13/08/2020
While in college, I used to live with divorced middle aged lady, named Gabriella. She had 2 best friends, named Stella and Daniela. All 3 had different characteristics that made them sexy in my eyes. Gabriela had 36D cup breasts and very soft skin, though she was a bit chubby. Daniela had 36C breasts, was slightly darker in color than Gabriela, but had kept herself fit, with a tight tummy and beautiful, long legs. Stella was somewhere in the middle, with 34B breasts and a tummy that was less than Gabriela's, but slightly more than Daniela's. All 3 were aged between 50-55 years. I had once seen Gabriela naked when I accidentally walked in while she was taking a shower, so I know that she has beautiful looking breasts and a tasty pussy. The other 2 have always been fully covered in my presence, so I have no idea what they look like underneath.
The 3 of them always liked to play cards on saturday nights. Sometimes, I would sit with them and watch them play. They have asked me several times to join them but I always decline. I have never been much of a card player, so never really found the charm in it. Occasionally, they also a few drinks while playing, but again, I never joined them in it.
On that particular Saturday night, all 3 of them were already moderately drunk, when they started playing. I was free, so came and sat down with them, to watch. I understood the game they were playing, but did not join. Eventually, Stella asked me to join them, but I declined. Both, Gabriela and Daniela joined in trying to get me to play, but I held my own. In the end, exasperated, Gabriela asked me why did I never play with them. I just shrugged and, as a joke, told them that I don't play games in which there is no reward in the end. When asked, what kind of reward do you want, I told them that the loser would have to get naked in front of the rest. I meant it as a joke, but the 3 got a bit serious and their faces reddened. Gabriela casually asked me to fetch the bottle of wine she had in the fridge. On my return, it was apparent that they had been discussing something. When I set the bottle on the table, Gabriela said that they agreed with me and were willing to play for this reward, provided I played too. I was dumbstruck! They had agreed to the concept, but I had to get them to agree to the details. So, I told them that I would play only if a set of rules was agreed upon beforehand. The rules I proposed were as follows.
1) Each player will start with a equal number of clothing items, so that no one has an unfair advantage. We agreed upon 4 pieces of clothing. A shirt, a trouser and undergarments. When a player loses a game, he /she will remove one item of their choice in full view of the others.
2) A player who loses 4 times, will thus become completely naked. At this point, that player will be out of the game. However, he /she can't leave the room, nor put back on any piece of clothing. He /she will have to remain naked till a single winner is declared. The losing player will also not try to hide his / her naked body from the rest.
3) The losers are allowed to touch each other's naked bodies, though they may not necessarily have sex.
4) The last player left with at least one piece of clothing will be declared the winner. He/she will be allowed to demand anything from the 3 losers. He /she could order them to have sex with each other, or can take off their remaining clothes and have group sex with the losers, or can pick one from the losers and have sex with him /her in private.
I knew that getting them to agree to the sex part would be difficult, so I left it out for later but got them to agree to the whole thing in principle. They ask had another drink in order to fortify themselves, as they knew that at least 2 of them will be getting naked in front of the rest. Daniela was wearing a jacket and stockings, so we made her take those off before the game began. I knew I had been watching them play, but was not an expert in it, but had no qualms in getting naked before them, since I knew that I would see at least 2 of them naked as well.
The game started and proceeded according to plan. Every time someone lost, they would get up and take a piece of clothing off. Since the game was not a long one, pretty soon we had all lost at least twice. I was reduced to just my underwear. Gabriela and Stella were topless, sitting in just their panties, while Daniela still had her undergarments on. As I expected, seated next to the voluptuous Gabriela, Stella's breasts looked tiny! They were barely a B cup and had really large nipples. I would look at them occasionally during the game, and think what a waste. Stella, however, thought I was looking at her in lust. She would smile and wink at me, and even offered to let me suck them, but the others stopped her. Shortly thereafter, Stella lost her final game. At this, she stood up, backed away from the table, and looking me straight in the eye, smiled and slowly removed her panties to show me her pussy, with very short brown hair. Her pussy looked delicious, so I thought that this was not a total waste. Then, she sat down on the large sofa, facing the table, and completely opened her legs to give me a full view of her vagina. All she said was "Hurry up, I'm waiting for you!"
Of course, this completely distracted me, but still I managed to pull through and win the next round. Gabriela, however, lost. Unlike Stella though, she calmly took off her panties and sat down next to her. Stella put her hand on Gabriela's thigh as if to console her, but her motives soon became apparent when she tried to move her hand into Gabriela's pussy, to which Gabriela did not agree. Stella simply shrugged and started to masturbate while stroking Gabriela's thigh. Eventually, Gabriela also got aroused a bit and allowed Stella to massage her pussy. Now, the match was between me and Daniela. Her breasts looked gorgeous, even trapped behind her bra and I was determined to free them. With some difficulty, I won the next match and watched Daniela take off her bra. Her breasts did not disappoint. They were a perfect D cup, with perfectly sized nipples. I got even more determined now to have a look at her pussy. However at the very last minute, she surprised me, and won. I could not be more disappointed! I would not be able to see that lovely pussy! Oh well, I would just have to make do with the other 2 pussies sitting on the sofa. I knew that Gabriela, being my landlady, would not want to have sex with me, but Stella looked hungry for a good fucking. So, while getting up, I decided that I would start with the eager one and let her rope in the other two.
