I returned to my life of seeking couples with bisexual men to rebuild my ego after being rejected by Rebecca. It was toward the end of my corporate life, although I didn’t know it at the time. We were building out a new logistics center in Aurora on the western outskirts of Chicago. My boss asked me to move there to take on this lengthy project, but I had purchased a house at the ocean and I didn’t see trading in the ocean for a big lake as a good trade, so I politely declined. That meant taking an early flight to O’Hare every Monday and returning late on Friday. I would get to enjoy my house at the ocean only two days a week for a period of six months.
This situation also meant that I couldn’t have any real relationships because I wasn’t fully living in either of the places where I was sleeping. I decided to see what I could find for entertainment in the Chicago area where I was residing in a long stay hotel in Aurora. Through good fortune I was able to locate Sally and Joe. They had a most intriguing profile on a site that I used for meeting couples. “Never apologize for who you are,” was the heading. Those words rang true for me and suggested that here was an enlightened couple. After the challenge with Rebecca, I might gain some insight from these two people.
I wrote an introduction to them and included my face picture. Sally responded quickly and expressed an interest, including my massage. We wrote back and forth a couple of times and I learned that they were married for more than 35 years and were in my same age bracket. She was short and he was tall. She was straight and he was bisexual. My kind of people. We made a plan for them to come to my hotel room for massage and then we would see how we felt.
It was a lovely Wednesday early evening at the beginning of Spring. There was a true sense of rebirth in the air when I had taken a morning walk around the parking lot of the hotel. Forsythia was proudly displaying yellow leaves and shoots from bulbs were poking up from the ground. The buds on trees were about to burst with life’s powerful energy. I was looking forward to meeting my new unapologetic friends that evening, but work would come first.
They arrived at the appointed time and brought a small basket of lotions and soaps. Sally was a hairdresser who graced me with a good supply of sample products from the business. She was very sweet and old fashioned in feeling the need to bring something when visiting. She was a small BBW with short black hair and a warm open smile. Joe was taller than me with a good athletic build and a full head of wavy light brown hair. I wondered if Sally did his hair but I didn’t ask.
We sat in the living room space of my room to get to know each other before deciding if we would proceed to massage. I had a bottle of wine opened to share with them. In the last six months Sally had lost sixty pounds and was working on losing another twenty. I was impressed with her determination and forthright openness. Joe was not very talkative but seemed very proud of his wife. It was not long before I sensed that we were all comfortable and I explained that my massage was best done with the person totally nude, but if Sally wanted to keep on some items that would be OK.
I had set up some towels on the bed and encouraged Sally to get as comfortable as she was able while I put on some light music for the massage. She chose to keep on small black panties and a large black bra to keep her big orbs contained. Joe had stripped to just his dark boxers and was sitting in one of the side chairs near the bed. I knew that he was well endowed, but there was an impressive bulge tenting those shorts.
I started the massage with Sally face down and I placed my hands flat on the small of her back to connect with the chi. My Reiki trained hands got very warm with healing energy right from the beginning. She had true white girl skin and my tanned hands made a significant contrast. I felt her relax into the bed as she made the typical “mmmm” sound that coincides with Reiki.
Sally still had a very large bottom and the stressed calf muscles that typically accompanied a person who carried abundant weight. Both of those areas needed significant help and I was able to make them relax and feel better. When I asked Sally to turn over for the other side of the massage, she decided to take off the bra and expose very large breasts with big nipples. She smiled invitingly while moving into a supine position.
I began with my hands flat on her pale, soft abdomen, but I didn’t hesitate to massage all over that pulchritudinous chest. These were not sexual moves, but sensual. It seemed to me though that Sally was having sexual ideas as her legs spread wider inviting me to massage the inner thighs. My hands moved confidently into that area and I used light strokes to stimulate the energy paths leading to the sexual parts. I could see that the black panties were getting darker in all the right places. I gently touched the wetness and then applied some pressure before moving my hand back and forth over the area.
