It took me almost two years to get up the courage to ask her. Demi was great in bed and had more experience than I did. She was a masseuse and loved to touch and be touched. We met after my divorce. She loved sex as much as I did, and I felt like I had been released. We had great sex, and she was certainly adventurous, but this was something new. What would she think of me?

I am pretty much a man’s man, so what would she think when I told her I wanted her to fuck me with a strap-on? We had done a little anal exploration. She had fingered my ass while giving me a blow job once, but this just seemed different. So much more out of character. Would she think I was gay or a freak? I didn’t have the guts to ask her directly.

I texted her: Have you ever pegged anyone?

She replied: What brought this up?

All the doubts and fears came swirling through my head. How do I answer? Do I tell her I’ve been fantasizing about it for years? That I have been using toys in my ass when I masturbate? The phone sex sessions where I have had women tell me how they would fuck me and how to fuck myself in lurid detail?

I replied: I watched it in a porno.

Which was true, but certainly not the whole truth.

She replied: When have you been watching porn? How often? :-)

I started to panic. Was I in trouble for watching porn? No, calm down, smiley face emoji. She’s teasing. Breathe.

Before I could muster a reply, she texted again: Do you want me to peg you!? :-)

Again, with a smiley face emoji. She was open to it. I was so excited; my fantasy was coming to reality. How should I reply?

I replied: Yes

It was a little weak of a response. I mean, I’d been fantasizing about it for years, and “yes” was the response? Gawd, I was so lame.  

She texted back: Do you have a strap-on? I don’t have one anymore.

Anymore? Had she done this before? Had she used it on a man? Or another woman? I could feel the erection growing in my pants. I don’t know if it was the thought of her fucking someone else, or just my fantasy coming true. I was hard as a rock.

I texted: No, I don’t, then quickly added, I don’t want to assume you would be in to it.

She texted back: It could be fun, but if you want to do it tonight, we have to go to the sex shop. Followed by: Come pick me up.

Tonight!? My Gawd, this was going to happen. I replied: Be there in 10.

I was in a daze. I couldn’t believe this was going to happen. Nine minutes and fifty-nine seconds later I arrived at her place. Demi was dressed in a set of leggings, and a shirt I bought her at Lulu.  Her shirt was cut low in the back so I could see the muscles on her shoulders.

Demi is almost fifty (I’m forty-seven), but she is in great shape. She teaches Yoga and was a dancer when she was younger.  She works as a therapeutic masseuse which is where we met after I tore my ACL.  She has a great butt from all the exercise. She is athletic and muscular rather than supermodel skinny. She has surgically enhanced D cup breasts which are a little big for her five-foot-five frame, but sexy as hell. I’m five foot ten inches with big shoulders and thighs. I lift weights and do some cardio. I’m muscular, not really chubby, but not rock-hard abs either (more like the dad body).

She hugged and kissed me on the lips. She had a mischievous grin on her face. She pulled me toward her and kissed my neck. I was already aroused at what was going to happen and her kissing me instantly started my erection. She slid her tongue in my ear, and whispered, “Are you ready?”

I was shocked, was she as into this as me? She seemed really turned on.

We got in the car and drove to the sex shop. The shop was a big store, almost as big as a supermarket. It was called “The Castle” and the building was shaped like a castle. The company had gone away from the seedy dimly lit sex shops of the past. It didn’t have porno booths in the back or anything like that. It did have almost anything you would want from dildos to inflatable dolls.

Almost instantly when I entered, I started getting nervous. At least I was wearing a mask due to Covid restrictions. My mind started going crazy. What if someone I knew saw me? Saw what I was buying? What would they think of me? If my buddies found out I would be the butt of the joke at every get-together. Oh God, “butt of the joke”. There would be a million gags at my expense. My heart raced.

Demi didn’t seem to be bothered. She grabbed my arm. Looked at some lingerie. She seemed so nonchalant, like we were just grabbing a bottle of wine at the grocery store.  Demi has always seemed fearless around her sexuality.  It's one of the things I love about her.  