I calmly got up, walked up to the sofa, with my back towards Daniela, took one hand each of the two ladies and placed it on my waistband. I simply said "You will have to take it off yourself". Gabriela seemed reluctant but Stella was eager and forced Gabriela to comply. My 6 inch cock was already erect and quickly popped out. Gabriela looked embarrassed but did not take her eyes off of it, but Stella appeared entranced by it. She just stared at it for a minute, then slowly held it in her hand and started stroking it. Upon seeing a drop of semen at the tip, she hesitantly stuck her tongue out and licked it. Then, she just took it in her mouth and started sucking my penis. Gabriela laughed nervously at this, and Daniela started to say that she had not seen it yet, but Stella just shooed them away and continued sucking it. I absolutely loved the feel of her mouth and tongue on my cock. I even started to thrust after a while, fucking her in her mouth. After a short while, I came in her mouth and she swallowed up every last drop of my cum, even sucking harder to get every last drop out.
After this, I sat down between the ladies had them all stare at my flaccid cock. I, then, asked Daniela that, since she was the winner, what reward did she want? She just smiled and said that she just wanted to watch the three of us have sex! I really wanted to fuck her, but the rules did not allow. As I had assumed, Gabriela was reluctant to continue. She would not allow me to kiss and squirmed when I tried to masturbate her. We gave her more wine to drink and were able to convince her that if she did not want me to touch her, she could lick Stella's pussy instead. She reluctantly agreed to this and bend down to do it. I watched her give Stella oral sex for a minute then walked over behind and gently inserted my cock into her vagina. Gabriela started to object but both Stella and Daniela reminded her that she had agreed to the rules of the game before starting. At this, Gabriela agreed, and pretty soon, she was moaning with pleasure, just like Stella, as I fucked her doggy style. Since I had cum only a short while ago, I was able to fuck for a long time before cuming into her vagina. However, I did make sure that she had made Stella orgasm before I came. Even after cuming, I continued to fuck her till I felt her vagina pulsating. Only then did I reluctantly remove my cock from her pussy.
With the three of us satisfied, we now looked expectantly towards Daniela. Of course, she surprised us by getting up and gathering her clothes. She said that it was a great evening and now it was time to go home. The three of us would not have it. I quietly stepped behind her as she was trying to clip her bra and started to kiss her neck and earlobes. As she slowed a bit, I gently ran my hands into her bra and started to massage her breasts. She tried to stop me but soon was only putting up a token defense. While kissing her neck, I winked at Stella, who slowly got up and crawled over to Daniela. Then she gently started to remove her panties. The opposition by Daniela was greater this time but I was able to stop her by making her realize forcefully that she was going to get fucked either way, so she might as well enjoy it. This weakened her resolve a bit, while the rest crumbled as soon as Stella's tongue found its way to her clit. We continued like this for a while until all opposition from her had vanished. Then, having removed her bra and panties, we sat her down on the sofa, with the other ladies in either side. They opened her legs for me and I proceeded to bury my face in her crotch. The ladies, in the mean time, started to suck each of her breasts. The moaning sounds from Daniela were intoxicating, and we continued pleasuring her for quite some time, but stopped before she could orgasm.
Rather than fucking her in an uncomfortable position, I wanted to really enjoy have sex with her. Therefore, I stood her up, took her in my arms and carried her to my bedroom, where I gently laid her on my bed. Lying beside her, I started by simply enjoying her body. I kissed her from her top to bottom, starting from her lips, then chin, neck, breasts, tummy, belly button, pussy, thighs, knees, legs, and ending by kissing each of her toes. Then I started back up, until I reached her pussy. Her juices were flowing freely by then and the slight taste I got while kissing it told me that they were delicious. Thus, I started to kiss her pussy more fervently, and stuck my tongue out to play with her clit. She must have been enjoying it because her legs started to move apart, allowing me better access to her vagina. I obliged by sticking my tongue deep into her and activating her G-spot. Her moaning increased and she started thrusting her pelvis, as if helping me fuck her with my tongue. We carried on like this for a while, then I gradually slide up, kissing her naked body as I went. With my penis positioned on top of her pussy, I asked her if she was OK with this. Daniela just smiled, guided my cock into her vagina and whispered "Fuck me!" into my ear. That is all I wanted to hear. I gently slide into her and started moving back & forth. Her "Ohhh" & "Ahhh" were music to my ears. We continued like this for a long time, gradually picking up the pace as she neared her orgasm. Eventually, my pace and energy reached such a crescendo that the bed started squeaking and banging against the wall, promoting Stella & Gabriela to peek in to see what was going on. The sight that beheld them made them come in, sit on the floor and start fingering themselves. Daniela's gentle moaning has also increased to actual screams of pleasure, with "OH YES! FUCK ME! FUCK ME HARDER! I'M COMING! FUCK MY PUSSY HARDER!" Of course, I obliged by thrusting into her and grinding her pelvis as if it was the last pussy I would ever get to fuck. Pretty soon, her screams changed to "IN COMING! OH GOD , I'M COMING!" I continued but was on the verge myself. Then, with an ear piercing cry and the arcing of her back, I knew she had orgasmed. I increased my pace to coincide with her, and emptied my load inside her vagina shortly thereafter. As we lay there, we heard a rising cry from the floor, only to see both the ladies there masturbating themselves to another orgasm.
We all just lay there, too tired to move, before Daniela started to get up. I realized my penis was still inside her, and gently took it out and let her up. The other two had also stood up, and were smiling. That smile turned into a laughter and pretty soon all of us were laughing uncontrollably. Stella was the one to stop first and said that it had been fun but they had to get back home. So, we all got up and got dressed. Stella and Daniela then left, leaving me and my landlady, Gabriella all alone. She got up and said that she was going for a shower. I asked if she needed company. She just laughed and said "No, am too tired for company". Then, just at the bathroom door, she turned and, with a mischievous smile, said "Maybe later." I just laughed and lay down on my bed, thinking how life was going to be so much more interesting from now on.