Brian needs sexual experience. But he can always turn to his mom.
Brian was a nerd. A fully paid up, card-carrying, book-reading, gaming, sci-fi watching nerd. He was in his last year at high school and had never had a girlfriend. His mom, Rose, had considered he may be gay until she found some very straight porn under his bed. He had just shown no interest in girls. He was good looking and kept himself in shape. He wasn’t athletic in any way but slim and well-groomed. It was the grooming bit that was one of the reasons Rose thought he may be gay.
Rose was probably the best looking forty year old most guys had ever seen. Around 5’5”, slim with large natural boobs and long brunette hair. She kept her skin and nails immaculate and wore a sensible amount of make-up, unless going out, then full war paint. She was an office manager in charge of lots of men and women so did not lack in self-confidence. During the day she was dressed in perfectly co-ordinated business attire and at night in stunning short, low-cut dresses. But she could dress down too and generally wore very casual clothes when at home with Brian. She was a different character when she was with him. At work she was efficient and strong. When she was out with the girls, or men, she was fun and flirty and could hold her drink. But at home with just Brian, she was kind and sweet and very attentive. He was her little boy and she had raised him single handed since she kicked his father out sixteen years ago. She also had not really had a full on relationship with a guy because of wanting to look after Brian. She imagined once he had disappeared off to college then she could find someone to settle down with perhaps. But don’t imagine that stopped her from dating. She was attractive and confident and along with that she was sexually aggressive. Not in a dominant kind of way but she knew what she wanted, what satisfied her and she took exactly what she needed from a man. Then more often than not, moved him on.
Brian was aware of her sexual proclivities. More than once had he heard his mom described as a MILF. It was a not a term he liked but he had heard other words too and mostly from boys at school. Although he knew she wouldn’t entertain boys like them. She wanted someone who was mature and didn’t need looking after. She had Brian for that. She never brought guys home when Brian was there. Sometimes they could come by to pick her up but never stayed overnight. She was careful that way. She really thought that Brian didn’t see that side of her. Or at least she hoped he didn’t. But he had watched her come and go with guys since he was young. Heard gossip about her. Saw her dressed to kill on her nights out. But it went further than that. He would often take a longer than necessary look at her cleavage or watch from behind as she walked up the stairs. He had ‘accidentally’ walked in on her getting dressed several times. And often, whenever possible, had snooped through her lingerie draw and even sniffed her used clothes in the laundry basket. Just the smell of her perfume, mixed with men’s cologne, set his imagination running wild. He wasn’t proud of the fact but he was just a teenage boy after all.
It was one Friday, when Brian was in his room doing whatever Brian did, and Rose was getting ready to go out on a ‘date’, that he received a visitor. The doorbell rang a couple of times and Rose was forced to answer it as Brian had his headphones on. It was a young girl. Brian’s age or just a little younger. Blonde and extremely pretty. Rose smiled as the girl announced who she was.“Hi. I’m Kayleigh. I’m sure Brian’s told you about me. Is he home?” Rose had never heard of this girl. But she wasn’t letting the cat out of the bag. “Oh sure. Do come in. I’ll call him.” She showed the young girl into the lounge and went upstairs to find her son. She entered his room. She was excited that Brian might have a girlfriend and not told her. “Brian,” she called pulling his headphones off. He was startled. “Kayleigh is here to see you. Who’s Kayleigh?” Brian squirmed and went crimson.
“Tell her I’m not in. I can’t see her now.”
“But I’ve already told her you’re home.”
“Mom. Please. Not right now.” She reluctantly agreed.
“Ok. But you have some explaining to do.” She returned downstairs and made an excuse about him being in the shower and some other nonsense. Kayleigh left disappointed. Rose checked her watch. She was running late and hated being late. She finished up getting ready and said goodbye to Brian.
“I won’t be late tonight. We can have a chat when I get home.” Rose kissed him on the cheek and left a slight red stain with her lipstick. It was a bright red colour and matched her stunning dress. A Gucci number showing off her body shape, her lovely tits and divine legs. Her expensive red heels set the whole outfit off. “I’m intrigued to know about Kayleigh.” Brian pouted and she left.