Sally’s breathing began to quicken as she moved into full arousal mode. I slipped my hand down inside those black panties and gently rubbed the labia which were fully wet. I pressed in gently and located the clit which caused her to gasp with excitement. I rubbed the clit with increasing pressure and speed and it was not long before she gushed warm fluid into my hand and onto the towel below. “Sorry about that, I forgot to warn you that I squirt big time.” “I thought that you didn’t apologize for who you are.” She laughed saying, “I’m apologizing for not warning you. There’s no stopping my squirting.”
Joe joined us by taking a position behind his wife where he could hold her head and kiss tenderly while squeezing her breasts. She happily accepted the attention of two handsome men and removed the panties which were quite wet. I sucked on one of the expansive nipples while my hand continued to stimulate the clit. When I inserted my middle finger and located the G spot she tensed and gushed another warm orgasm on my hand. The aftershock came with a full laugh as she totally let herself enjoy the endorphins of the moment.
Sally reached down and rubbed my cock through my light shorts and there was a ready response which pleased her. I took off the shorts and walked my dick up to her waiting mouth. She hungrily took me into the warm wet space and sucked hard on the shaft. She had really good oral skills and I was impressed. Sally was really stimulated by sucking on my cock while I fingered her pussy. She took my long shaft all the way to the base without any gag reflex. There hadn’t been many women who could do that.
Joe dropped to his knees and I pushed my cock into his face while I kept my hand on Sally’s wet pussy. He eagerly took my cock and cupped my balls. My dick went to the back of his throat and he licked his lips as precum made its way to his mouth. Sally encouraged him while he sucked me and I saw that it excited her to make her man happy and fulfilled. “Suck that big cock. Take him all the way,” she directed Joe. I wondered how long they had been playing like this.
Both of them had such good oral skills but I didn’t want to cum yet, so I pulled back. I bent over Sally and put my head between her legs to lick the wet clit. She got excited when she discovered what I was doing and pushed her pussy up closer to my face. Joe took off his shorts and I understood how his wife had developed such good oral skills. His dick was at least eight inches and quite thick although not fully hard. He pushed his dick into her mouth and she was now sexually entertained at both ends. It was not long before I had to pull my mouth back as she squirted a huge amount of fluid while screaming her orgasm openly for the world to hear.
“Oh, you bastard,” she happily called to me in appreciation. I moved to Joe and got on my knees to see if I could take his huge shaft into my mouth. I opened wide and he slid part way in for me to get used to the thickness. It felt as big as it looked and I unsuccessfully struggled to take him all the way. “I see how you got such good oral skills,” I said to Sally and she laughed easily. She came behind me and pushed my head further onto his cock. “Come on, you can do it,” she encouraged while enjoying some dominance.
She held my head in place while he pushed his dick deeper and my eyes opened as wide as my mouth. Damn he was big. I would never be able to take him anally. I gagged and he pulled back but she still kept my head in position for him to push in again. I knew that the only path forward was to just relax and take him so I focused my breathing to calm myself and accept being used. Soon he was thrusting himself comfortably in and out of my slobbering mouth while she said, “See. I knew you could take him. Good boy! Now I’ll give you your reward.”
She positioned herself on her back with legs up in the air and a wet pussy fully opened and exposed. My cock responded naturally and stiffened in anticipation of a good fuck. I climbed over to her and lifted her legs further back so that I could slide my hard shaft inside that enticing pussy. She was so hot and my dick slid in easily. I loved the vaginal muscles closing firmly around my shaft. I began slow rhythmic thrusts while still holding onto her legs. “Fuck me hard,” she directed and I happily followed the guidance. Joe moved so that he could suck on her nipples while I fucked his wife.
