Fucking Pantyhose

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

One blowjob after the shop had closed and her bill was halved. When they started seeing each other after that session Sandy was getting fucked regularly and well. She always went to his place and never spent the night. She barely mentioned Tony to Ronnie and then only as a friend. She didnt want to complicate her sons life with another man not related to him. She wanted to finish getting him raised to adulthood. Now April was helping her with that. Her dry spell had ended. Perhaps she could help April end hers.

"April, unless you have another documentary you'd rather watch maybe I can see if Tony knows someone he could set you up with."

"Please don't. You worry too much about me. My love life will sort itself out in time."

"Ok. I just think you need to put yourself out there more. Flaunt what you have. Lord knows I dress to accentuate my boobs. Tony loves them. You should showcase those lovely legs of yours more."

Glancing down Sandy said, "Wearing sexy stockings like those you have on is a good start. Are they new?"

With that April blushed and the food arrived.

*******

Tuesday afternoon April was wearing the lace crochless bodystocking she had on the previous day at lunch. Sandy did not know it was a bodystocking as April had a conservative blouse and skirt covering it. Sandy certainly didn't know it was crochless.

What Sandy most certainly wouldn't have imagined was that the woman wearing it would right now be astride her sons nylon trapped penis and grinding herself to a nice orgasm.

Ronnie was stroking the cougars toned thighs and enjoying the texture of the lacy swirl pattern. He was gazing at her full bush sliding back and forth along his hardon or rather the pantyhose covering his hardon.

"That feels so great April. I'm getting close again."

"I'm even closer dearie. Hold off while I come and I'll give you a special treat."

"Can I fuck you? Really?"

"No Ronnie, we will not. I've told you the reasons." April said. Her breathing was getting more rapid and she ground her clit down harder and increased her tempo.

"Will you at least suck it?"

The thought tempted her. She hadn't had a cock of any age in her mouth in a very long time and his was so vibrant, youthful, and juicy looking. It was too close to sex though and she was afraid if she crossed that boundary her pussy would follow shortly. The image of this youngster blowing off in her mouth brought her over the edge and she gushed with a very satisfying cum, soaking his nylon encased cock.

"Whew! That was fabulous Ronnie." April said as she rolled off his abdomen with a satisfied sigh.

"You are really learning control. If you can delay your orgasm while your favorite fabrics are touching you that is quite the accomplishment. You will make someone very happy young man. Are you sure there are no girls your age that would be able to inspire you?"

"There is one who goes to my third period class. Her name is Susie."

Ronnie had answered this question while watching his mom's friend strip off her sexy outfit and put on another pair of pantyhose. This pair had a crotch dammit. He wanted to ask her, even beg her to suck him. He was so close and they had been playing for over an hour. He hadn't come once and she had gotten off several times. She had let him examine her pussy with his hands and shown her all about how a woman likes to be touched down there. She showed him how to play with her little button she called her clitoris. She had let him finger fuck her while she played with her clit herself. She was so smooth and tight inside. It would feel great around his cock. He just knew it would. When he had tried to get his head between her legs to taste her she had pushed him away.

"No Ronnie. That's too much like sex and I couldn't face your mother."

She sure had a weird sense of what was and wasn't sex but he felt he better play along to get what he could get.

"What makes you like Suzie?"

"I dunno. I guess because she wears stocking a lot and has nice legs."

"Have you talked with her?"

"A little. She's pretty shy. She was new to the school this year."

"Ronnie. I'd like you to stand up and take off those hose for me."

'Oh boy', he thought. Maybe now I'll get my dick sucked. He peeled off the sheer black pantyhose with a little difficulty as his precum and her juices had thoroughly soaked the front panel.

"Now put these on and you'll get your treat." April said, handing him a new pair of crotchless lacy white pantyhose. After complying, he was standing and his erect teenage penis was bobbing at April's eye level as she sat on the carpet before the aroused youngster. He could feel her hot breath on his cock when he inched himself a little closer.

"Now close your eyes and let's talk a little about Suzie. You're going to feel some wonderful sensations on your cock and I'm going to want you to imagine her."

