Mary Sue and I were living in her two-bedroom condo. The condo was huge. Her parents furnished it with Leathercraft’s full-grain leather furniture. We had a couch, a loveseat, and a couple of chairs. I don’t know if they choose leather because it’s easy to clean up body fluids, but it is. Both bedrooms had king-size beds. They also furnished the condo with everything else needed to live comfortably. The parents also bought a 50-inch plasma TV. The picture’s quality was gob-smacking. Bob told me the retail price was over $10,000. We also had a CD player to play movies. The living room was a real gathering center when Mary Beth or I weren’t fucking.
I again got straight ‘A’s in the first semester of my sophomore year. When I received a congratulatory letter informing me that I had made the President’s List, it also announced that I had been awarded a scholarship to cover my tuition for the next semester. Tina and Ned (Andi’s Parents) were thrilled that I was lowering my college costs. I was amazed at how much biology has advanced since I was in school 30-some years ago, in another life.
Maria (Andy’s wife) was still struggling with loneliness. I felt guilty that I had left her, but not by choice. I was able to keep my school schedule clear on Friday morning. Even as lonely as she was, she actually seemed to be hornier than ever. She had settled on sex with the clone Willy dildo used as a strap-on. She commented more than once that she really liked how I pumped her with it. I was able to wear the strap-on low enough that it pressed against my clit. I couldn’t get an orgasm this way, but it sure gave my clit a huge hard-on. After she brought me off, we would collapse in each other’s arms and sleep through the night. I told Maria she needed to find a steady boyfriend to stay with her through the nights. I even suggested a steady girlfriend. She seemed to be more receptive to the idea of a girlfriend.
This marked the start of an interesting chapter in my life. Donna (Mary Sue’s mother) basically pimped for me. She hooked me up with some of the movers and shakers in our area. Donna told me she asked them to pay me whatever they thought the experience was worth. It was amazing how much money I was given for a night of fun. Rich businessmen and politicians almost always have a high sex drive. They tend to be slim, and their wives are usually very pretty. I was surprised they never objected to an STD test. I was diligent in checking the STD test paperwork before I ever took a piece of clothing off.
Once we got the paperwork done, I would sit down with the couple and talk about their sexual likes and dislikes. It was much easier for the couples to admit what they didn’t like than what they liked. I always avoided everything they didn’t like and felt everything they liked, and more was fair game.
With Donna’s help, I recognized several people I knew in another life. And one had been an actual client of mine when I was Andy. It really excited me to meet up with well-known couples in the area who were surprisingly kinky. Every wife was turned on by our encounter and was very bisexual. The husbands were also sexually excited, and it took no time at all to make them cum. What a great part-time job. I got fucked, usually to orgasm, and got to make love to beautiful women. The first time, they would hand me 10 $100 bills. I suspect that amount was Donna’s doing. I told Donna to have them pay me what they wanted to. The $1,000 was most likely her ‘suggestion’. After the first “session”, the amount would vary, but would always be more than the first time.
After my first $1,000 pay day, I drove over to the Hustler Store in Monroe, Ohio. I bought a variety of sex toys and lingerie. Dildo sizes to fit all pussies and asses. I bought a carry-on suitcase to transport my sex equipment. After the first “meeting”, I got a feeling of what they really wanted. I would drive over to the Hustler Store and buy it. Taste would vary greatly. Some women wanted smallish dildos, while others wanted dildos that really stretched them. When I bought strap-ons, I assumed it would only be for the wife. More than once, I fucked the husband in the ass with a huge strap-on. And when it came to lingerie, there was no telling. Some of the most sophisticated couples wanted me to wear the tackiest I had. Other couples just wanted me naked.
It got so crazy that Donna kept an appointment calendar because all “dates” went through her. She would send me an email reminding me of the address. Donna told Mary Sue that she was to share her car with me when I needed it, and at certain times, I had priority no matter what. Mary Sue was fine with this. I had told Mary Sue about my little sideline business.
