A lot has happened since I last wrote 4 1/2 months ago.
Ned still slipped me money anytime he could. I had accumulated even more money. As a family, Ned and Tina have taken care of all my needs. They contacted Mary Sue’s parents about some kind of payment for the condo where Mary Sue and I were going to live. Her parents said no money was necessary; they were just so glad Mary Sue found such a good roommate.
Our daughter, in another life, Abby, decided to stay in Columbus for the summer. She and her boyfriend got a job at a local brewery. In Ohio, you only have to be 19 to work in a brewery. Her boyfriend had a real interest in becoming a brewer after college. We were alone and didn’t have to explain what was going on. Maria was experiencing empty-nest syndrome. I was spending two to three nights a week at her house. We were only having sex about once a week, and the other nights we would kiss and hold each other through the night. I told Maria she needed to find a steady boyfriend to stay with her through the nights.
I again got straight ‘As’ in the second semester. When I received a congratulatory letter informing me I had made the President’s List, it also announced that I had been awarded a scholarship covering my tuition for the next semester. Tina and Ned were thrilled that I was lowering my college costs.
The last Saturday of the school year, I tried to talk to the beautiful woman who liked getting me off orally. She just goes down on me like a hungry dog with a bone, but wouldn’t even speak.
Mary Sue was becoming increasingly sexually active with Bob, if that was possible. This was the same girl who would blush if you mentioned sex. She now wanted to tell me a blow-by-blow (no pun intended) description of everything she and Bob were doing. This was also the same girl who would use words like thing, vagina, and breast, but now was using the same words I used. I felt a little bad about how I corrupted her, but felt great about how much pleasure she was getting.
I had double penetration with Bill and Tom two more times before the end of the school year. I actually masturbated more than once, thinking about this.
Jimmy called me at the start of July. He told me he had found someone else and planned to stay in St. Louis after he finished diesel mechanic school. His new girlfriend was an older woman with two children. I had only seen Jimmy a couple of times in the past year. I’ll miss his anaconda.
August 19th, 2000
August 19th, 2000, fell on a Saturday. The day before was the last day working at the pool supply store for the year. Working with Bob, I realized he was smitten with Mary Sue. I don’t know if he really cared for her or if it was all the fucking they did. I don’t think it mattered to Mary Sue; I just knew that sooner or later, she was going to break Bob’s heart.
I got up at 10. It was probably the latest I had gotten up since Christmas break. After getting a lazy breakfast, I got a call from Mary Sue. “Andi, can you come over in the next 15 minutes? I have something I am dying to show you.”
“Can it wait, Mary Sue? I just got up.”
“I can wait, but I’m not sure Bob can wait.”
That really piqued my curiosity. “I’ll be over as soon as I can.”
When I arrived at Mary Sue’s house, her mother, Donna, greeted me. She was a classic beauty. She wasn’t much taller than Mary Sue, with a similar body, except for her boobs. She was built like the proverbial brick shithouse. I was surprised that Mary Sue didn’t get some of her mom’s boobs. I learned later that she had had a boob job. Donna was wearing clothes that I thought were inappropriate for a 40-something woman. She was braless, and her top was a crisscross white halter with the front opening showing not just her cleavage, but a hint of areola, and actually showing the bottom of her boobs. That which wasn’t visible could be clearly seen through the thin fabric. Donna had less sag of her boobs than you would expect for a woman her age. She was also wearing hot pants. They were so high you could see the bottom curve of her ass and a great camel toe. I was sure she had nothing on underneath the hot pants. It was the same ass that Mary Sue had.
All of Donna’s behaviors struck me as strange. She squeezed me while we hugged. I could really feel her huge boobs against me, like I’m sure she felt mine. She then grabbed the hem of my tennis skirt and flipped it up. I was glad I was wearing panties. Before I could say a thing, she said, “I really want to thank you for helping Mary Sue come out of her shell. She has been painfully shy her entire life. I never thought she would ever go out on a date, let alone lose her virginity.”