In truth April was a little jealous at the mention of another female of intrest but the small part of the psychologist inside her that was still operating in this frenzied state knew that it was much more appropriate for Ronnies attentions to be directed to someone his own age.

"What kind of stockings does she wear?"

"Regular black most of the time. No sexy patterns like yours."

"Does she wear skirts?"

"Yeah." He jumped a little as he felt something contact his cock. He cracked an eyelid to see that April was running a stocking over his prick. The touch was deliciously delicate and some of his precum decorated it when it passed over his head.

"Are they short skirts?"

"Sometimes. Sometimes below the knee with a little slit. I sit next to her and I can see most of her thigh."

"Does she have a boyfriend?"

April had each of her hands inside a different kind of stocking as she asked this and had started to give Ronnie an occasional squeeze and tug as the questioning went on. She would change out stockings after a short while so that he would get a chance to feel all kinds of textures on his swollen prick.

"I'm playing with your cock with all different kinds of stockings Ronnie. You'll have to tell me what feels best. Why do you think Suzie doesn't have a boyfriend? Is it because she's shy?"

April was continuing her stocking covered handjob with these questions and Ronnie was answering as best he could given his hyperaroused state.

"A little because she's shy. Some of the other girls and guys make fun of her because she has a lot of acne and she wears braces. Also she doesn't have a lot on top."

"You mean breasts? I don't have a lot on top either Ronnie."

"You have more that she does and you don't have bad skin."

"I did when I was her age."

April remembered her high school days and thought Suzie seemed to be experiencing the same kind of awkward teenage rejections she had felt in her day.

"Is she your age? Eighteen?"

"I guess so. She's a senior so probably so. Like I said I haven't talked with her much."

"You just like to look at her legs?"

Ronnie was looking at April's legs now as he had his eyes open to be able to see her stocking covered hands playing with and jerking off his cock. She was squatting on her heels before him and was still eye level with his cock. Oh how he wished she would take him into her mouth.

"That one feels the best. Oh God I'm close."

April was jerking him with a fine black silk stocking on one hand and teasing his balls with a fishnet stocking on the other hand.

"Go ahead dearie. Shoot it. Think of Suzie legs and shoot your jizz for m..."

Her sentence was cut off by a blast of his seed firing into her open mouth. She jerked her head back and swallowed. His further blasts continued and coated her face and hair.

She kept jerking his dick until he was spent and when he looked down and saw her come covered face he said.

"I'm sorry April. I didn't mean to..."

She cut him off. "It was my fault Ronnie. I was in the line of fire after all and I had built you up to that big load. I'm going to go into the bathroom and clean up a bit. Why don't you sit on the bed and work that thing up again. Keep the crotchless pantyhose on. I'm going to show you a position for fucking that most women enjoy. If you ever get a chance with Suzie

I'm sure she'll enjoy it."

When April went into the bathroom to shower off his cum Ronnie sat on the bed and stroked his immediately re-erect penis. Finally getting to fuck. He couldn't wait.

April showered off the cum and then masturbated herself to an earthshaking orgasm. She almost lost her balance and had to lean on the shower door.

When she got out and dried off she put on a pair of nude pantyhose. Over this she put on another pair which she had altered slightly. She had cut a small hole in the crotch through which his penis was supposed to slip. It would offer more friction to him than a full crotchless pair would have and the intact pair underneath would prevent his accidentally slipping inside her. She had prepared several pairs in this manner so that she could teach him various positions for sex in the weeks to come without breaking her promise to herself.

When April entered the bedroom again and Ronnie could see that she was not naked the disappointment on his face was palpable.

She joined him on the bed and getting on all fours facing the headboard she invited him to get on his knees behind her.

There was a large mirror above her dresser from which the two of them could observe all of what was about to happen from a side view and she hoped it would enhance his excitement. She knew it would hers.

"Line that nice cock of yours Ronnie with my pussy hole. There is a small hole in the pantyhose which it should fit through. I have another pair underneath so you will feel the heat and wetness of my pussy but you won't go inside. That would be breaking the rules."