February 19th, 2001
February 19th, 2001, fell on a Monday. It was also Presidents’ Day. A lot has happened in the 6 months since I last wrote. There was no school because of the holiday. It meant an extra day for fun and fucking. Donna had called late last week and asked me if I could fit in another couple today, even though I had pretty much stuck to only one couple a month. She said it would be “worth my while”. Donna claimed the couple was well known in Cincinnati. I asked Donna if she knew what they were into. She said, “The husband’s a watcher.” As strange as this sounds, the husband wanted to watch the wife get fucked, but not by a man. I referred to men like that as cuckold light.
Today turned out to be very busy. That’s why I wrote about it. I had a “meeting” with a well-known couple in Cincinnati. Mary Sue was bugging me to hook her up with a guy who had a bigger dick than Bob. “Andi, I really think I would like to try a guy with a bigger dick and taste somebody else’s cum.”
I told her, “The smallest dick guy I know is Bill. I think his length and thickness may be a little too much for you.”
“He sounds perfect.”
“Mary Sue, if you’re going to fuck him, you’ll have to seduce him. “I’m willing to talk you up, but you’ll have to convince him he should fuck you. Bill has a huge dick compared to Bob. I really think you’ll struggle fucking him.”
“I certainly hope so. I’m getting bored with my small dick guy, and he isn’t very smart.”
“I thought you were sweet on Bob?”
“He was fine for a while, but I’m ready to move on.”
I told her, “I’ll see if I can get Bill over here at 7:30.”
“That may be a problem. Bob said he wanted to see me then.”
“Mary Sue, I’ll get Bill here at 7:00, and when Bob shows up, I’ll take care of him. I have something I want to try with Bob.”
“What’s that?”
“I’ll tell you if I can get him to do what I want.”
We left it at that. I called, “Bill, Andi here. Today is a holiday, and I wondered if you would like to get in another fuck?
“Andi, you know I can’t turn down fucking you.”
“Here’s the deal, Bill, it’s not me who wants to fuck you today. It’s my cute roommate, Mary Sue. She has only fucked one guy in her life, and he has a really small dick. She wants to try something bigger. You’ll have to go easy with her, or you could really hurt her with that huge dick of yours. She doesn’t know that you have agreed to fuck her. Make her work for it. One last thing, unlike me, Mary Sue loves to give blow jobs and actually likes swallowing cum.”
“I’ll be there at 7 sharp,” I told Mary Sue, and that Bill would be here at 7 to fuck me unless she could convince him otherwise. I told her I would help with the seduction.
Early in the afternoon, I drove to a mansion in Indian Hills. For those who don’t know, Indian Hills is where the uber-rich live in Cincinnati. They must have been waiting, because they greeted me at the door even before I rang the doorbell. The temperature was around 50. I was a little cold. I was wearing a knitted halter top, tied in the front. The top really accented my boobs, and my nipples stuck out farther than normal. As usual, I was wearing a very short tennis skirt with my go-to bare cunt panties.
The wife was standing in front of the husband. I immediately recognized them as Nick and Cheryl from Cincinnati TV. Cheryl was a national beauty queen. Nick was a local TV personality and a jack-of-all-trades. Today, the only personalities you have locally are news, weather, and sports. She was truly a raven-haired beauty. Her hair was long and curly. She had steel blue eyes that could look right through you. The couple was wearing very conservative robes.
I said, “My god, you are beautiful.” She scrunched up her face as if she heard this every day of her life. She said, “Come in quickly; you’ll freeze to death dressed like that out there.” It was cool, but not that cold. “Let me show you to our bedroom.”
I said. “First, we have some business. Do you have the results of your STD tests?”
“Of course. These are mine and my husband’s.”
She handed me the medical test results. “Do we pay you now?”
“Not until we’re done.”
“You’re very trusting,” Nick finally spoke.
“I am going to pleasure you so much; you’ll feel like you got a good deal.”
As they led me into their huge bedroom, Nick caught me from behind, grabbed my boobs, and started to hump me. “Slow down. I thought you wanted me to do your wife.” I was always cautious with my language during the first meeting.
“I do want my wife fucked by you, but I couldn’t resist grabbing those tits of yours.”
