James and Lisa Spanked Together

"Pull your pants down, James." I had heard that command many times in the past, but that's not what startled me. For the first time, I was told to pull my pants down in front of another woman present for my spanking session.

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I was sent to Miss Ashley by my strict girlfriend Sandy over a year ago after what she claimed was sluggish, indifferent, unmotivated behavior on my part. She had been using different motivation and discipline techniques on me, which had limited and inconsistent results. Mouth soaping, writing lines, reading confessions to her while standing naked, and hand spankings had short-lived effects.

She confided her frustrations to a friend, who suggested she contact Miss Ashley, an experienced disciplinarian with a reputation for getting results. After consultation with Miss Ashley, Sandy told --not asked-- me that I would be going to meet Miss Ashley to devise a solution to my behavior problems. I am 23 and she is 21, but I know my place in our relationship.

We arrived at an older two-story home of colonial New England design one afternoon and had a very nice conversation with Miss Ashley. I found her to be an attractive woman of around 30, medium height and build with wavy shoulder-length brunette hair and a pleasant but confident manner.

She focused on my attitude and behavior, reviewed Sandy's previous attempts at discipline, and asked me a series of pointed questions. The whole affair was embarrassing to me since I was the subject of a not-too-favorable conversation between two dominant women who spoke as if I wasn't even there.

That consultation ended with Miss Ashley assuring us that she would produce results through her spanking and discipline methods. The consulting time did not allow for a discipline session right then, but an appointment was made for the following week. Miss Ashley told Sandy that she need not be present, but when she achieved complete control over me, she would be allowed to observe the discipline for her own use.

That brings me to today.

I arrived at my scheduled appointment and was greeted by Miss Ashley, dressed in a short black skirt with a long-sleeved thin white blouse open at the neck. Her blouse showed just the top of her cleavage, and the short skirt allowed a nice view of her firm, shapely bare legs. She wore her light brown hair in a ponytail.

We went upstairs to the discipline room I was familiar with for the past year, which was comfortable and tastefully furnished like the rest of the house. Being upstairs afforded us privacy, for which I was very thankful since her nurse had her office on the first floor.

I entered the discipline room and walked over to the usual spot in front of her large mahogany desk. Before I got to the required spot, I noticed a young woman standing just to my right. I never saw her before and knew better than to ask Miss Ashley before she was ready to tell me.

The woman remained silent. I guessed her age to be around 5'8", a bit shorter than my 6 feet, and around 125 pounds with light brown shoulder-length hair set in a ponytail. She wore a pink long-sleeve blouse with the outline of her bra visible and a pair of black slacks. She glanced at me with a shy, nervous expression; it seemed she did not expect my presence, either. Her hands were clasped behind her back as she faced the desk. By her presence alone, I knew I was in for a very embarrassing discipline session.

Miss Ashley assumed her position behind her desk and opened a manila file folder. I assumed there were two such folders, one for each of us. She spent a moment perusing the file, then looked up at me. "Pull down your pants, James."

I was surprised and hesitated, but she repeated her command and gave me "the look" that said there would be no further discussion. I looked at the woman to my right, who looked at me as if to say, Get to it!

I unbuckled my belt, unbuttoned my slacks, undid the zipper, and pushed my pants down to my ankles. I looked at Miss Ashley for guidance, and she said, "That's all for now." I stood there with my shirt ending at my waist, my white underpants on display with a slight bulge in front, and my hands behind my back, waiting for whatever was coming next.

"James, the latest report from Sandy is not encouraging, even after all this time. You've made improvements and shown promise, but your effort is still lagging. Your punishment and motivational sessions will be stepped up until you show consistent progress. Is that clear?"

"Yes, ma'am, I understand."

"The young lady standing next to you is Lisa, who is here for similar reasons. You are both here together because of a scheduling issue. This is fortunate because I believe having you suffering discipline together will enhance the effects."

Lisa looked down at the carpet, knowing she was to be the focus of Miss Ashley's attention next.

Miss Ashley picked up the other file and perused it for a few seconds before addressing Lisa.

"Pull down your pants, Lisa."

