My wife Amy and I were interested in buying a horse so we started looking around for people with horses. We found an ad in the local paper of a couple that lived about twenty miles from us that sold horses and called them to see if we could come out to check out what they had. They were friendly over the phone and we set up a time on Monday after Amy got off work.  

We followed the directions to the Adair Ranch and when we got to the gate we were impressed. It was a beautiful steel structure that looked like it had a herd of horses running along the top of the 20 ft tall gate posts.

When we drove up to the barn, we met Tom and Betty. Tom shook my hand and tipped his hat at Amy and Betty smiled and in a friendly voice welcomed us to the “Running Horse Ranch.” They were graceful, kind and understanding of what type of horse we were looking for.

Tom and I walked behind our wives and I noticed Tom, who appeared to be in his mid-sixties staring at my wife’s tight ass in her wrangler jeans. I couldn’t help but smile, because I was looking at his wife’s ass too. For a woman of her age, she was built very nicely. A few years ago when I was younger she would have fallen into the category of a MILF!

We talked along the way and about three stalls into the barn Betty stopped and opened the gate and led a beautiful Palomino out for us to look at. It was an amazing horse. Gentle, steady and friendly. After checking out that horse for a few minutes we came to the next stall and again Betty opened the gate and led out an Appaloosa. This horse was a little more excited and pulled back against the rope as Betty tried to steady it.  We immediately passed on this horse because we didn’t want one that we would have to play rodeo on every time we tried to ride it.

The next horse was a slick-colored Sorrel. It was a three-year-old stud but was broke, gentle and ready for whatever we would want to do on it. We led that horse around the round pen and Amy even rode him bareback and the horse proved to be as gentle as a kitten.

Once the horse was put back into the stall Betty and Amy went into the house to leave us “Menfolk” talk as Betty put it. Tom moved a short distance away from me when he bent over to pick up a brick of hay I noticed that he was wearing a thong. Not just any thong, but a lacy lavender-colored thong.

After Tom put the brick of hay into the sorrel pen he turned around towards me and saw me smiling at him. He asked me what I was smiling about and without any hesitation, I told him that I had seen his pretty lavender-colored thong.

Tom tried to make some excuse that I must be seeing things because he didn’t wear thongs, and I just smiled and said, “Tom, I know what I saw. In fact, I want you to see something.”

I unbuttoned my jeans and slid them down over my hips and his eyes widened when he saw that I was wearing a thong too. Tom looked up into my eyes and unfastened his belt and jeans and pulled them down revealing a very heavy-looking cock with a huge pair of balls hidden in the sheer material of the lavender thong. We didn’t do anything at that moment except stare at each other’s cocks encased in our respective thongs and we formed an unspoken bond.

I heard Tom’s voice ask, “How did you come to be wearing women’s panties, my friend?”

I looked directly at Tom saying, “Well, my wife jokingly one night dared me to put on a pair of her panties and I did. She saw her tiny little thong panties cutting into my ball sack and my cock head sticking out of the top and said that will never do. The next day when I came home from work there was a bag on the bed with a note that read, Baby, get a shower and put one of these on before I get home. I want to see you in these pretty panties. I did as the note said and waited for my wife in my favorite recliner and when she walked into the living room she saw me and told me to stand up. Once standing, she came over, inspected me in my thong and even slapped my right bare ass cheek. She said that she approved and from that day forward I have been wearing pretty women’s panties everywhere I go.”

Tom smiled saying, “Damn. You must be a little pussy whipped, otherwise, you wouldn’t have done what your wife told you to do.”

I started to get upset but Tom cut me off saying, “I’m not making fun of you. I just want you to know that I wear thongs because I chose to before I met Betty and I let her know from day one that I will wear them and she will, too. At first, she didn’t like thongs but soon she grew to love them as much as I do. You see, I’m not pussywhipped. In fact, my wife services me anytime and anyplace I want her to. I bet your wife only services you at your home.”

I had to think about that for a few minutes but I came to realize he was right. I wear thongs because Amy wants me to, not because I chose to and we only engage in sex in the confines of our own house.

Tom looked at me while he pulled his jeans up saying, “We better go to the house before the women start wondering what we are doing.”

I agreed as I pulled up my jeans and together we walked up to the back door of their farmhouse and entered the mud room. We took off our boots and found our wives sitting at the dining room table drinking cold iced tea.

After Tom handed me a tall glass of tea they asked what we thought about the horses and we both agreed that we loved the Sorrel and Palomino but weren’t interested in the Appaloosa.

Tom chuckled, saying, “That makes total sense. We wouldn’t want anyone except an experienced cowboy to get that horse. He is a tiger when you put a saddle on him. I don’t even ride him. I have a young hand that comes around three days a week to try and break him a little more.”