“You need to make some choices.” I opened my suitcase (I started taking so many items I needed that I needed a large suitcase) and said, “What would you like me to wear?” It’s interesting that the husband decided what I should wear. It was a black bustier that fully exposed my boobs. It had suspenders for the seamed black hose he picked out. And he wanted me without panties.
I then turned to Cheryl and said, “What size strap-on do you feel comfortable with?” She picked a rather smallish strap-on. “I have found most women will enjoy a strap-on bigger than they think they can take.” With that, she picked the largest one I had. I think she wanted the huge one, but didn’t want to say it in front of her husband.
“I’ll be in the bathroom getting ready. You guys should too.” I noticed in the bathroom that I was really turned on. Close up, I couldn’t believe how beautiful Cheryl was. My clit was rock hard thinking about seeing her naked. As Andy, I could never have believed I would be this close to what might be the most beautiful woman I had ever seen. I opened the door and said, “Are you guys ready?”
“We are”, Cheryl yelled back. As I walked out into the bedroom, there was the wife on the bed with her robe still on. Nick was naked in a chair with his erect dick in his hand. I quickly realized the couple had never done anything like this. I needed to go slow. I lay next to Cheryl and said, “Can I open your robe?”
“Please.” I leaned over and whispered in her ear, “We’ll take it slow. Let me know if this is something you feel uncomfortable with.” I slowly unfastened her robe and just pulled it open. She was totally naked under the robe. I have never seen a body like that. It was obvious her large, beautiful boobs were all natural. Natural boobs lie to the side when the woman is on her back, just like hers. Really odd was that her nipples weren’t erect. It told me she really wasn’t into this. Her stomach was actually slightly concave, and her pubic mound was covered with thick, jet-black pubic hair that shone. The carpet matched the drapes. She didn’t even shave. I couldn’t even see any of her vulva; her thick hair covered everything.
“Can I kiss your nipples?”
“I’d rather you didn’t.” I took this as a no. I slowly started to kiss her breasts, avoiding her nipples. Slowly, her nipples started to harden. I brushed my lips against her newly erect nipples. I heard a slight sigh. I slowly kissed my way down her chest, stomach, and pubic mound. I noticed her hips were slowly moving to meet my kisses. Slowly, I spread her legs. I could smell the strawberry cleanser she used on her pubic hair. I worked my way down to her clit. I barely touched it with my tongue, and she jerked. I slowly continued my very light tongue play.
I really hate going down on a woman with pubic hair. Shaved cunts are so much nicer. As I tried to insert a finger up her, I realized she was very dry. I had placed my tube of lube on the bed just in case. I dripped the lube on my fingers. With that, I went back to tonguing her clit as I slid two fingers up her vagina. I heard a slight gasp, and her hips started to move to the rhythm of my fingers. Her pussy was fairly tight. I thought she would struggle with the large strap-on.
I said in a whisper, “Are you ready for me to fuck you?”
“Please, now.”
I put on the large strap-on and really lubed it up. I pulled her by the legs to the edge of the bed. I had started to bring the Magic Wand with me. If I used it, I would leave it with the woman. I used the Magic Wand because sex educator Betty Dodson had taught thousands of women to cum with it. It seemed like the go-to tool to help women who had trouble orgasming. I turned the Wand on low speed (the original model only had two speeds). I handed it to Cheryl and said, “Put this on your clit. If it’s too strong, put it to the side of your clit.”
As I slowly inserted the strap-on, I kept dripping lube on the shaft. I looked at her face and saw her grimace. I said, “Is this too much?”
“No, keep going, but slowly.”
As I got the strap-on about as far as I thought I should, I said, “Tell me when it’s deep enough.”
She said, “Deeper.”
Again, I pushed it in a little farther. As I watched her face, her grimace changed to a more relaxed look. “That’s it, right there.”
I told her, “You need to move on anything that feels really good.”
Slowly at first, she ground down on the strap on. Her mouth opened, and she started making low throat sounds. It was obvious Cheryl was starting to enjoy being fucked. I asked her if she wanted the vibrator to be stronger. She shook her head, yes. I flipped the speed switch to high. She started to gyrate her hips to match my thrusts with the strap on. As she increased the speed of her hips, so did the sounds she was making. This went on for several minutes. All this time, her husband was sitting in a chair, stroking his cock. He was really into his wife getting fucked.