I thrust my hard cock deep into her pussy and smashed my balls against that wet ass. She closed tightly on me but my dick was hard as could be and I kept on pushing in and out with force and intention. My balls got so excited smacking against smooth white ass that I knew I would cum soon and warned her it was close. “Do it. Give me your fucking cum.” Those words took me over the top and I shot a huge load of cum into her sweet fucking pussy. It was such a good orgasm that I masturbated to the memory of it the next day. “That’s a good boy,” she complimented me while smiling fully.
As I let go of her legs and collapsed on top, she reached around and gave my smooth ass a hard smack that resulted in an orgasmic aftershock. The sting from her hand was real and I was glad that she wasn’t fully spanking me because it would’ve hurt. She had very strong hands which made sense for a hairdresser. I exhaled a huge amount of air and kissed her sweetly on the mouth once my breathing normalized.
The three of us now lay on the bed with Sally in the middle and both men snuggled up to a large breast on either side. What a fine threesome. We only stayed in that position for a couple of minutes before Sally moved to straddle her husband. Instead of sitting on his big cock, she positioned her pussy over Joe’s mouth so that he could lick the cum that I had put there. “That’s a good boy. Eat it up,” she encouraged.
When Sally was sure he had taken it all she slid down and pushed his big cock inside. She rode him like a wild cowgirl with large breasts bouncing up and down just as her pussy was doing on that thick cock. I reached over and twisted one of the nipples hard but she said, “Do it harder!” I did as commanded and she gushed an orgasm on her husband’s cock. He pushed back hard up inside and shot a load of cum deep in that orgasmic pussy. She collapsed onto him and kissed him hard on the lips. Joe’s dick was so big that he didn’t slide out of her until she returned to the position between us on the bed. What a wild woman!
We relaxed together on the bed for five minutes or so before I asked, “How long have you been doing threesomes?” “It’s all his fault. He’s the one who changed,” responded Sally before Joe could answer. I learned that a little more than a year ago Joe had come to his wife to let her know that he was certain his sexual interest was now including men. It was a brave step for a man to do, but he trusted his wife of more than thirty years.
Sally was completely surprised by the statement because Joe was so masculine and hadn’t indicated any changes prior to their conversation. After initially freaking out, she calmed down and looked at the situation. She was still very much in love with Joe and didn’t want to be separated from him. She did research on the Internet to learn more about bisexuality and made an appointment with her gynecologist. She needed more data.
Sally confided in her doctor who recommended getting tested for HIV and STDs which was a good idea. Joe also was checked and both had negative results which increased their comfort zone. Joe declared that he hadn’t actually acted on his new sexual drive but was clear that he was wanting to take a path of discovery. Sally decided that they could have threesomes, as long as she was present and included. They would look for a man who was not connected to their area. As a visitor, I was a perfect fit for them. I wouldn’t pose a threat to their relationship and wouldn’t know any of their friends. Their secret would be safe.
They had been with a couple of other men but they hadn’t been fully attracted to either of them. Sally was discovering that she rather enjoyed having another man in the mix. She had only been with Joe her whole life and a new frontier was opening. She looked at sex in a way that had never occurred to her before. It could just be for fun! She was also discovering a dominant streak that hadn’t been explored before. She enjoyed telling men what to do and to reward them if they did it right the first time. Punishment was also available if warranted.
It was getting late for all of us who had work in the morning. We made a plan to meet again in two weeks and Joe would be the one to get massaged during that session. Sally gave me a sweet kiss on the cheek and Joe provided a firm handshake as we said our farewells at my door. I was glad that I was in a hotel where I would get clean towels the next day since the ones we used were really wet from Sally’s squirting.
Sally and Joe in Chicago 2
During the two weeks between sessions Sally wrote a few times to express what a great time she had had and was looking forward to our next session. “Your hands got so warm and they made my pussy feel really hot and great. How do you do that?” I explained that I didn’t have a lot of control over the Reiki energy and that when I did the moves I was trained, it just happened. I also explained that the pussy Reiki was not a part of the regular curriculum but something I discovered over time.
