Cindy's First Time

Literotic asexstories – Cindy's First Time by XXXerxes37,XXXerxes37
Gloria was talking to her daughter Cindy about why she didn’t appear to have any boyfriends. Cindy was eighteen years old and currently had no boyfriend on the scene. She had in the past had a few dates but being quite a shy girl had not experienced anything more than minor sexual pleasures.

She had started dating at the age of fifteen and it took about four dates with her first ever boyfriend Brian before she permitted him to touch her breasts whilst still wearing her sweater. She had nice pert breasts, not very large but nevertheless they gave a welcome shape to her figure. On the next date Brian had taken her out in his car and parked by the side of a deserted lake. After kissing her passionately for several minutes he then tried to move his hand under her sweater but she pushed his hand away. He tried again but she again pushed him away. On the third attempt not only did she push his hand away but said “Brian, that’s not allowed.”

And slapped his face at the same time.

“It’s time for you to take me home now.” She said witheringly. He slipped from the clinch they were in, started the motor, engaged gear and drove her home. When they arrived she got out of the car when he opened the door for her. She then said, “That’s the last time we shall be together Brian. You do not respect me enough. Goodbye!” and with that she flounced into the house, slamming the door loudly behind her.

Each subsequent date had succeeded in getting further than the previous one before being shown the door. The last one, also by coincidence a Brian, had been permitted to remove her bra and play with her breasts. He was even allowed to lick and suck her nipples. He had also been given liberty to rub her cunt over the top of her knickers but when he tried to put his hand inside that was the end of his friendship. She was just about to reach her eighteenth birthday when she dismissed him from her life.

That was six months ago and since then her reputation meant that she found it impossible to get any dates. She had come to her mother for advice.

Gloria was quite blunt with her daughter and told her, “In this day and age men want either to marry a virgin or date an experienced woman. I assume you are not yet ready to get married and so you must either remain on the shelf as far as dates go, or get yourself some experience.”

Cindy looked aghast at her mother.

“B b b u uu tttt… ” she stuttered.

“Go away and think hard about it Cindy, and when you have made any decision, let me know and I may be able to help.”

Cindy left and took a week to make her decision. She called Gloria saying, “Mother, I have decided that before I get married I want to enjoy the life of a liberated woman. Can you help me?”

“Yes,” said her mother. “Come round here next week and I will be able to help!”

So the following week Cindy went round to her mothers. Gloria sat her down on the couch, gave her a large glass of vodka and said, “Right Cindy, this is what I have decided for you. Tonight you will be shown several exciting sexual activities. After you have been shown each one you will be given the opportunity to enjoy it for yourself. You may decline any activity, but if you do the session will end immediately and you will have to find someone else to assist you in the future. Do you understand?”

Cindy reluctantly said, “Yes, I think so.”

“Good.” Said Gloria, “Finish your drink and we’ll now go upstairs to my boudoir and prepare you for your evenings pleasures.”

They ascended the stairs and entered Gloria’s boudoir.

“Stand over there and strip.” Ordered Gloria. Cindy was taken aback by this peremptory order but she did go and stand where instructed. However, Gloria had to repeat the order to strip as Cindy didn’t appear to be taking any action. For a third time Gloria, now with a load yell, bellowed “STRIP!!”

Cindy slowly took notice. First she removed her sweater, then her skirt followed by her shoes and pantyhose. She then stood before her mother dressed in only her unsexy bra and her thick cotton knickers.

“I said STRIP!” said her mother “and when I say STRIP I mean STRIP. That means everything, all you are wearing!”

Cindy reluctantly put her hands behind her back and unclipped her bra. She moved her hands to her front and when she had let the bra fall to the floor covered her pert breasts with her hands.

“I’m your mother.” Said Gloria. “I’ve seen all you have since you were born. It’s no use hiding anything from me. Besides, you have to get used to being less inhibited tonight because tonight you are going to change!”

Cindy let her hands fall to her side before moving them down to remove her knickers.

Finally she stood before her mother stark naked.

“That’s better.” Said her mother. “Now turn round slowly so I can have a good look at you.”

Cindy did as she was told. Her mother let her stand there for along time, letting her get used to being naked. Eventually she said, “Now walk round the room several times, keeping your head up at all times.”

Again Cindy did as requested.

When Gloria thought she had gone round enough she told her to stop. She got up from the chair where she had been seated all this time and approached Cindy with another glass of vodka.

“Here love, drink this down it should help.”

When Cindy had emptied the glass and placed it by the bedside her mother reached out and caressed Cindy’s left breast. Cindy immediately flinched and tried to push her mother’s hand away.

“Remember what I said before we came upstairs Cindy? This is your first and only warning. Next time you decline anything the evening ends.”

Gloria now started caressing Cindy’s right breast and with great willpower Cindy managed to restrain herself from pushing her mother away. ”

Good!” said Gloria. “You are improving.”