Rose was good to her word and back home by ten thirty. She poured herself a large glass of Chablis from the bottle in the fridge and clipped up the wooden stairs towards Brian’s room. Her night had been just short of a disaster. It was dinner with a professor from a local college whom she had met on a dating site. It was an optimistic thought that by choosing an older gentleman with a good education and respected profession that her date wouldn’t spend the night staring at her breasts. But she was wrong. There were certainly nights that she wanted nothing more than a good fuck from someone her age or younger, even if they were dumb as mud, but this wasn’t one of them. A wasted night watching an old man drool and having to drink a whole bottle of house red to herself because her date thought it might interfere with his blue pill. So she sent him home to interfere with himself. Another large glass of wine might just take the edge off. She stumbled slightly as she pushed open Brian’s door with her backside, desperate not to spill any alcohol.
Brian was lying on his bed watching some movie with aliens. Rose pulled up a chair, positioned it by his bed, sat down and removed the tv remote from his hand. She hit the off button and the screen went black.
“So, Hayley?” She started. He could smell her breath and it was clear she had been drinking but she was certainly not drunk. “What’s the story with her?”
“You mean Kayleigh.”
“Yes I do. What a nice girl.”
“There is no story with Kayleigh. We’re friends. We belong to a role playing group at school. Our characters are a couple and she wants to take it into real life. But I’m not ready.” Rose took a sip of her drink. More of a gulp really.
“Why not ready sweetie? She’s very pretty. And she clearly likes you.”
“That’s the problem. She does like me. And then if I start seeing her then she will want to hang out. Eventually she will want us to be physical. And that’s what I’m not ready for.” Rose took another gulp. She guessed he was still a virgin.
“How come sweetie? Do you think you’re not old enough? We all have to start some time.”
“It’s not about age.” He hesitated. “I have a small cock and I’m know I’m going to be a big disappointment.”
Rose lifted her glass to take another gulp but there was barely any left. She drained the glass and put it on his night stand. She was playing for time. She had to be careful with her answer here. Rose had not really seen his cock for a few years so had no idea what size it was. And apart from size, sex was a confidence thing. She had to reassure him.
“Don’t think size is everything sweetie. And if you haven’t done anything how do you know you won’t be good? She may be in the same situation.” He frowned. He was going to take a lot of convincing. “Let me have a look?” She suggested.
“Huh? I don’t think so,” was his instant reaction. Rose said nothing but smiled lovingly at him. He started thinking. It was a very odd situation he was in. Showing his mom his cock? That’s not normal. But she had seen it before. Not recently but at some stage. And she was not likely to judge him. If he couldn’t show it to her then how could he get the courage to let Kayleigh see it? He was making a good argument.
They sat in silence for a few moments, Brian desperately avoiding eye contact. Then, after a big sigh, he tugged down his sweatpants and let his genitals all hang out. Rose looked down nonchalant. She had seen small ones before and knew that you don’t show surprise. It was certainly on the small side but not tiny. Maybe three or four inches. Rose had seen smaller and had been fucked by them. If he knows how to use it, this could work. His cock was lying across his balls, a little curled up and between his legs. Rose reached out and raised it up between two fingers so she could get a better look. Brian looked horrified.
“Yes,” she said. “That’s workable. How stiff does it get?” She began slowly working it with her hand in an attempt to get an erection. Brian turned bright red. He wanted her to stop her but he chose not too for two reasons. Firstly was that it was his mom. She always knew best and was clearly trying to look out for him. Secondly because he was enjoying it too much. Rose knew what she was doing and had him stiff in a matter of seconds. His cock grew by an inch or too, still not large, but became incredibly hard. That was a good thing at least. Rose licked her lips and winked at him. A bit inappropriate perhaps but she was almost on auto-pilot. She had a firm grasp of his shaft and run her hands and down a few times. A few times was all he needed as his white sticky liquid erupted from the head of his cock. Rose, if she had been expecting it, would have wanked every last drop from him but because of her surprise reacted badly by pulling her hand away. From her having him stiff until him ejaculating had been around thirty seconds. Both unexpected and unfortunate.
Brian groaned and pulled his sweatpants up immediately to cover his embarassment.
“Darling, let me clean it off first,” she said and reaching for he tissues conveniently places by the side of the bed.
“NO. You’ve done enough.” Brian was terse. And majorly horrified. Now his mother knew his problem. He would just remain a virgin for the rest of his life. That’s that.
“Brian. Don’t be silly. This is normal. Really it is.” That was partially a lie. It was true that this was the first time a woman had seen his adult cock and that she touched it and played with would have been overstimulating for him. He had no experience to judge that by. But Rose knew that by definition, that was premature. Her only hope was that in future he could curb his excitement and have more control. It was hope more than expectation.
“Go away.” He commanded. He didn’t like speaking to his mother like that. He turned at looked at her. “Please?” He asked in a softer tone. She knew he needed to be alone with his thoughts for a while so she grabbed her empty glass and left.