I might be the only person thanked by a mother for helping her daughter lose her virginity. I said, “Did Mary Sue tell you that? With that, she reached under my skirt and grabbed my clit and gave it a yank. Donna said, “Mary Sue tells me everything.”
She then said, “If you’d like, why don’t you stop over later and maybe we could have some fun?”
When I was Andy, I didn’t run in the same circles as Donna or her husband, but I heard stories about some of their parties, including group sex. I thought she might be pimping for her husband. “I’m not fucking your husband.”
“I don’t want you to fuck my husband. I thought we might enjoy each other.”
I could feel wetness in my pussy. This could be interesting. “I’ll let you know.”
With that, she said, “Mary Sue and Bob are waiting upstairs for you. She said, “Don’t bother knocking.”
I walked through Mary Sue’s bedroom door. She was straddling Bob. I immediately said, “I’m sorry.’
“Don’t go, Andi. We’re just humping while waiting for you. You and Jimmy put on a sex show for me, Bob, and I would like to reciprocate. Sit down in the chair and watch the show.”
Mary Sue surprised me. She was totally naked. This was the same person who wouldn’t show her body, with few exceptions, in our dorm room. Her breasts were a good A cup now, and her small nipples were rock hard. She had started to shave her pussy.
Once I was seated, she pivoted around, and she and Bob were in a 69 position. Mary Sue attacked Bob’s small dick. Bob was furiously licking Mary Sue’s pussy. She started to make rhythmic grunting sounds. They seemed to match Bob’s tongue. Mary Sue grew louder and faster until she went silent, and her body seemed to stiffen. She was having an orgasm. She collapsed on Bob.
Once Mary Sue recovered, she turned quickly, startling Bob. She reached under herself, grabbed Bob’s dick, and inserted it into her pussy. She slowly bounced on Bob, trying to get every inch of Bob’s dick up her. Soon she was bouncing up and down at a furious pace. She was making the same grunting sounds, but this time even louder. One final bounce and she went silent. Bob kept thrusting as well as he could with Mary Sue on top of him. Mary Sue’s eyes rolled back in her head. The French call an orgasm ‘la petite mort’, which translates to ‘little death’. Mary Sue looked like she had died.
Mary Sue soon came back to life and repeated what she had just done. I don’t think she could have bounced any faster. Again, she made very loud grunting sounds followed by another ‘la petite mort’. She was so loud, I was sure her mother, Donna, would hear her if Donna were anywhere in the house.
During this entire show, I was playing with my clit under my skirt. I could have easily orgasmed, but didn’t want to do anything that could distract them.
Once Mary Sue ‘recovered’, she jumped off Bob and turned her attention to Bob’s dick. She put the cockhead in her mouth and started to stroke the thin shaft. Bob came quickly. Mary Beth took the entire load, turned to me, and made sure I saw she swallowed all of his cum. She got up and came over to me, kissed me, tongue and all. I could taste Bob’s salty cum. I remember doing something similar to Mary Sue when Jimmy and I put on a sex show for her.
In less than 5 months, Mary Sue went from a shy virgin to a whore in the bedroom. She had seemed to lose all her inhibitions. I told Mary Sue and Bob how happy I was that they found each other.
When I came down the stairs, Donna was waiting for me. She said, “Wow, that must have been a great show. My husband says she sounds exactly like me when she cums.”
I gave her a big French kiss. She tasted her lips, and I said, “Bob said hello.” She grabbed the back of my head and stuck her tongue almost down my throat. Donna said, “I love the taste of cum. Have you thought about it?”
I was reluctant to get involved with my roommate’s parents, but I was horny and wanted to get laid. “What time do you want me?”
“8 PM would be perfect. Make sure you wear something inappropriate.” With that, Donna reached up under my skirt and grabbed my clit again, rubbing it for several seconds. She said, “Wow, you are turned on.”