We sat there chatting about everything from family to work and it was decided that I would come out the next morning and ride the sorrel and see if I liked it.

We said our goodbyes and Amy and I enjoyed the drive back home as we discussed the possibilities of owning our own horse and being able to go out trail riding and enjoying the thousands of acres of state-owned land around us.  

The next morning, as usual, I got up and saw that Amy had laid out a pair of jeans, a T-shirt, and a pretty light blue thong for me to wear. I looked at her and saw that she had chosen a matching thong and bra set that were also light blue and asked her why she had done that.

She just giggled saying, “I want you to know what I am wearing today while you are riding that horse. I want you to think about me and know that my pussy is going to be wet, knowing that your cock is going to be rubbing up against that huge saddle horn today.”

We both showered, dressed and got into my truck and I drove her into town to work. We kissed just before she headed out and I heard her giggle again saying, “Have fun, baby. I know you will.”

I didn’t have time to ask her what she meant by that last statement because she quickly walked into the secure door of her office building and disappeared.

I arrived at Tom and Betty’s house at 6:30 am and noticed lights in the barn. I parked close to the barn and saw Tom saddling a horse and noticed that two other horses were also saddled. When I asked him why three horses were saddled he told me that he and Betty would be riding along with me today. Tom also said that we should be back around 9:30 or 10:00 am and I should be able to decide if we wanted the sorrel by that time. If not, we would schedule a ride on the Palomino for the next morning. I told Tom that I was ok with that plan and waited until he finished saddling the sorrel.

Tom finished the saddling and started to walk towards the house saying, “Come on in. Betty has some breakfast prepared for us. Can’t go on a ride on an empty stomach. I walked beside Tom until we got to the house and then followed him inside. Again we took our boots off in the mud room and walked into the dining room, sitting down at the table as Betty started to bring food over.

When Betty bent over the table to set down some biscuits and gravy I noticed that her robe was handing low and I could clearly see both of her beautiful tits. Tom noticed me staring and laughed saying, “Betty, he loves your naked tits.”

I blushed about ten shades of red because I had been caught staring at this older woman’s naked tits that were within arm’s reach of me. I was brought back to reality when I heard Tom ask, “Doesn’t she look good, James? I’m glad you like looking at her.”

I was shocked at his words and for being caught but couldn’t deny my desire to get closer to those beautiful mature tits. Tom again spoke asking, “Well, James. Do you like her tits?” Betty then said, “I don’t know, Tom. It seems like the cat has got his tongue.”

I looked at Betty then at Tom as I lowered my eyes towards my plate and softly said, “Yes, I like her tits. They are beautiful.” Tom burst out laughing as she said, “Speak up, boy. Tell us what you are thinking.”

I just about screamed at the top of my lungs that I like Betty’s tits and I think they are beautiful before Tom said, “That’s better, boy. Don’t ever be shy around here. If you think something then say it loud and proud.”

Without another word, Betty reached for the sash on her robe, pulling it free then shrugged her shoulders, letting the robe fall to the floor. This beautiful 60+-year-old MILF woman stood in front of me in just a very tiny thong that barely covered her slit. It was tiny. So tiny that it was hard to see and it matched her cream-colored flesh. Betty was clean-shaven and her lips glistened behind the thin material of that tiny thong. I recalled that my wife had thongs that small and she referred to them as micro thongs. She said that all they are good for is covering the opening to a woman’s pussy. I now understood why they say that’s all they are good for, because everything except the opening to Betty’s pussy was clearly visible.

Tom looked at me as he stood up, unbuckled and unzipped his pants letting them fall to his knees. He unbuttoned his shirt and pulled it off and I saw him wearing a very sheer solid black thong that encased his cock and balls perfectly. I recalled seeing him this way yesterday in the darkened barn, but now, in the light of the dining room realized he was much bigger than I first thought. 

My cock started to stir as Tom smiled at me, just before he sat back down. My mind was brought back to reality when I felt Betty's hand on my shoulder, her voice gently saying, "I understand you wear women's panties too. I want to see."

I looked up into Betty's mesmerizing eyes as her hand caressed my shoulder and I slowly stood up. 

I unbuckled my belt, unfastened the button on my jeans and unzipped them. I slid them down over my hips and I heard Betty take in a deep breath when she saw the satin white G-string that my wife had insisted I wear today. My cock was already starting to swell and my balls were tightening and I stood there as Betty's hand slipped down and cupped my junk. 

Betty moaned as she looked at her husband saying, "He's all man, baby. He has a very nice cock and a big set of balls that look perfect in his panties. His cock is only about five inches long but that’s ok, not everyone can be hung like you."