She looked horrified, even though she must have expected the command. She gave a pleading look to Miss Ashley before she looked at me with wide eyes and an open mouth. It was a non-negotiable situation, so she undid her belt and zipper, tugged the waistband over her slim hips, and pushed them down to her ankles. She was now on a par with me, her blouse ending just below her navel with thin translucent red panties on display.

"What do you have to say for yourself this week, Lisa? You've reported missing your dental appointment and bought a new skirt impulsively. Now look me in the eye and explain yourself."

Lisa, clearly shy, raised her eyes to look at Miss Ashley, dreading her explanation.

"Ma'am, I was lazy and didn't want to take the time to go to the dentist. It was just a cleaning, no important dental work. Buying the skirt made me feel better since I haven't bought a new one this year."

"I see. No self-control after six months of discipline training; you're little better than when you first appeared before me. I'm glad to note that your work as a librarian has come up to speed, though. But we have more work to do."

Miss Ashley closed the files and slid them to the side of her desk. The session was about to begin.

"Both of you, lower your underpants and panties to mid-thigh."

We hooked our thumbs over the elastic waistband of our respective underwear and slid them down to mid-thigh as ordered. Lisa caught up with me after initial hesitation, so we both ended up with our underwear in the same position. From a sharp angle, I looked over and saw Lisa had a flat tummy and trimmed light brown pubic hair. After that momentary distraction, I realized that she had an even better look at me.

I saw Lisa glance sideways and focus on my now exposed cock. It's circumcised, six inches erect, and almost two inches in diameter at the head. The head is very purple when swollen and the ridge around it is prominent. While I was not yet fully erect, I knew it was going to happen, as it usually does when being scolded before the actual spankings. At a time like this, I wished it wasn't so visible in profile, but there was nothing I could do to reduce my shame.

Here I was, standing exposed before the two women; it wasn't long before Miss Ashley came around to the front of her desk and stood to my left.

"I'm going to inspect you first, James. Face me and lift your shirt." She placed her hands on my thighs and slipped my underpants down to my ankles, where my pants had already settled. She made me step out of my pants and underpants and she slid them to the side.

"Now spread your legs and place your hands on top of your head." I did it, knowing she would have a close and unobstructed view of my cock and balls.

She bent over to look closely at my groin. She grabbed hold of my engorged cock with her right hand and moved it up, down, and sideways while her other hand cupped my balls and felt each testicle. She ended up running her fingers through my pubic hair before standing up. "Next time, I will have my nurse trim your pubic hair before your inspection and spanking."

"Now bend over towards me with your hands on your knees." When I did, she pulled my shirt up to my shoulders and ran her hands down my bare back and over my buttocks, spreading my cheeks apart. I could feel Lisa getting an eyeful of my bare bottom cheeks, my exposed asshole, and my balls. My face was burning with embarrassment. With Miss Ashley's intimate touching, my cock was now fully erect, with pre-cum starting to bead at the tip.

"Stand up and turn around." I was now facing Lisa sporting a full hard-on as Miss Ashley placed her hands inside my thighs and made me spread my legs again. I could barely look at Lisa, who had a look of astonishment on her face, mouth slightly open, not believing what she was seeing.

"Bend over and grab your ankles." I could see Miss Ashley through my legs and felt her separate my buttocks as she examined my anus and the back of my scrotum. Every time she touched me, I was afraid I was getting closer to orgasm, and that would be the ultimate humiliation. She stopped in time and told me to resume my position facing her desk.

I prayed that it was Lisa's turn to be put through the same inspection, and I was not disappointed.

Miss Ashley moved to my right between Lisa and me.

"Face me and raise your blouse." Lisa was now facing me, her blouse raised just over her bra, and her panties at mid-thigh. She looked down shyly, and I couldn't tell if she was looking at the floor or my penis. My gaze was concentrated on the thin light brown pubic hair barely concealing the slit of her pussy.

Miss Ashley stooped down, yanked her panties down all the way, spread her thighs further apart, then unhooked her pants and panties from her ankles, and put them aside. Now completely bare below the waist, Miss Ashley ran her fingers through her pubic hair above and down each of her pussy lips. She spread her lips, which looked moist from where I stood, and lightly felt the top of her slit, exposing her clit and urethra.