I kept thinking, “What did Donna mean by ‘inappropriate ‘?” I went through my closet and drawers for something over-the-top. I decided to go all black. I put on a black lace shelf bra that lifted my boobs but exposed my nipples. I broke one of my cardinal rules; I wore a matching lace thong. I hate thongs, but they really made my ass look great. I had recently purchased a black, very tight, low-cut crop top. It was so low cut that it barely covered my nipples, and the bottom barely covered the bottom of my bra. My breasts spilled over the top. I had a pair of black hot pants that didn’t even cover my ass.
When I arrived at Donna’s, she was waiting for me at the front door. She was wearing a beautiful, full-length silk-printed kimono robe. It had to be custom-made to fit that well with her huge boobs. She said, “Are you ready for an unforgettable night?”
“I always am. I thought you said to wear something inappropriate?”
“You haven’t seen the whole package.”
She led me to the incredibly huge master bedroom. The first thing that caught my eye was the mirror tile ceiling. I always wanted to see what I looked like when someone was giving me an orgasm.
Donna had me sit on the king-size bed. She slowly took off her robe, and I actually gasped. She was wearing a lavender see-through corset with suspenders. Attached to the suspenders were lavender sheer seamed stockings. She had a lavender lace g-string that covered very little. Just above the g-string was a very colorful butterfly tattoo. As I looked up at her huge breasts, I noticed the corset was boned and pushed her boobs up. Her nipples were surprisingly small, about the same size as Mary Sue’s. They were topped with a barbell running through them, a dangling chain with large diamonds. I was pretty sure the diamonds were real.
Donna was truly a beautiful woman. I was very excited. “How should we do this?”
“We need to get you undressed. Mike, you want to help.” Mike was her husband, and this was not part of the deal. He walked out of the master bathroom totally naked. Mike’s cock was maybe a little longer than most, but his girth was impressive. He had a middle-aged dick. It was perpendicular to his body. If he were anything like me when I was a man in another life, as an adolescent, my erect dick literally touched my stomach when I was standing. As I aged, the angle slowly approached perpendicular.
“I told you I wasn’t going to fuck your husband.”
“Relax, Andi, I wouldn’t let you fuck him, even if you wanted to. Mike and I have an understanding. We only fuck each other. We’re all here to enjoy each other, but Mike’s not going to fuck you; he’s going to fuck me.” With that, Donna gave me a big wet kiss while trying to slide her hand down my top. My top was so tight that she was struggling. I removed my top. I was really turned on. My boobs really stuck out, and my nipples were really hard.
“You should get those nipples pierced. After I got mine pierced, they became super sensitive.”
“If my nipples got any more sensitive, I would have to wear nipple covers for fear I would cum from just rubbing against my top material.”
“Andi, I don’t think you can really have a nipple orgasm.”
“You’re wrong. I’ve had them.”
“Maybe I could do that for you tonight.”
“Donna, all orgasms are good, but I’ve had much stronger ones from my clit and some large object stuffed up my pussy.”
“Well then, let’s get this party started.” With that, she grabbed the back hems of my hot pants and pulled them off. I was still wearing my see-through thong. I looked down and noticed a huge bulge from my very hard clit. Donna went down on my clit through my thong material. It felt great, but it’s not what I wanted. I raised my hips and took off the thong. My clit was almost standing at attention.
Donna went down on me like she was sucking a small cock. This definitely wasn’t her first head job she had given. By now, Mike was standing over and said, “Let me have a turn.” Donna changed places with Mike, who furiously licked me, but not sucking.
I was so turned on, I came. “Stick something up me.” As I think back, I realize women are so much better at foreplay with another woman than with a man. I think there is a natural gentleness. Women do to you what they want to have done to them. This also brings up another point: I don’t know if it was because of me, but a lot of women whom I knew as Andi were either bisexual or at least bi-curious. When I was Andy, I had no idea.
Mike had large hands, and I thought a couple of fingers up my pussy would feel great. “Mike, stick a couple of your fingers up my cunt, and stroke the front of my vagina. Donna, go down on me again, just like you did before.”
Mike said, “My god, you have the wettest pussy I have ever seen.” I think most wives would be upset if they heard their husbands say that about another woman.