Betty let my cock and balls go then left the room. I was in a daze as I sat back down at the table and started to eat the breakfast before me. After eating, Tom stood up, pulled his pants up and put his shirt back on. I then stood up pulled my pants back on and followed Tom back into the mud room where we put our boots back on before walking out to the barn.  

Betty came out wearing a pair of Wrangler Jeans that looked like they had been painted on her body and passionately kissed Tom. Tom helped Betty up into the saddle as I mounted the sorrel. Once Tom was mounted we rode into the wooded area of their ranch. 

After we had ridden for just over an hour we went back to the barn and as Tom was unsaddling the horses. Betty moved over close to me and softly asked me to strip. I don’t understand why I did it, but I willingly did so.

She looked at me, touched my crotch and even let her hands and finger roam over my exposed ass cheeks as we watched Tom unsaddling the horses. Tom finished and I heard Betty instruct Tom to strip. Tom smiled as he stripped down to his thong and he looked at his wife, saying, “It’s your turn, baby.”

Without hesitation, Betty stripped, leaving only her bra and panties on. 

At that moment, it became apparent that Betty was in control. Tom and I both knew it. She had us stand in front of each other and was slowly playing with our cocks and our asses through the thin material of our thongs.

Betty looked up at Tom saying, “Kiss him, baby. Make him your lover.” 

It felt weird when Tom’s lips met with mine, but I didn’t pull back. Tom's tongue probed and slid around in my mouth like a woman's would have and mine did the same, exploring his oral cavity. We kissed for long seconds as Betty encouraged us to touch each other. 

I felt like my life as I knew it was slipping away and wondered just how far this hot sexy couple was going to take me.

My hands tentatively touched Tom’s body until I felt more comfortable. Then I got into it all. My hands roamed freely over Tom’s body, feeling his cock, his balls, his ass, his back and his tongue driving me to sexual delirium. When Tom grabbed my ass he pulled my body to his and began to grind his groin against mine. Our cocks rubbed against one another through our thin panties and I could feel pre cum seeping out of the tiny slit at the end of my cock. 

Betty, unbeknownst to me, had gotten a blanket out of the tack room and laid it across a bale of hay and was leaning back, playing with her own pussy.

After watching us for several minutes, she said, "Okay, boys, it's my turn.” Betty had Tom get on his knees between her legs and eat her pussy while she sucked my cock and I felt I was in heaven. I watched as Tom slurped, lapped and licked at this beautiful woman's cunt and made her cum while she engulfed my cock down to the root. 

When I was ready to cum, she pulled my cock out of her mouth, jacking me off onto her tits. After she had an intense orgasm she instructed Tom to clean my baby cream off her body with his tongue.

I thought we were through, until Betty told me to kneel over her so she could suck me again. She wanted me to eat her pussy until she came. While I was eating her sweet pussy I felt her soft hands wrapping around my ass cheeks. Her fingers traced up and down my crack and this was driving me crazy. I concentrated on making this beautiful woman cum. I wanted to taste her juices and by the feel of it, she was trying to suck my next load deep into her throat. 

As I continued to suck on Betty’s pussy, I felt something cool being dripped onto my ass but didn't know what it was. I tried to look but Betty held my head in place by her strong thighs so I couldn’t turn my head to see what was trying to invade my asshole.

Soon I felt something slipping into my ass and later found out it was the handle of a riding crop. Betty was fucking my ass with a riding crop and I was loving it. I realized she was loving it too because she stopped sucking my cock long enough to say, “That’s a good boy. I love fucking your sweet ass. Thank you for letting me do this to you.”

My cock was rock hard while she fucked my ass. Suddenly she pulled the crop out and something much larger tried to enter my ass. I felt skin touching my ass cheeks and the back of my thighs. When I pulled my head up from between Betty's relaxed legs I saw Tom smiling down at me. He didn't say a word as he slowly shoved his thick cock into my ass, taking my boy pussy for his own. 

My ass was being stretched wider than it had ever been, and I started to wonder if I was going to be able to take all of his cock. Tom saw the look of concern on my face and assured me that he was going to make me enjoy his huge cock before the day was over.

I screamed, "Tom, this is the first time I have ever had a cock in my ass. Please, don't do this. I’m a virgin." I was in pain as the big bulbous head of his cock finally pushed past my anal opening. Tom held his cock there, allowing my muscles to relax so he could continue taking my anal cherry. 

Slowly Tom started to push again and I realized that he didn't care about my pain or concerns. He wanted my ass and he was going to get it.

Betty sucked on my cock harder, trying to make me relax and focus on her blow job. I was in pain but already feeling some pleasure from the invasion of Tom's cock. I realized that I was there to be used as they pleased for as long as they pleased this morning. This was a calculated and planned event. I just didn't know at the time who all was in on the planning.