She pointed and said, “I think they are over there.” She didn’t whisper but used her normal conversational voice. She might as well have screamed. She pulled me over to where the strap-on harnesses and dildos were. I was already mortified, but then the questions started.

"Hey Honey, what do you think of this one?” she said as she held up a harness. “Ooh, how about the red one?

“Do you think I can try it on? Excuse me, miss?” she said, waving over the salesclerk. “Can I try this on?”

She already had it out of the box and was putting it on over her leggings. I could feel my face getting red. I was just hoping to grab one and get out; Demi had different ideas. The salesgirl began helping her with the straps. She situated the harness over her crotch. It had a little nub sticking out where presumably you would attach the dildo.

“Is it tight enough?" the salesgirl asked. “You want it tight, so it doesn’t slip when you’re thrusting. This is a Vac-u-lok; is that the style you were looking for?”

“What’s the difference?” Demi asked casually as though she were comparing a cut of clothing and not something she would be using to fuck her boyfriend with later.

“Well, the Vac-u-Lok holds the dildo in place better, but it can be hard to change the dildo if you want to switch. See, this other one just has a ring, and the dildo can slide in and out,” she informed us with the same level of casualness as Demi.

Demi looked at me, and said, “Honey, do you think we will want to switch out?"

I shrugged. Well, so much for the idea that this might not be for me. Demi and the salesgirl looked at me. I felt utterly exposed. Behind my mask I could feel my face begin to flush in embarrassment. Demi was acting casually. I couldn’t see if she was grinning under the mask, but her eyes told me she was enjoying my discomfort. The salesgirl also seemed unusually interested in my response. Her eyes narrowed as she looked at me.

“I’m not sure, uh, maybe,” I stuttered, hoping I was off the hook, but NO I was not. My humiliation had only just begun.

"What kind of toy are you looking for? Maybe we can match it up to the right harness?” the salesgirl asked.

I should have grabbed the nearest dildo and held it up. Instead, I said, “I don’t know.” Which was the wrong answer!

I had fantasized about being fucked by a woman in vivid detail. However, the reality of facing a wall of dildos and two women intent on getting the exact right one was overwhelming. They were also having a lot of fun at my expense. The next few minutes were a blur of the most embarrassing questions I have ever experienced, although it started out simple enough. 

“How big do you want it?” the salesgirl asked.  This piqued Demi’s attention. She looked over at me and raised her eyebrows. I had no answer. I'd never thought about it. I used a small vibrator on myself. Did I want something bigger? What if it was too big? What would they think if I picked the wrong one? My penis is about seven and a half inches long. I have never really known if it is big or small or average. I started there.

“About seven inches,” I said.

“Oh, so you want to go pretty big?” the salesgirl asked. Followed by, “Do you want it to look like a real penis? 'Cause some men are into that.”  

“No, not one that looks real,” I said hoping to save any of my masculinity. I just wanted to get one and go, but no, the questions kept coming.

“Do you want one that vibrates?” Demi chimed in, not to be outdone. “How about this one?” she asked as she held up an eight- or nine-inch big rainbow dildo.

“You might want to start smaller and work up to that one,” the salesgirl added.

“This one has two vibrators; how about that?” someone asked.

“So, you definitely want something that vibrates? Right, Honey?” Demi asked.

“Do you want one for oral too?” the salesgirl asked.

“Oh, I don’t think he wants to suck one. Do you, Hon?” Demi asked.

"Umm, ah, I don't think so," I replied, kind of shook.

I spent the next five minutes stumbling through questions about what type of rubber cock I had my heart set on.  I felt so uncomfortable and unsure of myself, and kept looking around praying no one I knew walked in. At some point we moved on to lube.  I felt so vulnerable. I was afraid of what they were thinking about me. I thought, “What have I gotten myself into?”

“Do you want water-based or silicone?” the salesgirl asked.

“What’s the difference?” Demi asked, prolonging the adventure as the salesgirl went into a scientific explanation and how different toys can use different lubes.