“All the easier for you to put your fingers up me.” It only took seconds for me to cum again and again.” I finally said, ” Let’s finish this off by giving me one more really good orgasm. Mike, take your fingers out of my pussy and suck on my nipple. No biting.”
Mike said, “I think we have something you might enjoy.” He went to the foot of the bed and opened a chest. The top was positioned so I couldn’t see the contents. He lifted out the top tray on the bed. I noticed the tray was divided into two parts. One part had various pieces of jewelry, and the other part had at least half a dozen dildos of various shapes and sizes. Mike finally found what he wanted. “You might find this nipple clip very stimulating.”
I said, “My nipples are very sensitive; don’t do anything that loses the moment.”
“These can be adjusted for pressure.” With that, he put the clip on my nipple and started to tighten it. “Say when.” He tightened more than I thought I could take. I guess if you go slowly, you can take more pressure than you think you can. Mike then started to suck on the other nipple. He put both of his large thumbs around the bottom of my boobs and brought his fingers around the top of my boobs. As he squeezed, I looked up at the mirrored ceiling. I thought my boobs might burst, but damn, it felt great.
I said, “Donna, very slowly lick my clit. OK, now slowly insert your entire hand up my pussy. Now stop licking my clit. Move your hand slowly at first and gradually speed it up. I’ll do the rest.” I had noticed that if I got an orgasm from penetration alone, it took longer than if I stimulated my clit during penetration, but the buildup was so much better, and many times my orgasms were more intense. Mike sucking on a nipple and squeezing my boobs, a nipple clip on the other nipple, Donna fisting me, really gave me intense pleasure, but what sent me over was looking at the ceiling mirror. There were my boobs looking like they were going to burst. Donna’s hand disappeared up my pussy. I have no idea how long I came, but both of them kept going until I told them to stop.
Donna looked at me and said, “Now it’s my turn to have some fun.” She knelt on the edge of the bed and moved her hip back. This position exposed her labia at the very top of the thighs. I could see the area glisten with moisture. Mike handed me a leather paddle. I said, “What do you want me to do this?”
Donna said, “Spank my ass, hard. My safe word is red, like the color I want my ass to be when you get done.”
I hit her high on her ass. She didn’t even flinch.
”Harder and lower.”
I obliged.
“Harder and lower.”
I hit her ass cheeks. Again, she didn’t flinch.
“Harder and lower.”
This time, I was really going to hit her. I played club tennis in another life. My wrist begins in a laid-back position and then accelerates forward, snapping into the spank just before contact. Donna let out a groan.
“I love the pain, but you have to spank lower.”
I told Donna, “If I spank you any lower, I’m going to be hitting your pussy.”
Shockingly, she said, “That’s what I want.”
I hit her across her upper thighs and pussy. Not as hard as the last time. Donna said, “Hit me as hard as you did before.”
I really hit her exactly where she wanted it. She recoiled, her hips rotated forward for a second, and then backward, still exposing her pussy.
“That’s more like it. Keep going until I say red. As I paddled her, she would let out a yelp of pain followed by a moan of pleasure.
I started by becoming concerned about the pain I was inflicting on Donna. She started to make rhythmic grunting sounds after every yelp. They seemed to match my paddle hits. Donna’s voice grew louder until she went silent, and her body seemed to stiffen. She was having an orgasm. I kept paddling her until she finally said, “red.” She collapsed on the bed. Her ass cheeks, upper thighs, and pussy were cherry red. It was at this point in my life that I realized the body could be trained to have an orgasm from almost anything. Donna’s build-up and orgasm were very similar to those of her daughter, Mary Sue. The one characteristic that they both had that I found strange was how their eyes rolled back in their heads. I always wondered if the orgasmic pattern of a woman was inherited from her mother. Years later, after I became a trained dominatrix, I realized I had no idea what I was doing and was lucky that I didn’t permanently damage Donna.
While I was paddling Donna, Mike had put a Magic Wand vibrator and a rather large dildo on the bed. By now, Donna was on her back with her ass on the edge of the bed.