Cheryl was having trouble getting over the hump. I was pretty sure she had never had an orgasm. Between 10 and 15% of women in the US have never orgasmed. If I could get her off, it would become easier and easier for her to orgasm. If I were a man fucking such a beautiful woman, I would have cum long before her. This may have been one of the reasons she had never orgasmed.
It was obvious Cheryl was going to orgasm if I could just keep up what we were doing. She became louder and louder. And just like that, she said, “Oh my god,” over and over. As I sped up my strokes, she matched them. I kept stroking long after she came. I know how sensitive a vagina can be, even after orgasm. As I was pulling out the strap-on, it looked like a small river of liquid coming out of her pussy. The same woman who had a very dry pussy, was now soaked.
After Cheryl recovered, she looked up at me shyly and said, “Thank you.’
“Was that your first orgasm?”
“It was. How did you know?”
“Just a lucky guess.” The truth was, it was obvious. She was hard to make cum. “The good news is that after your first, it gets easier and easier. I want you to keep the Magic Wand. It will help you orgasm.”
Cheryl was very appreciative. The truth was, if I used a Magic Wand on someone, I gave it to them. I bought them six at a time and got a great deal.
Nick had finally finished in a Kleenex. He stood up and said, “I think we’re done here. And with that, he walked into the bathroom, Cheryl in tow. I took my outfit off and put back on the clothes I came in. My pussy was soaked, and I was very sexually excited. Normally, when I met with a couple, I would be guaranteed at least a couple of orgasms. The only thing I got was a burning desire to fuck.
I could hear raised voices in the bathroom. Eventually, they came out wearing the same robes they had gone in with. The husband looked at me and said, “You can go?”
Cheryl broke in, “Honey, we forgot to pay her.”
Nick gave her a dirty look, walked over to a wallet on the dresser, and took out 10 crisp, new $ 100 bills.
He said, “You can show yourself out.”
The wife standing in front of the husband mouthed the words, “Thank you.”
I told them, “If you want to do this again, just call Donna.” I never heard from them until much later, but what happened afterward was very interesting. Donna had had several women, friends of the wife, request my services. For the most part, they were good-looking, thin women who had never cum. In most cases, the husband wasn’t present. My bet was that the husbands weren’t there because they didn’t know the wives had hired me.
As I was leaving, I had no idea that Cheryl would be involved in the loss of one of the great loves of my life.
As I got into Mary Sue’s car, I felt the session with the couple was bittersweet. I was bitter about how I was treated. I was treated no more than an object and not as a person. The sweet part was that I had made love to what was maybe the most beautiful woman I would ever see. Over the years, I have found that some very beautiful women are even more beautiful in person than in pictures.
As I drove out of their long driveway, the bitter was no longer on my mind, and the sweet made me more and more turned on. By the time I was on the entrance ramp for I-275, I was teasing my clit through my thin, wet panties. I knew if I got an orgasm, I would probably crash Mary Sue’s car. Today, what I did is called edging. I’m driving at 70 mph, playing with my clit and bringing myself right to the brink of an orgasm, but not over. I still get turned on thinking about this.
I exited onto US-27 north, onto a four-lane highway that quickly narrows to two lanes. I got stuck behind an old man driving at least 10 mph below the speed limit. This caused me to increase my edging so that I must have brought myself to the edge at least 10 times. As I pulled into the parking lot at the condo complex, I ran from the car to our condo. It reminded me of times I ran to use the toilet, but it wasn’t the toilet I needed.
Mary Beth was in the living room watching TV. She wanted to talk about tonight. I ran past her and yelled, “Later.” As I closed my bedroom door, I tore off my soaked panties, grabbed my dildo from my dresser drawer, and rammed it up my throbbing cunt while I was still standing. Mary Sue startled me when she came into my room, walked me to my bed, and told me to lie down. She asked, “Can I help?”