Miss Ashley went around behind Lisa. "Face me," she commanded. "Spread your legs and bend over with your hands on your knees." Her well-shaped bare buttocks were facing me, and I could see slightly between them. As she did with me, Miss Ashley pulled Lisa's blouse up farther towards her shoulders, then ran her hands all the way down her back.

When her hands reached her bottom cheeks, she spread them, giving me a clear view of her brown-tinged asshole and the bottom of her pussy above the perineum. This surreal scene distracted me from the punishment that awaited me, my cock fully rigid and throbbing.

Miss Ashley came around and bent down behind Lisa. "Bend over farther and grab your ankles." She spread Lisa's buttocks in order to examine her anus, running her fingers down the cleft, over her perineum, to the bottom of her vaginal opening. She inserted her index finger inside her pussy and twisted it around before withdrawing it, glistening from Lisa's lubrication.

"I see you trimmed your pubic and anal hair as I instructed, Lisa. Very good."

Our inspections were concluded with Miss Ashley's order to Lisa to resume her position facing the desk. Now, the interesting part began.

"I want the two of you to pick up your clothes at your feet. Go over to the couch on your right and remove the rest of your clothes. When you're done, come back here. Be quick about it."

We did as she ordered and removed our top clothing. Lisa turned away from me as she reached back and removed her bra. We placed our clothes on the couch and returned to our positions in front of the desk, now completely naked. I could now see Lisa's breasts, which were nice handfuls with quarter-sized brown areolae and nipples that showed signs of arousal. Since she didn't protest Miss Ashley's instructions, I presumed she was as familiar with these procedures as I was.

Meanwhile, Miss Ashley retrieved several spanking implements from a desk drawer and placed them on the desktop. She pulled a sturdy straight-backed armless chair over to just behind where we stood nervously.

"I'm going to spank you over my lap one at a time. James, you're first."

I stepped over to her right side as she sat down and pulled up her little skirt, showing me her bare thighs.

"Over you go."

As Lisa watched, I bent squarely over her lap, buttocks thrust upward, with my hands and feet touching the floor on either side. She adjusted me so my cock was gripped between her thighs and my balls rested on her right thigh.

"For your warmup, I am going to give you twenty spanks on each cheek. Since you are a squirmer, I'm going to have Lisa hold your ankles down. Lisa took her cue and knelt down behind me, spreading my legs so my ankles were held to the sides of her thighs.

"Is this right, Miss Ashley?"

"Yes, Lisa, that will do. Now don't let go."

With the naked Lisa looking right up between my spread buttocks and viewing my clenching asshole and exposed balls, Miss Ashley adjusted herself for my spanking. I was mortified, but my cock was still hard as a rock between her warm thighs.

"Now stay still, James. I will spank you twenty times on each cheek. Are you ready?"

"Yes, ma'am."

She rested her right hand on my left buttock as she spoke. She raised her hand and commenced the spanking. Smack! Smack! Smack! Smack! Left cheek, right cheek, letting a second or two elapse between the spanks to let the stinging effect register. After a number of spanks, she stopped and asked me how many I had had.

"Fourteen, ma'am."

"That's correct; you have six more to go." I was happy to hear that, because if I got the count wrong, she would start over. At this point, my hard-on was subsiding due to the discomfort, even though I could feel her thighs press against it.

She finally stopped at the promised twenty and gave each cheek a light, soothing rub. She told Lisa to release my ankles, and told me to stand up. She placed her hand on my hip and told me that there was more to come.

"Now back up and make room for Lisa. Lisa, come over here and assume James' spot."

Lisa stood where I had been, facing Miss Ashley, so I got a good look at her totally exposed backside. She gave Lisa the same instructions, so Lisa slowly lowered herself over her lap, but due to her smaller stature, with her hands on the carpet her feet would not touch the floor.

"James, I want you to hold Lisa's legs still. You'll have to place her ankles at your sides and hold them tight with your elbows."

Overjoyed at this situation, I knelt behind Lisa and did as instructed. With her ankles trapped at my sides under my biceps, I had a direct view between her legs all the way up. This position caused her buttocks to separate, giving me a nice view of her puckered anus and glistening pussy below. My erection was coming back and I couldn't fight it.

Miss Ashley rested her hand across Lisa's upturned bottom as she said, "Lisa, you also are going to get 20 spanks on each cheek. I don't want a lot of crying and drama from you. Understand?"