Donna said, “Mike, you need to get over here and fuck me; I’m on fire.” I wasn’t sure what she meant by ‘on fire’. Mike was lubing up a butt plug. He put it up her anus. Mike grabbed Donna’s legs and pulled her to him, and almost immediately inserted his erect cock into Donna’s wet, ‘hot’ pussy.
Mike said, “Wow, your pussy is burning up.” He fucked her very fast, and from my angle, it looked like every stroke went to maximum depth. He was pulling on her nipple piercing hardware. For a minute, I thought he might actually tear a nipple. It didn’t take Donna long to orgasm with the same pattern I saw with her paddling orgasm. Mike gave out one long grunt and had obviously cum. As he pulled out his deflated cock, he also pulled out the butt plug.
While Mike was lubing up their rather large dildo, Donna had scooted back on the bed so her feet were now on it and her legs spread wide open. As Mike was slowly inserting the dildo, Donna grabbed the vibrator. Donna’s expression immediately changed. It went from slightly painful to very relaxed. When Mike put the dildo up as far as it would go, he slowly moved it in Donna’s cunt. He was going so much slower than when he was fucking her.
Donna grunted every time the dildo was all the way up her. Mike slowly increased the speed of the thrusts of the dildo. Each time it was all the way up, her grunts got a little louder. By now, Mike was stroking the dildo up Donna’s pussy about as fast as he had with his dick. All of a sudden, Donna went silent; her head strained back, her mouth opened, and her eyes rolled back in her head. Mike said, “Keep it on, keep it on, ride it out.”
As Donna lay there comatose, Mike kept pumping the dildo in Donna’s pussy. Eventually, Donna started to raise her hips to match the dildo’s stroke. Mike’s strokes became very strong. Donna started to grunt again, but this time it sounded like pain. She continued to match the dildo’s strokes. Donna followed the same pattern again as she got her fourth orgasm.
This entire time, I was sitting in a chair playing with my very hard clit. I didn’t orgasm, but I could have easily. When Donna finally recovered, she looked over at me and said, “Looks like somebody would like to go again.”
I said, “I think I could. Are you guys up for it?”
Mike looked at me, staring at my clit, “I hate to send somebody home this turned on. Andi, have you ever tried a butt plug?”
“I don’t want anything up my ass.”
Donna laughed. “I don’t think you understand what a plug can do for you. If you’re game, we’ll start with a really small one.”
Mike lubed up a small butt plug and handed it to Donna.
“Lie back on the bed. Put the vibrator on your clit as I insert the plug.”
I obliged. As Donna slowly inserted the plug, it actually felt good.
Donna said, “Don’t cum yet. The best is yet to come.”
With that, Mike handed her a large dildo. As she slowly inserted it into my pussy and said, “Feel the pleasure of the butt plug. Notice how the dildo fits so tight and is being pushed forward to your G spot by the plug.”
Mike climbed onto the bed and started to suck one of my huge, erect nipples, and started to pull on the other.
I looked up at the mirrored ceiling and had a series of orgasms that seemed more like convulsions. I have no idea how many orgasms or how long these lasted. I lost all sense of time.
The master bedroom had a huge walk-in shower, so of course, we all showered together. There is something about fondling a soapy body, especially boobs. Donna and Mike sandwiched me. Mike was behind me, fondling my soapy breasts, pulling on my rock-hard nipples. He had his semi-erect cock in the crack of my ass, slowly humping me. Donna had soaped up my pubic area and started to jack off my clit. That double team really turned me on again. I was actually happy that they stopped short of giving me an orgasm.
As we got out of the shower, I noticed Donna’s butterfly tattoo was fading. I asked, “Is your tattoo temporary?”
“Of course it is. I put it on for you. I would never get a permanent tattoo on my pubic area. It would eventually look like hell, and it would mean I would have to shave my pubic area all the time.”
Mike turned to me and said, “You have such an unusual body. I’ve seen lots of naked women, but your figure is spectacular; your clit and nipples are very unusual.”
I said, “Unusually good or bad?”
“Most definitely very good,” Mike responded.
“I like to think I have the body of a woman, but the mind of a man.
Donna looked at me and said, “How so?”
