Literotic asexstories – Oliver, His Mother and Her Friends by Pussyfan69,Pussyfan69 Oliver, 20, an electrical apprentice trainee, lived at home in the suburbs with his mother, Jean. That’s it, his father hadn’t been seen for several years; last they heard he owned a girlie bar in Thailand.
Oliver came in from a college day looking and sounding grumpy.
“Not had a good day,” asked Jean.
“I had a date lined up for the weekend, first time in months. She cancelled on me, apparently she has found true love with a guy who looks like he escaped from a federal penitentiary and lives rough on the street.”
“You are good looking, well dressed, friendly – I would thought the girls would be around you like bears around a beehive,” Jean commented.
“I’m headed to die the world’s oldest, best dressed, charming virgin, do you think paying for sexual experiences would give me some kind of confidence or poise that I now lack?” he asked.
“Leave it with me, I’ll think of something.”
Later that evening Jean passed Oliver’s bedroom door which was slightly ajar. She knocked, heard a sound and entered. He was in bed, knees up to make a tent, looking at porn on his tablet.
Jean apologised for disturbing him and continued, “I’m in a bit of sexual drought period myself.”
She sat on the bed, slid a hand under the covers, and gently moved around his thighs and body, but not near his erection.
“I can give a bit of relief but as long as you realise that you are never going to get my pants off.”
Oliver said nothing, he was excited but also frozen from embarrassment and fear.
“You have any personnel body lube in here?” she asked.
Oliver pulled out a tube from under the covers.
“I have some better stuff, back in a minute or less,” Jean said as she got to her feet.
On her return she pulled the covers down and fully exposed her naked son.
“My God, that cock is magnificent. Bigger and thicker than your father’s or any I’ve seen since he left. It’s positively handsome. Have sex with one girl about your age and she will boast to all of her friends that she is acquainted with the best cock in the State and they will be after you.”
Jean lubed his cock and gave him a hand job alternating between one hand and two hands. When one hand was free she cupped his balls or fingertip tickled them.
Oliver who had his eyes closed throughout quickly finished, Jean caught the cum in her hands and left the room wash it off.
On her return she said, “I think we should have a brief break and go for another round.”
She laid down next to Oliver and hatched a plan while casually holding his cock in readiness for its recovery.
“I suggest some experienced, older ladies to take you to the next level.”
“I’ll take anyone, anywhere and do anything to lose my virgin badge, I think I emit an aura of incompetence and inexperience that might have been normal at an earlier age,” observed Oliver.
“Keep your eyes open this time, I’m going to take my top off,” Jean whispered as she took off her shirt and bra.
She started to lube up his clock but stopped suddenly.
“Fuck this, I’m going to strip off and go all the way,” pulling down her jeans and panties in one movement.
She took Oliver’s right hand and extended the forefinger putting a dab of lube on it.
“Put this in your mother’s cunt, the first cunt you have ever fingered I would guess.”
Oliver slid the finger in while Jean held open her pussy lips.
“Lesson one, outer labia, inner labia and clit. I’m sure you are familiar with this from porn videos but males have to learn the angle of penetration to get their fingers and cocks in easily. Funny how many experienced men need a hand to get it in”
Oliver was in no hurry to extract his finger but Jean pulled back.
“Male on top missionary I think for a first timer,”
Jean used a hand to guide him in, “see, it takes a bit of practice to line it up and push in the right direction but you are doing fine for a learner and your cock feels like it belongs in there.”
Oliver finished quickly with a few quick thrusts and accompanying sound effects.
“Did I cum prematurely then?” he asked.
“Not at all, first few times in you are super sensitive. You will gradually be able to control the duration.”
The following day Jean had some news, “I listed several very discreet friends who I think would love to experience your cock, meet you and give you a few tips. I decided to just go for two for now so as to leave some of your energy for me.
Emma is forty, I’m sure you will recognise her. She was widowed about two years ago. She tells me that she often sees you around the neighbourhood and you can make her pussy wet from across the street.
Suzanne is a bit younger than Emma, her husband ran off with their babysitter. You have seen her here a few times. She would be on our doorstep in in five minutes if I called her now.
Are you going to be home tomorrow night? If I get them over here for card games, the winner, between Emma and Suzanne, will be sent up to your room, the second placed will leave her address and phone number for you to call her.”
“I was going to stop on the way home for a sexy massage, I have an escort booked for seven for an hour and then I have two eighteen year old twins and their mam coming over for a foursome. But I can cancel them all.”
“Very funny, I think you should play cards with us.”
“I would prefer to be in my dimly lit room.”
“Sit at the card table, pretend to be cool, calm and unexcited, smile, check them out but not with a fixed stare. Try to get into their heads before getting in in to their pants, what motivates them, what makes them laugh, how do they react to various topics. Be interested in what they do and what they think. This is a very important part of your training.”
“Brilliant, you should teach this stuff at college or go viral on the internet.”
