,
When it was as she wanted it, she stepped over me and squatted down and slipped the other end into her own anus, then guided my prick into her pussy, pushing herself down so that both the dildo and my prick were embedded deep inside her.
Sissy started to rock back and forth going harder and harder as she did so until eventually she was almost lifting herself off and then slamming herself back down. At some point in this I came harder than I have ever orgasmed before, my whole body shaking and bucking underneath her.
Sissy finally let out a long drawn out mixed moan and muffled scream and flooded me with love juice, fell forward putting her head on my chest and lay there panting for ages, falling at last to sleep.
Eventually I managed to get Sissy off me and carried her to bed still asleep. The next morning I let her sleep in, taking her breakfast when she finally woke up. She said that she enjoyed the night but that she was very sore and thought it might be a couple of months before we could make love again, laughed at the look on my face, then said maybe tomorrow and kissed me.
I admitted to her that my butt was sore as well but the sensation the dildo had caused was beyond anything I had ever experienced before.
She giggled and said that when she had purchased the Maids outfit the assistant had talked to her and made some suggestions for experimenting and had showed her a collection of sex toys and explained what they did.
The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me.
Sissy punched me when I asked what type of sexual hussy I was married to.
Six weeks later Sissy told me she was pregnant. We had a little girl who had three extra Grandfathers.
Thank you for reading and I hope you enjoyed the story. If you did please let me know through the comments section.