“I think I read somewhere that the average man thinks about sex 19 times a day. Women 10 times a day. I probably think about fucking 30 to 40 times a day. I’m a very horny man trapped in a beautiful woman’s body. As a woman, I can have multiple orgasms. Many multiple orgasms at one time.”
Donna said, “I think I fit in that description.”
“Donna, how many orgasms have you had at one time?”
“I don’t know. Maybe five or six.”
“I can have more than a dozen, and the only reason why I didn’t have any more is that I am exhausted, not because I was done. I have never been fucked to completion.”
Donna looked at me and said, “That could be great for the next time. If you want to next time?”
I noticed that Donna and Mike were talking in a low voice. Donna turned toward me and very seriously said, “Andi, we have some friends who are also into kinky sex. If you would be interested, I can hook you up.” I said, “Here’s my problem. I love dicks up me, but I hate rubbers. I have started to make it a personal policy that I will only fuck somebody who has had an STD test. If they are clean and don’t fuck anybody else after the test, I just might fuck them. If I agree, once a month is all I could spare. No rough stuff and no anal (the anal would change). I also need a car.” More about this later.
After all the “business” was out of the way, Mike blurted out, “Does that go for me, too?”
“Mike, are you talking about fucking me?” He nodded his head yes.
I turned to Donna and said, “I thought you said Mike doesn’t fuck anybody but you?”
“I can tell Mike is so taken with your ‘unusual body’ I might have to revise that rule.”
I went over to the small clutch purse I had brought, pulled out a couple of blue pills, and said, “If you decide to let Mike fuck me, he needs to take this a couple of hours ahead. I think I can give him at least two orgasms.”
Mike’s eyes lit up. I could see he was starting to get hard. He said, “What do you think, Donna?” Donna begrudgingly agreed, but just this one time. Mike fucked me dozens of times. Anytime one of them got horny, they would call me. Mike got his doctor to prescribe Viagra, so I didn’t have to use my supply. As time went on, Donna increasingly enjoyed me fucking Mike.
As I was walking out, Mary Beth was just pulling in. I waited to talk to her. “Hey Andi, what are you doing here?”
“Visiting with your parents.”
I could see the wheels spinning. “Oh my god, Andi! Are you fucking my parents?”
“I’m not going to lie to you. I’m sorry. I’m a sucker for sex. Don’t be mad at me.”
“I’m not mad at you. I’m angry with my parents because they can’t keep it in their pants. Growing up, they had people over for group sex. I just don’t think they can help themselves.”
“Please don’t say anything to them.”
“I never do. Just be careful; they may get you into something you can’t get out of easily.”
Mary Beth confirmed what I had heard about Donna and Mike. I wasn’t sure what Mary Beth meant by “something I would have trouble extricating myself from.”
Over the next couple of weeks, I found myself at Donna and Mike’s house several times. I came up with a pattern that got all of us off. I would spank Donna’s labia and clit with a leather paddle until she said, “red.” While I was paddling Donna, Mike would hump me from behind. Once in a while, he could actually slip his rock-hard dick up my willing pussy. Both Donna and Mike would lie side by side. Donna would have a dildo in one hand and her powerful vibrator in the other.
I would mount Mike and use my technique to give myself several orgasms. Insert Mike’s cock, so it just barely is in me. I would come almost immediately. I would then slide him up to my G spot and pump out a couple of more orgasms. I usually feel him cum by now. I would then slam his cock all the way up me, hitting my cervix. This would almost cause me to instantly orgasm. I would continue with this very long, deep stroke until Mike came again. Donna became a real cuckqueen. She would get so turned on by me fucking Mike that she would have several very quick orgasms followed by a very long one.
Donna and Mike were so appreciative of all the great fucking and what I had done for their daughter, Mary Sue; they didn’t want to be paid for my share of the “rent” or food for the condo they had purchased for Mary Sue. So basically, except for a few fees, my second year of school cost me nothing except for some really great fucks.
Little did I see this friendship with Mary Sue’s parents would be so profitable, but more about that later.