“Do you need desensitizer? It numbs the area,” the salesgirl asked after we picked out lube.

“Oh, I think he wants to feel it, don’t you, sweetheart?" Demi asked so sweetly, but I could tell she was enjoying the hell out of watching me squirm.

“Oh, what about an enema ball?” the salesgirl asked, always so helpful.  I got through by muttering agreement, keeping my head down, trying to move the process along, and basically agreeing to purchase anything. For her part, Demi seemed intrigued with every piece of information the salesgirl offered. The salesgirl seemed intent on giving us every bit of knowledge and ensuring I got the right products. I wondered if she worked on commission.

I ended up with 5 dildos, including the big rainbow one, most of which resemble a penis, and 3 of which vibrate, and one for my mouth just in case), both harnesses, water-based lube, silicone-based lube, flavored lube (don’t ask), massage oil, desensitizer ('cause Big Rainbow), batteries, spare batteries, toy cleaner, enema kit, and a bag of little gummy dicks because Demi thought it was hilarious to literally eat a bag of dicks.

As we were checking out, I could see that people were staring at my purchases. I don’t know if it was what I was getting or just the sheer volume of stuff. As a final indignity, the salesgirl had to put batteries into every vibrator and turn them on, because "there are no returns on items once they are used."  She made a point of holding each one up and handing it to me so I could verify it was vibrating.  When she held up Big Rainbow, I noticed that the eyes of the two gay men behind me got wide. I would recognize one of them as my waiter two days later at a business lunch.  I noticed our table got a lot of traffic and grins from the waitstaff.

I was still anxious as I slunk back to the car with Demi. I felt so powerless and exposed the whole time.  I felt emasculated during the whole process.  I couldn’t stop thinking everyone was judging me. I looked over and Demi was grinning ear to ear which made me more anxious than a little angry. I wasn’t sure if she had been teasing me or messing with my head the whole time.  Was she just fucking with me?  Was she really going to go through with this? Or pull the rug out from under me.  I got a little sullen and silent. Basically I was pouting.

“I really like seeing you like that in the store,” she broke the silence.

“Like what? Fucking mortified?” I said, maybe a little too defensively. “Why would like to see me like that?” I asked. "Do you like seeing me humiliated?  Are you just fucking with me? And that fucking salesgirl. 'Do you like this? 'Do you want this?' 'Oh, hey, let's tell the whole store this weirdo takes it up the ass.' It was horrible." I was going from pouting to temper tantrum.

"Look, if we are going to do this, you need to get over this," Demi replied. "I'm ok with this; are you? And yes, I was fucking with you and so was the salesgirl.  Don't act like such a tight ass next time." She giggled at her own joke. She was still so cool in the midst of me freaking out.

"I just feel really uncomfortable about this. I really want it to happen, but I also don't want you to think I'm gay, or weird, or something," I stated, expressing all my insecurities.               

“I liked seeing you vulnerable in the store, because you're always so sure of yourself most of the time,” she answered. “You always have your opinions and you're always sure they're right. It was nice to see you caught off guard, not have an opinion, not in control.  Which is what this is about. I really like the fact that you are vulnerable enough to share this with me, but you need to get over it.  I don't think less of you as a man. Do you?" She rubbed my arm. "I love that you are a confident strong man, but I also like when you are insecure about some things. It makes you very human," she continued. 

That stung a bit, but she was right. I was the one judging me, not her. Maybe the salesgirl, but not her. I took a deep breath and started to relax. I realized that I really cared about Demi and the fear was I would lose her or she would think less of me.  Clearly she cared about me and was willing to do this.  Before I could make some sappy apology, Demi chimed in, "Now are you ready to stop pouting and let me fuck you in the ass?"            

She let out a diabolical laugh. Then she kissed my neck and bit my ear lobe. Instantly my anxiety vanished and became excitement. I felt my cock harden in my pants. Demi was getting excited as well; she was kissing me and began rubbing herself through her leggings. She knows how excited I get seeing her masturbate. We got to her house, and she got out of the car.