“Grab the dildo and really pump it hard.” With that, I came with more to come. She knelt at my side and started to suck my clit. She had learned to give great head from all the blow jobs she gave Bob. She pounded the dildo on my cervix, sending me into world-class orgasms. I had been teasing myself for about an hour and was greatly rewarded for the wait. I was afraid I might hurt Mary Sue with my pubic bone from the bucking of my hips. I really thought I might stroke out from the last orgasm.
After I was done, Mary Sue said, “What the hell was that about?”
“I met with a couple to fuck the wife. She was the most beautiful woman I had ever seen. I finally got her off, and that was it. I only got turned on, but no orgasm. Coming home, I teased my clit the entire trip. I barely made it to my room. By the way, it’s a good thing you have leather seats in your car. I think I soaked them.”
“Andi, are you going to be ready tonight?”
“I think you know me well enough to know it doesn’t take long for me to reload.”
“Does Bill have that big of a cock?”
He’s no Jimmy, but he will shock you with his size. You have to remember, he has taken Viagra and fucking you for the first time. He will be rock-hard and maybe a little bigger than usual. You have to be careful, or he could really physically damage you. Don’t try to ride him like you do Bob. Your best position for the first time you fuck a huge cock is doggy style. You can stroke your clit to ease any pain. And don’t forget the lube.”
Andi, “I’m so wet right now, I don’t think I need any.”
Don’t kid yourself; anything to help that mammoth cock get up, you have to help. Believe me.”
“So how are we going to do this with Bill and Bob?”
“If I know guys, when pussy is involved, they’re going to be early. I have already told Bill you were interested in his huge cock. I will greet Bill, sit down with him in the living room, and you come in and act like you might be interested in a big dick fuck.”
“Andi, that sounds kind of stupid.”
“What do you have in mind?”
“I thought I would pass through the living room to the kitchen. I’ll be wearing something sexy. I’ll make some chit-chat and go from there.”
“OK, if you can get Bill into your bedroom, I’ll take care of Bob when he shows up.”
“What do you have in mind for Bob?”
“We’ll see.”
The doorbell finally rang just a little before 7. I was wearing a loose-fitting top with no bra. I was wearing my go-to tennis skirt without panties. I was glad Mary Sue’s parents bought leather furniture. Easy to clean anything left from my wet pussy. Bill gave me a hug at the door, grabbing one of my ass cheeks. He asked, “No panties?”
“I thought I’d get you ready for Mary Sue. You need to take it easy with her. She had only fucked one guy, and his dick wasn’t much bigger than my clit.”
“I’ll be gentle.” Bill and I sat down on the couch. In just a minute or two, Mary Sue came strolling by in one of her beautiful custom bras and a very small thong. Bill said, “My God, you look absolutely beautiful.”
Mary Sue actually said, “All the better to fuck.” I couldn’t believe she actually said that. She continued, “I understand you’re well hung.”
Bill responded, “I can assure you it’s not hung.”
She said, “Show me.” With this, Mary Sue pulled down Bill’s shorts and out popped a very impressive hard-on. Mary Beth turned to me with a smile and mouthed, “Wow.” Mary Beth dropped to her knees and started to lick the precum on Bill’s dick. She must have been practicing because she looked Bill directly in the eyes and started to deep throat Bill’s erection. I have no idea how she could get that dick down her throat without gagging. “Let’s go to my bedroom and finish you off.” Bill got up with his huge erection, pointing the way. Mary Sue turned her back on Bill and had him take off her bra and thong before they even got to the bedroom.
For the next 20 minutes, I listened to Bill fuck Mary Beth. She had no problem taking his dick. She started to make rhythmic grunting sounds. Mary Sue got louder and faster with her grunts punctuated by “Oh my god,” and right before she went silent, she yelled, “Don’t stop.” I had heard Mary Sue fuck Bill dozens of times, but I never heard her say “Oh my god” or “Don’t stop”. She repeated this cycle three times. I thought I was listening to a porno movie. What a turn on. After a couple of minutes, I could tell Bill was coming from Mary Sue sucking his dick.