Next Gloria moved herself even closer to Cindy and took her left nipple into her mouth. Cindy’s immediate reaction would have been to back away rapidly but she remembered what her mother had said and managed to remain in place. She started to feel a little strange. Although she didn’t know it she was starting to become aroused. At the same time as she took the nipple into her mouth Gloria let her hand slide down towards Cindy’s cunt. Soon she was sliding through the surrounding dark hairs and before long her fingers were touching Cindy’s nether lips. Cindy had never felt anything like this before. She had never in her eighteen years even felt her own lips!

The fingers now slid inside the lips and began caressing the entrance to her cunt. They could not go too far, as Cindy was still a virgin. Gloria removed her fingers and lips and stood back.

“There,” she said, “That’s your first lesson tonight and you have done quite well.

Now it is time to get you ready for the main entertainment. Come over here to the closet.”

Gloria now opened the closet and began removing the articles of clothing she had determined that Cindy should wear for tonight. First a slim sexy garter belt which she handed to Cindy.

“What’s this?” said Cindy, never having seen one before.

“That is a garter belt.” Said her mother and proceeded to show Cindy where and how it was to be worn. Next came a pair of black stockings that Gloria assisted Cindy to put on and fasten to the belt. The next item was a pair of black and red crotchless panties that quickly found themselves round Cindy’s waist, revealing most of her hairy cunt of course. To finish the underwear Gloria produced a front fastening, skimpy, lacy black bra. When Cindy had donned this she was now ready for the final external trimmings. First a loose fitting see-through white nylon top followed by a wide swirling skirt which didn’t even reach the knee. Six-inch heels followed and now Cindy was clothed, only needing her makeup to be fixed before the evening really started. When her make had been completed the two women went back downstairs to await the developments.

Cindy was given another glass of vodka and had only just emptied the glass when the doorbell rang and Gloria went to the door to let the visitor in. It was a young man, good looking, about 6ft and well made. Gloria ushered him through into the lounge where Cindy waited with anticipation as to who it might be. She immediately saw that it wasn’t her father so she said to Gloria, “Who the hell is this, mother?”

Gloria replied, “As your father spends most of his working life away from home I have to have an outlet for my sex drive. This is it. His name is Gordon, he is a very good lover as you will find out in due course.”

Gloria then took Gordon’s jacket and hung it on the coatstand. She then invited him to come over to the couch where Cindy was seated. When he was facing Cindy and close enough to touch, Gloria moved to his side. She enclosed him in a long embrace, giving him a series of ‘welcome to my home’ kisses before releasing him. She now moved her hand down from touching his lips until she reached the zipper on his jeans. Having reached it she now proceeded to drag it down to its extremity, allowing his rapidly growing cock to emerge as he wore no underwear.(As previously arranged with Gloria.)

Gloria now took Gordon’s cock in her hand and began to stroke it lovingly. When she was satisfied it had reached its full potential she gave it two more strokes and said to Cindy, “Now its your turn. Take it in your hand and stroke it for him,”

Cindy was about to protest that she had never held a mans cock before when she remembered the conditions. So she tentatively put out her hand to stroke it. Gloria said “No, not like that. Hold it nice and firmly with your hand wrapped round it. Then wank it up and down a couple of times.”

Cindy gingerly wrapped her hand around it and did as her mother had instructed. She then released it as fast as she could.

Now Gloria knelt at Gordon’s feet and took his cock into her mouth, slowly swallowing most of it but not allowing it into her throat. That would be too much to ask of Cindy at this stage. She sucked it in and out several times giving it a good coating of saliva before allowing it to slide out completely.

“Your turn Cindy.” She said getting up off her knees.

Cindy reluctantly got up off the couch and slowly knelt down before Gordon. She moved her mouth towards his rampant cock and gave it a little lick with her tongue, looking towards her mother as she did so. Her mother indicated what to do next so she slowly let the end into her open mouth. She was now able to taste the mixture of pre-cum and her mother’s saliva. It wasn’t as unpleasant as she thought it might have been so she moved it a little further into her mouth. Soon she had as much as she could take without gagging and was beginning to feel quite excited as she began to slide it in and out of her mouth.

“Keep going.” Said Gordon and her mother simultaneously. She continued until Gordon indicated that he was too close to cumming and made her pull it out of her mouth.

“Very well done.” Chortled her mother.

“You looked as though you almost enjoyed that.”

“I did.” Replied Cindy, going back to the couch.

The next lesson required Gloria to move over to the couch alongside Cindy. Before settling on the couch she unzipped and removed her skirt followed by her panties.

Cindy gave an involuntary shudder as she saw her mother’s naked cunt revealed to her eyes for the first time. Gloria perched on the edge of the couch with her wide-open legs hanging very well forward. Gordon removed his jeans and knelt before Gloria, bringing his erect cock close to her waiting cunt. Gloria told Cindy to look closely at what was about to happen next. As Cindy watched with baited breath she saw Gordon’s cock move into her mother’s cunt. First the tip disappeared and then the rest was slowly swallowed up by her mother’s cunt. Gordon now started his in and out movements and Cindy was able to see the cock appear and disappear before her. After several in and outs Gloria said to Cindy, “Let him see your tits Cindy.”