"Yes, Ma'am," she sobbed.

Miss Ashley raised her hand as Lisa clenched her cheeks; her hand came down smartly on her left cheek first, causing a flinch from Lisa. The smacks continued until Lisa was asked, "How many?"

"Thirteen, Ma'am."

"Wrong. The last one was fourteen. So, we start over."

Miss Ashley began anew, covering each cheek in turn until she asked once again. "Twenty," answered Lisa. "Correct. That means your warmup spanking is over."

With that, I released Lisa's ankles and she wiggled her way off of Miss Ashley's lap, rubbing her dark pink buns.

"Both of you stand in front of the desk while I prepare the next phase of your discipline."

We stood next to each other, looking at each other's nakedness and blushing bottoms. Miss Ashley was sliding the spanking bench into position where the chair had been. I didn't know about Lisa, but I had been over that intimidating apparatus before, and it didn't portend anything good.

The spanking bench was made of dark maple. At the rear were two platforms sticking out to the sides, about eighteen inches above the floor, covered with a black leather pad on each. This is where the subject knelt.

Forward of the kneelers were two upright wooden supports, one in front of each kneeler where my thighs would touch, with a four-inch wide vertical gap, wide enough to allow a man's genitalia to push through. Above that was a wide padded horizontal board that supported the spankee's lower abdomen. This board continued forward to a point on the lower chest where a woman's breasts could freely hang. Forward of that and somewhat lower, there were forearm rests on either side, allowing the victim to support him or herself.

Finally, there were leather straps on both of the kneelers, the upright supports with the male genital space, the lower abdomen support, and the two armrests. These straps assured Miss Ashley that her subject would be tightly bound during punishment. If I weren't the one being punished, it would be a sight to behold.

Miss Ashley beckoned me over with her finger.

"You're going first again, James. You know how this goes, so mount the bench."

I obediently knelt on the kneeler pads, bent over the top at the waist, and rested my forearms on the forward supports. I was ready for Miss Ashley to strap me down.

"Lisa, come here. I want you to strap James to the bench while I get another implement. Make sure the straps are tight."

Lisa began buckling the straps over my calves on the kneelers. The kneelers were spread far enough apart to ensure my buttocks were spread and my balls were visible between my legs. When she pulled the strap around my thighs, I felt her hands inside of my thighs and her bare skin touching the backs of my legs. She seemed quite familiar with the bench.

When she leaned over to fasten the strap over my back, I felt her nipples brush my skin; then her nipples grazed my shoulders when she finally fastened my forearms. I could only see her from her waist down as she moved around me.

Miss Ashley came back and checked all the straps for tightness. "Good job, Lisa," she said. "Now stand behind him while I carry out his discipline."

Miss Ashley picked up a wide, firm, brown leather barber's strop with her right hand as she ran her hands over my taut cheeks with her left.

"Are you ready, James? You know this is going to hurt." She said it in her usual upbeat manner, signaling that she really enjoyed her work.

"Yes, Ma'am." My voice already quivered, knowing the pain that was imminent.

I could sense her take a step back, wind up her right arm with the strop, and then it hit. Hard. Smack!

"Oowww! One!" My whole body rippled with pain, but I couldn't escape it. Left cheek, right cheek, and so on as I squirmed.

She kept at it slowly until I counted twenty. I was fighting the straps the best I could, and was between sniffling and sobbing at the end. My ass was on fire. She allowed me to recover and then began unbuckling the restraints.

When I was given permission to dismount the spanking bench, I slowly backed myself off to the rear. My erection was gone, but I wasn't even thinking about that. My focus was on my sore butt cheeks as I rubbed them lightly.

"Your turn, Lisa. Mount the bench and stretch out."

Lisa did as instructed, placing her knees on the pads and stretching over the top. Her breasts cleared the edge of the top rest and hung down freely as she placed her forearms on the front supports.

"James, please strap Lisa down for her punishment."

I was eager enough to do that, since I was relieved my strapping was over. I began with her calves, and from that vantage point, I noticed that her butt cheeks were stretched taut. Her spread legs caused her ass crack to yawn wide open, exposing her taut pussy and brownish asshole, both with light brown hairs visible.