'Fuck the rules', he thought, but he said. "Ok April. Like this?"

He placed the head inside the narrow slit in the hose while she held it open with two fingers. It hugged his length when he slid forward and the top side of his prick rubbed agaist her moist nylon covered gash.

"Yes!!" She hissed. "Just like that. Now pump back and forth. This is called doggy style. Most women love it. Take my hips and make belief it's Suzie and her pussy you are going in and out of. You can't fuck my pussy but you can fuck my pantyhose. Now do it. Fuck my pantyhose and make me come again."

They both watched in the mirror as he sawed his hips back and forth and fucked her pantyhose. The sight was very kinky and erotic. The teenage son of her good friend dressed in a sexy pair of crochless pantyhose fucking her doggy style. She had a hand pressed up agaist his cock while it continued it's humping motions between the layers of nylon. This kept some pressure against her clit with his fucking motions. His calves were rubbing against hers while he was fucking her and she could remember fondly a previous lesbian experience when a lover had fucked her while wearing a strap on. She and the other woman had stockings on and the memory of the swish swish of nylon against silk from that long ago time made her smile.

Ronnie was able to last quite a while after his recent explosion. It was quite the load and very tasty. She had managed to get cum in her mouth without blowing him.

'Glad I resisted that temptation' she had thought to herself.

Eventually after another good orgasm for her April could feel him thrusting harder and reached between their bodies to feel that his balls had tightened up.

"Go ahead baby. Blow that load into Suzie. Fill her up. She wants it. Wants it bad."

Ronnie grunted and ejaculated. His sperm coating the space between the pantyhose.

'Maybe this wasn't real fucking but it's not bad.' He thought to himself as he fell back in exhaustion on the bed.

*******

The next two weeks went on in a similar way. Sandy and April having their weekly lunches. They talked about men and April gave her updates on her progress with Ronnie. Very sanitized reports.

April continued her non-sex sessions with Ronnie. She taught him various positions for sex, always being careful to have two pairs of pantyhose on to prevent accidental penetration.

He enjoyed what they were doing but kept begging and asking for more.

Ronnie was being more open with his mom and related that things were going well with April and that he felt he was understanding a lot of things about himself. He told her that with April's encouragement he had asked out a girl from his school for a date and she had said yes.

"That's wonderful!" His mom had said. "What's her name?"

"Suzie. We're going to a concert week after next."

"I'm so happy son. It looks like your sessions with April are paying off. They've given you confidence."

'More than that' Ronnie thought but he said, "It sure has mom."

*******

On a Wednesday afternoon, three days before Ronnie was to take Suzie out on their first date and the day before his last scheduled session with April, Sandy made a disturbing discovery in his room.

April was home when her cell phone chimed with Sandy's call.

"Hi Sandy. How was your day?"

Silence.

"Can you hear me? Are you there?"

"Yes. I'm here. I'm a little embarrassed about what I have to tell you is all."

"What is it? We've shared a lot of embarrassing things. You can tell me anything."

"Well, um I was cleaning the house and I ahh..."

A long pause.

"Go ahead. You were cleaning the house and you..."

"I found a paper bag under his bed."

Oh no! April's heart sank as she knew where this was going. She knew what was in that bag. She was hurriedly preparing an explanation to excuse her wanton behavior when Sandy began speaking again.

"I'm almost afraid to say what I found in the bag."

Silence from April.

"There were a lot of stockings and he had obviously used them to masturbate with."

More silence from April.

"I thought they might be mine but then I knew they were not. I had been pleased that he had been leaving my underwear drawers alone these past few weeks. I was sure your helping him was getting him to outgrow jerking off on his mother's stockings but now I find this!"

April was desperately trying to formulate an answer to what she was sure was going to be an accusation leveled against her when Sandy spoke again and relief washed over her.

"I'm so sorry April. Obviously Ronnie has been going through your things and helping himself to them. I recognized one pair in particular that you wore to the cafe. He must have invaded your privacy when he found an opportunity."

April could hear sobbing coming from Sandy's end and quickly morphed from someone needing bailing out into her more comfortable role of rescuer.