I told her about one incident with a woman where I had my right hand flat against her wet pussy and my left hand was on the left breast. An arc of electricity leapt between my two hands right through her inner organs. “Did you feel that?” I seriously asked. “How did you do that?” was the question that I got asked then and have had repeated by others. It was a remarkable dance of energy. Life was great!
We planned another early evening for our second session and they were as punctual as the first encounter. When I opened the door to my room, Sally kissed me passionately on the lips and lingered there before releasing me. She also reached around and squeezed both of my ass cheeks. I was surprised to receive that level of kissing from a married woman in front of her husband. It was very hot. Joe was carrying a plate of fresh vegetables and dip. He just smiled and held out his hand for our manly handshake.
I had a bottle of wine ready and we sat in the living area with our snacks for about ten minutes to catch up on our lives since the last meeting. It was pleasant to have a social time with them in addition to our bedroom events. It provided a sense of humanity to the corporeal nature of our relationship. They were good, ordinary mid-Western Americans who were becoming less and less ordinary.
Joe had no problem being naked for the massage and I began with my hands flat on the small of his back just as I had done with his wife. He had a broad back and good muscle tone including some decent biceps. As a person who had studied anatomy, I appreciated good muscle definition and sometimes the Latin names popped into my head as I worked each muscle. Joe really needed muscle relaxation. I felt anxiety or a memory stuck in his shoulders that I couldn’t get released. The muscle relaxed but the emotional element that had attached itself there resisted my attempts to set it free. I sensed that it was related to his bisexuality but it could have been anything going all the way back to his childhood. Muscles can hold memory and trauma for a long time. Often it stays lodged until we are strong enough to come to terms with the original event.
When I asked Joe to turn over, his cock was engorged but not fully hard. I encouraged Sally to come assist with this side of the massage and I could tell that Joe liked that idea since his cock added another level of stiffness. She kissed him sweetly and rubbed his nipples while I worked on his legs. She leaned over and bit his nipples which must have been a good bite because he flinched in response. He didn’t complain or redirect her and it was an entertaining dynamic between them.
I decided that while he was distracted by his wife, I would slip his cock into my mouth. He lifted up his hips to help push himself all the way into my wide opened warm mouth. I loved the heft of his cock filling up the space and reaching the back of my throat. He tasted fresh and delicious and I was happy to devour him. Sally noted my move and came to hold my head in place while Joe thrust himself repeatedly into my mouth. There was something stimulating about having a woman control the action. It seemed as though it was exciting for all three of us.
Sally let go of my head while I continued to suck her husband. She came around to the backside of my bent over body and gave each of my bare ass cheeks a firm slap which I was certain produced at least a pink color. The smacks sent a pain signal straight to my brain. I just focused on the wonderful cock that was in my mouth. I was willing to take some pain given all of the pleasure that I knew was coming.
I reached under Joe and used my oiled finger to stimulate his anal opening. I was convinced that even though he was a strong man with a big dick, what he really wanted was to be bent over. At first, Joe didn’t respond to my finger rotating and massaging his anus, but then he let himself go and relaxed into the sensation. I felt his cock get harder as I pressed to gain a little entry. He was very tight as I had expected. He was not my first anal virgin, so I knew that I needed to be patient and let him push himself onto my finger rather than the other way around.
Joe sensed what I wanted and began to move himself left and right on the finger until he got comfortable enough to push down on it. I felt the excitement happening in his body with this fantasy becoming a reality. He was being penetrated! Eventually, I was able to reach his prostate and give a firm press. I tasted some precum that released as a result. The sweet flavor encouraged me to rotate the finger on his G spot and give him sensations that were likely new for him. He began to moan and Sally went up and held his head while she nibbled on the side of his neck vampirishly. She was wearing a bright red lipstick which was quite appropriate for the actions. She pulled back and leaned her pendulous breasts into his face completely covering it. Now he was in bisexual heaven with beautiful breasts and penetration happening simultaneously. I thought that I might be able to make him orgasm in this position but he never got fully hard. I was confused by that but continued the process of stimulating the prostate while sucking on his cock.