Brian was indeed left alone with his thoughts and what a mixed bunch they were. He imagined he would be more upset than he was. Mostly he was excited and turned on. Which then made him disgusted. But didn’t stop him thinking about the moment he came over his mom’s hand. As that image recurred to him, he heard the clippety noise of Rose’s heels on the stairs. No doubt having refilled her glass. He pondered for a while before getting off the bed and heading for the bathroom to clean off his cock. Something he was well used to doing. He removed his sweatpants and exchanged them some Calvin Klein underpants, spritzed himself with some cologne and combed his hair. He padded nervously down the hallway and found himself outside Rose’s bedroom door. He felt as though he should knock but he had never done that before, he normally just went in. The door was slightly ajar so he peered through the crack. Rose was sitting at her dressing table taking off her make up. When she had done so, she slipped off her shoes and stood up. Brian chose this time to enter.
“Oh hello sweetie.” She seemed pleased to see him. And not surprised he was in his underpants. He often walked around the house like that. “Just in time. Can you help me with my dress?” She turned her back to him and pointed vaguely towards her zip. Brian slowly lowered the zip down her back until the top of her panties were visible. Red lace things they were. She slipped the dress off her shoulders and stepping out of it, took it towards her walk-in closet and hung it back in it’s place. She re-merged now only clothed in red underwear. The bra was as lacy as the panties and was barely holding in her ample breasts. She looked like a forty-something underwear model.
“You ok Brian?” She prompted, taking his hand in hers.
“Yes. I will be. I’m sorry about before.” He was interrupted by Rose placing her finger on his lips.
“Shush. No need for sorry. I just want to help.” She hesitated. “We can practice if you like. Things will get better. If you can learn control. Really it will.” They exchanged smiles. Rose reached into her drawer and removing a skimpy silky nighty, covered herself up a tiny bit more.
She sat on the edge of her bed.
“Come lie down,” she invited, patting the bed firmly. He was keen to do so. Flat on his back, hands behind his head, looking up at his mom. Rose leaned over him and kissed him softly on the lips. She whispered softly in his ear. “I’m going to make this good for you. I’ll teach you everything you need to know. Trust me.” He looked her directly in the eye as she leaned in and kissed him again. Not a mom kiss. A quite erotic soft, wet kiss. He responded as best he knew how.
“Not too firm,” she instructed him. “Softer and try using your tongue a little.” They French kissed like lovers. Rose reached down to his Calvin Kleins and grabbed at his firm bulge. He lifted his bum as she slipped the underpants away and revealed his rock hard cock. She was impressed that he got wood again so quickly and she started to stroke it gently. Only a few strokes and then she paused. She didn’t want it going off in her hand again. She ran her hand over his chest, kissed him softly and stroked his cock again.
“How’s that?” She asked.
“Amazing. Fucking amazing”. He answered with his eyes closed.
“Let me know if you think you are going to cum.” He nodded. She held his cock loosely and stopped stroking it. It twitched a little and then got a little stiffer. He was ready for the next stage.
That stage involved Rose lowering her head over his cock and taking it in her mouth. She had no trouble taking the whole thing. She had taken double that size before. A bit of saliva and she started working her mouth up and down. Steadily of course. It was about keeping him stiff for as long as possible without any accidents. He lasted a few minutes of this before he felt he was getting close and told her so. She backed off. The head of his cock was swimming in a saliva-pre cum cocktail. Rose licked her lips. She was warming to her task. She left his dick alone for a while to give it some recovery time. They kissed some more. Brian was really getting into this. Rose’s hands were wandering all over his body as their lips and tongues worked in unison. She looked own and saw he was still stiff. To offer more encouragement, not that he needed much, she unclasped her bra and dropped it to the floor. He tits pinged out. Not only were they full and round but perky too. She definitely had the body of a twenty year old. Brian reached up and took one in each hand. He held and squeezed them. This was helping. He was staying stiff but wasn’t cumming. Progress.
Rose resumed her blowjob. Brian grimaced and his breathing got heavier.
“I’m gonna cum now. I can’t stop.”
“it’s ok. Give me everything you have”. Rose lifted her head just briefly enough to intruct him that and then went back full throttle with her mouth. Brian was good to his word and seconds later filled her mouth with a generous load of spunk. Rose sucked him clean as he moaned with pleasure. She wiped her mouth and nodded her approval to him.
“Good job sweetie. That was awesome. I said you’d get better with practise.” Brian wasn’t convinced but it did feel awesome. He was certainly looking forward to more practise sessions.