“Get two glasses of wine and meet me in the bedroom,” she spoke.

I had to pick out a bottle and open it. Typically, that would have been a quick process but I found myself second guessing my choice of wine. I took a couple of deep breaths to settle down. I picked out a nice Bordeaux and poured two glasses. I brought the glasses to the room. Demi had lit some candles, and her massage table was set up. She was wearing a lacy black bra and underwear. All the toys, harnesses, and a bottle of lube were unboxed and on the bed. She took the wine from my hand.

"Take off your clothes and get on the table. I want to relax you a little before we do this,” Demi instructed.

I set my wine down. took off my clothes and climbed onto the table. I was a mixture of nervous and excited. Demi began rubbing oil on my back and massaging me. She started rubbing my back and I began to relax. She worked her way down to my bottom and began rubbing my ass cheeks. She poured some warm massage oil down my ass crack and began sliding a finger up and down between my cheeks. She gently squeezed and massaged my balls. I could feel the erection growing underneath me. She began working a fingertip around my asshole. It was driving me crazy and I began moving my hips and butt, responding to her touch. The feeling was amazing. I felt tingly as goosebumps raised on my skin. I could feel myself shaking.

“Hmmm, just relax,” Demi said. “Are you ready for a finger?”

I turned back to look at her and just nodded my head yes. I didn’t want to talk and break the spell. She took off her bra and panties. I was already hard, but the sight of her body made me throb. She slipped on a rubber glove we had left over from Covid supplies. I turned back around and raised my ass a little. I felt more warm massage oil poured down my ass crack. I felt her gloved finger rubbing my asshole, applying a little more pressure. Then she pushed it in. I sucked in a breath as she penetrated me. She began moving the finger inside of me. Then she began sliding it in and out. I couldn’t believe how good it felt.

“Are you ready for two?”

“Yes please.” 

She pulled the first finger out and I felt myself being stretched as she worked two fingers inside me. There was a little pain as I felt my asshole being stretched.

“Just relax, breathe, relax baby,” she whispered.  I felt my sphincter relax and she pushed her fingers deep inside me. I could feel her spread them apart, stretching my asshole. I was shaking all over. The feeling was so intense. She began sliding the fingers in and out, twisting them. She would spread them apart, stretching me farther. I began to rock my hips back into her hand. I couldn’t believe how good it felt. I started moaning and rocking faster, enjoying the feeling of her fucking me with her hand. I was afraid I would come from just this. She must have known I was close because she removed her fingers. I felt a warm washcloth run up my ass. I heard the glove being removed.

“Are you ready for a toy now?” 

“Yes, I am.” 

“Hop down off the table.” 

I slid off the table and stood facing her. She looked so beautiful in the candlelight. She removed her bra and panties. She threw her arms around me and kissed me. I pulled her close and felt her body next to mine. I kissed her neck and moved my mouth to her nipple. I sucked and licked her nipple. She pushed me back.

“Later. This is your time right now,” she stated.

She grabbed a harness and light blue vibrating dildo. It was about 6 inches long and shaped somewhat like a penis. It didn’t have veins or bumps like the more realistic dildos. It did have a head and some ridges around the tip. It was bigger than anything I had ever inserted. She slid it into the harness, then placed her feet through the harness. She pulled it up and tightened the straps. I was so turned on seeing her like this. My cock was ram rod straight.

“Turn around and grab the table. Now bend over,” she directed.

I heard the cap on the lube being opened. Then I felt a cool jelly sensation down the crack of my ass. Demi squirted more lube on the dildo. I felt the tip being rubbed up and down my ass.  She grabbed my hips and teased me with the toy, building the sexual tension.  I started moving my ass up and down and pushing on the tip.

“A little lower, that’s it,” Demi said. “Now I’m going to hold it here and you push back against it.”