Cindy pushed up her transparent top and held it above her tit filled bra. Gordon reached over and undid the bra’s fastening allowing the bra to fall open revealing Cindy’s lovely little titties.

“They are lovely,” said Gordon moving his hands to cup and caress them whilst still pounding into Gloria’s lubricated cunt. Having given them a good working over with his hands he now leant forward and took her right nipple into his mouth. Cindy felt feelings she had never in her whole life felt before. She didn’t know it but she was rapidly approaching the first ever orgasm of her life!

“Take your top off!” demanded Gordon and Cindy raised her arms and took the top off over her head. Gordon continued his dual role of rousing Cindy and fucking Gloria. They were all approaching the point of no return when Gloria decided it was too soon so she signalled to Gordon to cease activities. Gordon pulled out of Gloria and Cindy could see his cock emerging from her mother’s cunt all covered in Gloria’s juices.

“Get back on your knees Cindy!” ordered her mother.

“Take Gordon’s cock back into your mouth,” she continued. Cindy hesitated only slightly before taking the slippery cock back into her mouth and proceeded to slurp up the juices with more vigour than the last time. Before Gordon reached climax he pushed Cindy away again.

“Now Cindy,” said her mother.

“Now it is time for you to lose your virginity. Gordon is going to push his cock into your cunt and break your hymen. So take off your skirt and lie on the sofa with your legs wide open. As your panties are crotchless you can leave them on.”

Cindy did as she was told. She removed her skirt and lay down on the couch with legs wide open.

Gordon now moved over to the couch and crouched over Cindy, first allowing her to take his cock into her mouth for a quick slurp before moving down her body until his cock rested in the abundant hairs just above her cunt. He took his hand to her cunt lips and parted them with his fingers. He was pleased to find she was very moist. The preliminary actions had aroused her, causing the lubrication to her cunt. He moved his hand and slid his cock down until the tip opened her lips. He began to slide very slowly into her until he came to her hymen whereupon he stopped and said “This next bit might hurt, Cindy, but the pain should soon go. So hold tight. Here we go!”

With that he withdrew his cock slightly before thrusting as hard as he could into her virgin cunt.

“OW!!” yelled Cindy as the cock broke through and took her virginity. Gordon now began a gentle in and out motion and soon Cindy was feeling good again.

Her mother moved over to the couch and gave her a kiss before moving her mouth down to nibble at Cindy’s nipples, complementing Gordon’s thrusting into her cunt. Suddenly Cindy felt very strange. It was a very pleasant strange, in fact she was having her very first orgasm.

“Ohhhhhhhhhh……” Escaped from her lips as she went over the edge. Gordon speeded up his strokes and Cindy experienced her second climax soon after.

When she had recovered Gloria moved from her nipples and stood up. She asked Gordon to slide out of Cindy so she could have a taste of her daughter. Gordon obliged and Gloria could see his cock was covered in a mixture of Cindy’s juices tinged with a few spots of her hymenal blood. While she continued sucking Gordon’s cock Gordon moved over to Cindy and started to tongue her open cunt, paying particular attention to her clit.

Cindy didn’t know what was happening to her as she convulsed with her third orgasm in quick succession.

Gloria released Gordon’s cock and he again inserted it into Cindy’s gaping cunt. He quickly increased his pace and as Cindy hit her fourth orgasm he stiffened and with a great roar spewed all his pent up sperm deep into Cindy’s unprotected cunt. They lay unmoving for several seconds before Gordon’s cock began to lose its stiffness and slide out of Cindy’s filled cunt. They now lay side by side for several minutes, savouring the pleasures that they had just enjoyed together. Eventually they recovered and rose up from the couch.

Gloria came over to her daughter and they embraced and exchanged several meaningful kisses.

“There now Cindy, you are now a changed woman and can go out into the world and enjoy yourself.

“Before you go Gordon,” said Gloria “I would like you to fuck me. Cindy has had most of the fun and I haven’t had a single orgasm yet.”

So Cindy took up her position with legs apart and stretching out from the front of the couch. Gloria took up a position on all fours with her face between Cindy’s legs. She not only wanted to be fucked in the doggy position but she also wanted to suck Cindy’s creampie. As Gloria put her mouth to Cindy’s violated cunt Gordon moved up behind her and inserted his now revitalised cock into Gloria’s cunt.

What lovely feelings for all three. Gloria was being fucked in her favourite position, Cindy was receiving a good cunt sucking and Gordon had his cock in its favourite place – A woman’s cunt. The climax of the evening was when Gordon filled Gloria’s cunt with his hot sperm after she had had two orgasms and Cindy had also been brought to yet another orgasm by her mother Gloria.

The evening had been a great success, Cindy had lost her virginity and all had been sexually satisfied.

Follow up to Cindy’s losing her virginity.

Cindy was not able to enjoy a full sexually liberated life for long because when Gordon had taken her virginity and cum deep into her cunt she had become pregnant. She didn’t find out immediately of course and in fact had a few more sessions with her mother and Gordon, learning to suck her mothers creampie and also the art of deep throat.

When she did eventually give birth her mother adopted the child and Cindy began her new life.

I may write about her new life if I get enough encouragement.