"There, there. It's not what you think. He didn't steal those things. I gave them to him. We talked about his fixation on the stockings and such and I recommended desensitaztion.

I told him to use them for a while but to work towards being with a real female."

"You gave them to him?"

"Yes I did. It seems to have worked because he's going out on a date this weekend."

"I know. He told me."

"Our last session is tomorrow. Don't say anything about the bag or the contents, he may have forgotten he has it. He has made great progress. I'll tell him to throw them away after our session."

"Can they be slavaged? Some of them look expensive."

"I couldn't wear them again after what he's done with them. It would be too weird, almost incestuous. Consider them tuition. You can pick up the tab for lunch for the next few months and we'll call it even."

"Oh April." Said Sandy with very obvious relief in her tone, "Thank you again for taking care of my boy. You're the best friend ever."

"No. Thank you dear. It's been my pleasure."

*******

Thursday afternoon Ronnie arrived and had the paper bag holding her crusty stockings.

"Your mother found those under your bed." April said pointing to the bag.

Ronnies face fell and reddened.

"Don't worry. I covered for you. For us. I told her I had given them to you and that they were part of therapy. Now you have to make my promise have meaning by never again taking her stockings. Can you promise that?"

"Yes."

"Good. Are you excited about your date with Suzie?"

"Yes. We've talked about it some during lunch period. I think she's kind of new to dating too."

"You will have to be very gentle and slow with one another. Touch her very gently and read her signals as to what to do next. You have some ability to do that as I well know from our play sessions together."

"I can be slow."

"If you do have sex remember to wear a condom. I would have had you wear one if we had any penetration because I could still potentially get pregnant but since you were just fucking my pantyhose that was like the condom. You wouldn't want to get her pregnant."

"If we get that far I will. Where can I get some?"

"It just so happens I bought some for you. Here, consider them a graduation from therapy gift." She said as she handed him the box of prophylactics.

"Can I try one out with you?" Ronnie said with a hopeful grin.

"No you cannot and I will not suck you either. We have gone over that ground and I want to keep those boundaries."

She looked at his disappointed face and added.

"We can try one more practice with you fucking my pantyhose in the position of your choice."

"I choose doggy style. That felt the best when you were playing with my balls. Can we practice kissing a little too? I don't want to make a fool of myself when I first try it with Suzie."

"Well ok." April answered with very little reluctance, "For Suzies sake."

They sat down together on the couch and engaged in a serious make out session as two teenagers might which was somewhat appropriate as one of them was actually still a teenager. She taught him how to kiss, softly, then deeply and passionately. She allowed him to unbutton her blouse and first fondle and then put his mouth on her boobies.

When he ran his hand up her leg and reached her dampening pussy she did not stop him.

She was wearing silk stockings, a garter belt, and no panties for this occasion.

There was only a brief hesitation on her part when he asked if he could kiss her down there.

She had been hoping he would ask and was rationalizing in her mind that it would be to Suzies and any future girlfriends benefits if had a little training in cunnilingus. She pulled off her skirt in response to his request and slid her ass to the edge of the sofa.

Ronnie got down between her legs and she put a stocking covered calf over each of his shoulders and pulled him gently into position. Her former bush was gone as she had shaved her pussy for this occasion. She had done it this morning in the shower and had masturbated herself to a couple of nice orgasms in the process.

She had been hoping very much that he would ask to taste her. She had denied him before but it had been ages and ages since she had been eaten and the very anticipation of his tongue on her pussy was too much for her to resist.

"Wow! You're all bare down there."

"I thought it would be easier for you to see what you were doing."

When she said that Ronnie knew that she was eager to be eaten and he dove right in.

For the next thirty minutes April taught the young man the basics of eating pussy. He was a natural and she managed to have one small orgasm and one larger one.

Ronnie was very aroused and playing with his hard cock which he had extracted from his pants. When he rose up and tried to position his cock for entry she pushed him away.

"No means no young man. You are going to have to learn that. I won't leave you frustrated. Let's go upstairs and let me put on my pantyhose and you can fuck those one last time. I'll play with your balls just the way you like and you can squirt all over."