I submitted to Tom's anal fucking and soon felt his balls slapping against my ball sack. He was all the way inside my ass now as he said, “Get ready to be fucked, my lover boy. You will make love to Betty, and FUCK me anytime we want you after this. You will want my big fat cock in your boy pussy from now on and you will be bringing your wife out here to share her tight ass too.” 

Tom sawed his cock in and out of my asshole turning the pain into total pleasure. I started to push back against Tom's thrusts, practically begging him for more cock and he laughed saying, "See Betty, I knew this young man would love cock in his ass. I knew he wanted my cock and you were right, we could seduce him without his wife here to stop us."

It was then that I realized this was all set up and orchestrated by Betty after Amy and I had left yesterday.

Tom fucked my asshole freely now and I pulled my head back up screaming, "Fuck me, Tom. Fuck my ass, make me your pussy boy." I don't know why or where that came from but at that moment I didn't want Tom to stop fucking me. And Tom didn’t.

Tom grunted, saying, "You will be my pussy boy anytime I want you now. You belong to me and Betty and we plan on using you for years to come."

Tom proved to have outstanding stamina as he fucked me. Other men would have already cum but not Tom. He was intent on making me his slut boy and I was willing to be in for the long ride.

I felt Tom’s cock swelling inside my ass, then heard him grunt saying, "Take my cum, my little pussy boy. Your whore ass belongs to me and Betty now. Your wife will be next and when we take her, you will be there to watch what we do to her slutty pussy, ass and mouth."

I felt Tom's boiling sperm flooding my ass passage. It was hot and soothing. It filled me completely and I felt sorry that it was about to be over.

Tom held his cock deep inside my ass, not moving, allowing every drop possible to drain into me. As his cock slowly softened and fell free of my stretched asshole, Betty let my stiff cock fall free of her mouth. 

Betty, still in control, said, “Jack off onto her stomach, James.”

I was so horny and needed relief that I did as instructed.

Tom had moved out from behind me and once my cock was flaccid again I stood up and looked down at the large pool of cum on Betty’s belly.

Betty smiled at me saying, “Lick up your mess, baby. I don’t think you want me to be dirty with your cum all over my body all day, do you? I obediently leaned down and cleaned up my own cum.

As I sat back and looked at Tom, I saw his cock still hanging in front of his body.

Tom was smiling when he said, "The next time you come over, or that I see you, you will suck my cock before I fuck you. Betty will give you an enema and clean your bowels out before I fuck you so you can clean my cock after I fuck you. Do you understand?"

I obediently nodded my head that I understood and watched as Tom got dressed leaving Betty and me in the barn alone. Before I left Betty had me eat her pussy, making her cum and then lick her asshole. She loved having her asshole licked. She even said that she was proud of me for the way I accepted today and took her husband’s beautiful cock.

I'm no longer an anal VIRGIN, my friends. Tom and Betty made sure of that this morning.

I later found out when I met up with my wife that she had a nice private talk with Betty when they went into the house yesterday evening. Amy admitted that she told Betty that she wanted me to be fucked in the ass by a man and explained that I wear women's panties. 

I asked her why she would divulge all of that to Betty whom we had just met the day before. Amy said that she felt very comfortable with Betty. Betty had told her about her’s and Tom’s sex lives so she felt she should do the same.  Amy said that during that conversation she found out that Betty’s husband was into fucking other men. He was considered a Male DOM and loved to stretch other men’s assholes out and make them his subs.

Amy said Tom is known by many other men as being a bisexual top (only top) and that he helps other men and couples understand their potential when it comes to bi-sexual sex. The next thing Amy told me really shocked me. Betty named three other men in the community that we know very well from Church or from our jobs that submit to Tom and Betty’s desires.

I asked Amy if she knew that Tom and Betty had plans to use her for their sexual pleasure too.

Amy blushed as she said, "Yes, darling. That's why we are going out to have dinner with them on Thursday night. They are going to use me while you watch and you are going to suck Tom's cock and get him ready to fuck me over and over again all night long since we are all off on Friday." 

I am still in shock. In just a short time yesterday, my wife and with Betty’s conniving had set this up, had me used, and I lost my anal cherry to an older man who knows really how to use his cock. 

By the way, I found out that Tom's cock is almost ten inches long and is just about three inches thick/across. I know this from a picture my wife showed me that was sent to her by Betty. The picture had a ruler laying below Tom's cock and a tape measure laying across it. The tip of his beautiful cock was at nine and 15/16 inches and the tape showed his cock to be 2 7/8 inches across.  I couldn't believe that I had that huge cock inside my asshole. No wonder I am a little sore today.

I hope you enjoyed how I lost my anal virginity. I know I did.