I pulled back and directed Joe to come to the end of the bed and get into a doggy position. I asked Sally to lay back on the bed with her pussy in his face to distract him. I put on a condom and lubed up heavily while they got into position. His ass was fully exposed and I toyed with his mind by rubbing my hard, lubed cock up and down the ass crack. He began to wiggle his butt wanting more, but I knew that my cock was going to be painful for him. I lubed up his entry and slipped my middle finger inside. He was licking pussy voraciously and Sally had already cum on his face once. I loved being in any of these three positions, but I knew that my task today was to take Joe’s anal virginity.
I reached underneath and pulled Joe’s massive cock back toward me. I rubbed our two cocks together so that we both got really hard. I returned to rubbing his opening with the tip of my stiff cock. “Give it to me,” he spoke into Sally’s pussy. “This is gonna hurt,” I warned him as I pushed in just the head of my cock. I felt his body tighten from the pain and he squeezed tightly on the head of my shaft. I knew that firm squeeze was coming, so I was able to remain inside. “Just breathe through it,” I directed and he went back to focusing on his wife’s very wet pussy. I moved my cock back and forth sideways to help loosen up his hole and then I pushed in another inch. I waited for him to get comfortable with that amount before I pressed further and gave him another inch of thick dick. He was learning to accept his position and said heavily, “I’m OK.”
What Joe didn’t know was that I was only half way in at that point. I remained patient and moved deeper one inch at a time continuing to use the sideways movements to expand what his ass could take. Having his wife’s pussy for focus was great because she nurtured him by saying, “You can do it. Just relax and be a good pussy boy. You know you want to be fucked by a real man.”
I decided not to push my hard dick all the way in, but to slowly move back and forth giving Joe time to feel the new sensations of actually being fucked by a real cock. He may have had toys before, but I could tell that this was new territory for him and he wanted it. Joe was ready to be on the receiving end of a good hard cock. After sliding back and forth, in and out of him for five minutes, I decided that that was enough for a first day removing my dick from his tight ass. I slid off the condom and pressed myself against his naked cheeks. I stroked my firm shaft until a big load of cum squirted onto him, marking my new territory. “That was really hot,” he confirmed from his subservient position.
I pushed Joe over onto his back so that his cock was fully exposed. He was no longer hard which was not uncommon after being fucked. There was some oil on his cock from when I was stroking it and that made it easier to take deep into my throat. He relaxed his body and let me take control. Sally leaned over and twisted his nipples firmly while pushing her voluptuous breasts into his face. I sucked him deeply and with passion while I massaged his balls. He got harder but then returned to his original state. I persisted and pushed a finger up his freshly fucked ass. That created some stiffness but then he lost his erection completely.
“I don’t think it’s going to happen,” he finally declared with a sigh. I understood and said, “I’m sometimes that way myself. I lose interest in my own orgasm if I’ve been penetrated.” Sally kissed him sweetly on the lips saying, “I have to clean up a bit.” That may have been true, but I think she also wanted to leave just the two of us together.
“Are you OK?” I asked and he said, “Part of it is that I can’t come with a guy if she’s there. I don’t exactly understand it, but that seems to be how it works for me.” “Yes, but that’s your deal with her. She’s to be with you for man on man sex,” I reminded him. “I can’t let myself go completely when she’s watching. I get self-conscious and I stop being hard. It’s very frustrating,” he continued emotionally. At that point Sally returned with a bubbly attitude and the atmosphere and conversation changed.
“So there. Now you’ve been fucked,” she said with satisfaction. “Now you know how I feel when your big cock slides inside of me. And I love it,” she said with a genuine loving smile. “It really hurt in the beginning, but then I kinda got used to it and it felt good.” I chose to let the conversation with Joe stay between just us and complimented, “You did great for your first time. Like a champion!”