I pushed back against the tip of the rubber cock as Demi guided it into me. I could feel myself being stretched and there was a little pain. Demi grabbed my hips and gently pushed, the head now fully penetrating my virgin asshole. There was a release as the head pushed through, both mentally and physically.  In a strange way I felt suddenly released.  I no longer felt embarrassed.  I was just able to enjoy the experience.  Once the head was through, I was able to slide back further on the dildo. I took about half when Demi began thrusting pushing it deeper into me. She began slowly fucking me in and out, pushing it deeper into to me. She pulled my hips and penetrated me until I could feel her thighs pressed against me. I let out a moan, and she wrapped her arms around me, pulling me close.

It felt so erotic giving myself to her like this. In the porn videos the woman is usually domineering, but this was more intimate. I felt so vulnerable and safe at the same time. She ran her hands over my back, gently rubbing her nails against my skin. She leaned down and I could feel her hard nipples against my back. I reached back and grabbed the back of her thigh, pulling her into me. She shifted her pelvis and pushed against a spot inside, causing me to ejaculate a little fluid.

“Oh, my Gawd,” I moaned. It was like a mini orgasm; I didn’t shoot a full load, but it was super intense. I started shivering and breathing hard. I couldn’t believe I could come from being fucked in the ass.

“That’s your prostate; have you ever had a progasm before?” she asked.

“No, that was really intense. In a good way... in a really good way."

She pulled her cock out of me. There was a little pain as the head pulled out. I turned and faced her. My cock was still erect and throbbing. I was breathing heavily. She looked down at my swollen hard member and grinned.

“Mmm, do you want a little more?” she asked.

“Yes, please. if it’s ok.” 

“Sure, but let’s turn this thing on.”

She purred as the vibrator tickled her pussy. She turned me back around and bent me over. She squirted some more lube down my crack and pressed the vibrating head against my tight little hole. The feeling was amazing as she rubbed it up and down my crack, teasing me. I began moaning and arching my back, pushing against the tip as she rubbed it against me. She was breathing harder, and the vibrator was stimulating her pussy. She thrust into me a little more forcefully than the first time, popping the head through my hole and penetrating me. I moaned as she entered me. It felt like my whole body was vibrating. I could especially feel the vibrations in my balls and lower penis.

She was fucking me a little faster and harder, kissing and nibbling at my shoulders and neck. I was moaning like a whore as she fucked me. The vibrations pushing me over the edge. I began pushing back into her and we found a rhythm. I would push back as she pushed in. I felt her hand grip my hard cock. She began jerking me off, matching her strokes to her thrusts. Instantly I felt an orgasm building. I moaned loudly as I came, shooting a load onto the massage table. Even after I came my cock kept pulsing; my body was shaking so hard it felt like a convulsion. I had never had such an intense orgasm. I turned around and faced Demi. She was smiling from ear to ear. She slipped out of the harness and put her arms around me.

She kissed me passionately with her tongue deep in my mouth. I could tell she was turned on by the process. I kissed her neck and shoulder, then ran my tongue to her breasts. I teased and sucked her nipples. She moaned and pushed me down to my knees. I buried my face in her pussy, kissing and licking her lips and clit. I began focusing my attention on her clit, sucking it, then flicking my tongue over it. She grabbed the back of my head and began rubbing her clit on my lips and tongue. She was moaning and grinding into my mouth.

Suddenly she screamed and I felt warmth all over my face. I could feel liquid on my chin and cheeks. Her pussy had squirted liquid all over my face. It wasn’t salty, but basically tasteless. I was a little stunned because that hadn’t happened before. I looked up at her.

“I’m sorry, I didn’t know I was going to do that,” she said. “I haven’t squirted in a while. I was just so turned on.”

I grabbed a quick shower and cleaned up. then came back into the bedroom. The toys and the massage table had been put away. Demi had refilled the wine glasses and was under the sheets. I climbed into bed and we kissed and cuddled until we both fell asleep in each other’s arms. I had never felt so close to her as I did that night.  The next morning things got more interesting.