A couple of minutes later, the doorbell rang. I was sure it was Bob. I knocked on Mary Sue’s door and said, “Are you done? Bob’s here.”
She answered, “For now. I think we may go another round.”
If you can wait five minutes or so, I’ll take care of Bob.”
When I opened the door, there was Bob smiling and all. “Is Mary Sue in?”
“Bob, I think she is busy with another project. Why don’t you come in and sit down?” For the next several minutes, I tried to distract him. I finally decided to be very direct:”Bob, why don’t you come into my bedroom and maybe we can try something neither of us has ever done?”
“What would that be?”
“Have you ever thought about anal intercourse?”
“You mean fucking you in the ass? Mary Beth and I have several times.” Wow, that was surprising.
“Have you taken Viagra?”
“Of course.”
I lay a towel on the edge of my bed. Grabbing my favorite dildo, I positioned myself on the very edge. I dripped lube on my pussy, feeling it run down to my asshole. “Bob, really lube up your cock. Now slowly push it into my ass. I am going to match your stroke with a dildo in my pussy. This should really feel good. Go slowly until I tell you otherwise.” Bob slowly entered me. I had been using butt plugs for a while and had had double penetration with my pussy; Bob’s dick actually felt good, but I had never had anybody move inside my ass. I inserted the dildo in my pussy. I matched Bob’s stroke. From his face, I could tell he was really enjoying himself.
I orgasmed several times, but nothing too intense. I felt I could get used to anal sex, but why? The one part I hated was having someone come in my ass. Cum and lubricants gave me loose bowels. Give me a hard dick up my cunt, and I am one happy gal.
As I was cleaning up, Mary Sue started up again. Bob said, “I thought you told me Mary Sue wasn’t here.”
“No, I said she was busy with another project.” With that, Bob, buck naked, bolted out of the room, opened Mary Sue’s door, and there she was on all fours, fucking Bill. She turned toward Bob and said, “Please close the door on your way out.” As the door closed, Mary Sue hadn’t missed a stroke. I have seen some really crazy things in my two lives, but that might be the craziest.
That was the last time Mary Sue spoke to Bob. It also started a relationship that led to marriage, two kids, and Bill becoming the CEO of the company owned by Mary Sue’s dad. I felt really good about hooking them up.
I was on the couch when Bill finally left. Mary Sue walked him to the front door in only a robe. Mary Beth gave Bill a very passionate kiss and said, “How about Friday?” She opened her robe and drew Bill’s mouth to one of her nipples.
I could tell Bill was thrilled and shook his head yes as he grabbed her ass. Mary Sue went to her room and came back with a towel. She arranged the towel on the couch and sat down on it. She turned to me and said, “My pussy is on fire.”
“I heard.”
No, I mean it burns. I really overdid it with Bill tonight. I should have stopped after the first round, but it just felt so good. Bill’s dick really stretched me, but the pleasure really masked the pain. Do you have anything to help with this?
“I’m pretty sure it’s not any kind of infection, just irritation. I told you to use lube. Take a couple of ibuprofen to take the edge off the pain, and I think I have some Tucks Pads. Use the pad on your vaginal lips and opening. It should soothe the burning. You need to slow down with Bill. Fuck him once for the next few weeks. I’m sure he wouldn’t mind if you deep throat him.”
Mary Beth took my advice and went slow fucking Bill. Within a month, she was fucking Bill as much as she did Bob. She told me the only thing she felt was pleasure.
Later that night, Donna called. “What the hell happened with that couple from Indian Hills?”
“I don’t think the husband was too happy.”
“You must have done something right for the wife. I have had several requests for your services from women who said they were her friends.”
“She had never orgasmed before, and it was a lot of work with very little pleasure for me. And I think the husband wasn’t really happy. If I’m going to help women get it off, I don’t want the husband there. Maybe I should ask for $2,000 for a woman by themselves. What do you think?”
“Let’s try that. It might cut down on just women.”
You’re probably thinking doubling the amount for my “service” would cut down on clients. Surprisingly, clients increased significantly. I have some great stories about servicing non-orgasmic women, but more about that later.