Joe decided to go to the bathroom and Sally came over kissing me sweetly on the lips. “Thank you for being gentle with him. It was really hot to watch you fuck him. I didn’t know I would like it so much but it got me so excited!” “Yes, I could tell by how wet the towel got,” I joked with her. She pressed her naked body firmly up against my naked body and gave me another of those deep passionate kisses. Her red lips pressed against mine and she pushed her tongue deep inside me. I was surprised again by the level of intimacy which was so unusual in a married woman. Was she feeling more than was good for her marriage? Was she just being a bad girl which she hadn’t had an opportunity to be before? Was she testing her own limits?
Joe returned and the energy moved into putting clothes back on. “The massage was also really great,” offered Joe as he shook my hand firmly at the door. Sally gave me a quick kiss on the lips and a smack on the ass. “Thanks for a great time. See you again soon,” were the last words I heard her speak.
Afterword
Sally’s final spoken words to me turned out to be not very accurate. I never did see them again although we kept in touch. We hadn’t set up a third meeting date and when I asked about that in emails, Sally informed me that Joe’s work was keeping him too busy to be able to play. I certainly understood work issues and my own changed as well. A month later, I was called back to my New York office for another position and didn’t return to Chicago.
I kept in touch with Sally who told me that they had found a younger regular man who they were playing with. He was really hot and Sally was having tons of great orgasms with him. She also informed me that they had met a male/female couple who were both bisexual. The other woman enticed Sally to play with her while the men were playing and Sally, to her surprise, discovered that it was exciting being with a woman. Something that she had never considered. I was happy to hear that Sally was coming into her own sexual discoveries. Once open to the idea, there were many people who became more flexible about their sexual interests than they had envisioned.
In later emails Sally described how she was becoming much more dominant with men and with women and that it encouraged a part of her sexuality that she hadn’t felt before. She had even bought some paddles and whips as well as light restraints. Her former sex life had been very satisfying, but this new world had a range of options that spoke to her own curiosity.
About a year later, I was checking in on Sally, when she alerted me that her world was falling apart. The relationship with the extra man had ended and Joe was not happy about Sally’s new bisexuality. He didn’t want her to be with women. Apparently, he had a double standard where it was OK for him to be bisexual but not OK for her. She understood that he was threatened by this turn of events, but she refused to allow him that double standard. Sally and I had many long emails discussing her new challenges and I provided her a much needed outlet for support. There wasn’t really anyone else for her to turn to who understood as much as I did. Their sexual life was hidden from the people that she knew in Chicago. Sally was grateful for my supportive listening and empathy.
In standing her ground, however, it made Joe angry and he became resentful and distant. He started spending time with men without her. This was very disturbing, but she decided to fight fire with fire and chose to play with couples without him. This escalation didn’t go well for either of them in their relationship. They had arguments which hadn’t happened much in their long marriage. Neither was willing to concede ground and so a stalemate was achieved with unhappy dissatisfaction on both sides.
I didn’t communicate with Joe so my information was one sided, but Sally was always level headed and there wasn’t anything she told me about Joe that was inconsistent with what I had learned about him during our naked times together. I had felt the anger inside him and knew that wasn’t willing to be open about everything. His double standard took me by surprise, but that was due to my sense that bisexual people were more likely to be understanding about other bisexuals. I was proved wrong in this case.
I empathized with Sally’s frustration about her husband’s double standard and encouraged her to be as open and understanding as she could be in hopes that he would eventually accept that she had new needs that were only there because he had initiated a more open sexual relationship. A great deal of trust was required to let the person you love have sex with another. Significant personal strength was necessary to be comfortable when you watched your partner with someone of the same gender. It seemed like Joe was threatened and felt that he couldn’t compete equally.
I kept in touch with Sally over the years and learned that she remained married to Joe. There was some improvement over time as they both got used to the new normal which included periodic arguments. Their children were likely to have seen some emotional changes between them, but would have had no insight into the real causes of the changes. The truth of many marriages was hidden from the children, especially once they left the nest.