“On further thought, a few more points, when you get to the bedroom, casually undress – do not wait for Emma or Suzanne to take the lead. You are always respectful of others, the key here is communication, what does she want, what do you want, what works for both of you,” Jean added.
The card games were great fun, Oliver’s contribution to the conversation served him well.
The competition between Emma and Suzanne was palpable, thinking that females might be attracted to him was a tremendous boost to Oscar.
The final card game started as a draw but Emma won by a point.
Jean and Suzanne went to the TV room; Oliver took the lead and invited Emma to his room.
They had a hug and a kiss and started to undress.
“I do have a bit of an issue I would like to discuss before I pull down my panties,”
“I find this quite embarrassing,” continued Emma, “I have protruding inner labia or pussy lips if you prefer, they are not even symmetrical, I’ve considered surgery – sometimes I think they look like a ham sandwich the dog has been chewing. We can have fun in the dark if you like but I had to warn you.”
Emma had nothing left on other than shorts and panties. He stood her in front of him and sat on the bed facing her. He slowly moved the shorts and panties down and Emma stepped out of them.
He parted her legs and looked down at a bushy area shaved at the bikini line. He inner labia could certainly be seen but Oliver thought it looked very inviting. To prove the point, he dropped to his knees and plunged his tongue in. After a while he guided Emma to the bed, legs parted, knees up and he dived in again.
“Everything down there is pretty, attractive, just perfect. If I was small enough I would move in there and seldom leave,” he enthusiastically claimed.”
“While we are throwing compliments around, that cock of yours even exceeds your mother’s glowing description of it.”
“That’s the equipment all sorted,” said Oliver, “now for a test drive, do you like doggy?”
“My favourite, but I need some kissing before and after as it can’t be done while we are doing it.”
They kissed passionately while exploring each other’s body and Emma got in to doggy position.
Oliver admired the view, he stroked her pussy and then parted her butt cheeks to find a very neat looking butt hole a fine accompaniment to fucking doggy style. He was not sure if she was tighter than his mother, a different position could give different feelings. His head was spinning with similar thoughts.
He also found the prominent pussy lips a remarkable asset. On the back stroke he could sometimes completely withdraw finding pushing back through the pussy lips exquisite. Emma appreciated that part too.
“Are you staying the night,” Oliver asked almost in a pleading tone.
“You are going to need a serious team of muscle-men bouncers to get me out of here before breakfast time.”
A few days later Oliver called Suzanne and they made a date.
My parents own a cabin a one hour drive from here. Are you available Friday evening to late Sunday, It would be just us,” she offered.
A few days seemed like an eternity for both of them but they eventually arrived at the cabin.They unpacked and got organised. The main bedroom was on the mezzanine level and gave an excellent view of the lake.
“Up for a swim in the lake,” asked Suzanne, “the other cottages are quite far away and it’s getting dark so I don’t think we need to wear anything.”
“I’m up for anything involving nudity and you in the same sentence,” he replied while undressing.
When Suzanne took off her panties, Oliver stood back and admired her giving her a whistle and two thumbs up.
“Last one in the lake does dishes tomorrow,” said Suzanne knowing that Oliver would be faster but she was intimately familiar with the narrow 100 yard path to the water and would have to lead on the path anyway.
Oliver realised he had been tricked; when they got to the water he grabbed her and lifted her in to his arms. He wasn’t sure what to do next and didn’t want to risk hurting her so he just carried her in until he was waist deep.
“I guess that was a tie so we share chores,” she said, clinging on to him tightly.
They swam around a bit and then stopped and kissed for the first time.
“Can men get erections under water?” she asked.
“Never thought about it, certainly in a bathtub but in cool water finding a shrivelled cock would be the first challenge.” he observed.
“I suppose sex in a lake might not be too hygienic.”
“I’ll have to wait then,” pouting his lips.
“Not for long,” Suzanne said, grabbing a hand for the jog back to the cabin.
It had been a long day, Oliver stretched out horizontally on the rug in front of the fireplace to take a few deep breaths before the main event while Suzanne was drying her long brunette hair to her satisfaction.
Suzanne walked over and sat on the floor next to him, reaching for his cock.
“Is the little guy recovered from the cool water?”
“You bet he is.”
Suzanne held his cock, admired it from all angles, used her tongue to find the most sensitive areas and sucked it for just long enough to take it from hard to hard as granite.
She then mounted him, “cowgirl OK with you?”
“Best view in the house, I can see and touch your pussy and tits and I you can reach to kiss me whenever the mood takes you there so what could be better?”
The weekend only got better. They had to put clothes on if they hiked around the lake but didn’t need to be wear clothes around the land belonging to the cabin.
When it was time to leave, Suzanne asked Oliver what he considered to be the best part of the weekend.
He answered, “getting to know you, sex, being naked together, sex, talking together, sex, waking up next to you, sex, everything else and did I mention sex?”
Leave a Reply