The Long Goodbye
Chapter 33 - The Fun Stuff (Part Three): Partying With the SAAD-ists and the Amazing Anal Ann!
I don't know how else to put it. Stephanie and Abby had their way with me overnight after Ann and Delaney left. I was their overnight "fuck toy" as long as they could keep me hard (and they did find ways to keep me hard). I wasn't complaining.
They rode me, first one, then the other. Back and forth it went. After multiple turns of this alternating fucking, Abby climbed off me and dropped her pussy to my mouth. I felt Stephanie slide down my cock while Abby was sitting on my face. They changed places after a bit with my cock inside Abby and Stephanie sitting on my face. They did this several times before I felt myself getting ready to cum. I was inside Stephanie but I couldn't say anything because Abby had her pussy pressed down on my mouth and joying her ride as my tongue was exploring her pussy. I thought about trying to lift her off of my face to let them know that I was about to cum, but figured "What the Hell!" They'd figure out I was cumming. My body tensed up and moments later my cum was shooting inside Stephanie while I was trying to keep from being smothered by Abby.
I finished cumming and before I started to get soft, Stephanie lifted herself off me (at Abby's direction) and Abby lifted off my face and took Stephanie's place. Abby got my cum covered cock into position and slid me in her even though my cock was very sensitized. Once inside her, she carefully rocked on me to allow my refractory period to pass without going completely soft. Stephanie took her cum-filled pussy and positioned it over my mouth and settled down to allow me to lick and suck my cum out of her. It only took a few minutes before I was ready to start stroking again and I indicated that by moving my hips to change my penetration depth in Abby. Soon, we were at it again.
During one of the switches Abby told me to let her know when I was getting close so that I could cum inside her, too. Abby was on my face as I felt myself getting close and I tapped her legs near her hips. She didn't get the message at first (apparently being so absorbed by the feeling of my tongue) so I tapped harder. She realized that I was signaling that they needed to switch so that I could cum inside of her. Stephanie got off my cock and moved to the side as Abby slid back on me. It took about two minutes of our combined stroking before I told her I was about to cum. She sat up straight and settled down on me so that I was in her as deep as I could be. Right after I started to cum and she felt those first couple of spasms, she came, too.
As our orgasms subsided, Stephanie leaned down and over to give me a kiss.
"Your face smells funny!" she said and then moved out of the way so that Abby could lay down on me. She wasn't in any hurry to pull me out of her and it was about five minutes before I softened so much that I slipped out of her. She moved to the side, turned around and sat down on my face (once again) so that I could taste our combined juices and clean her out. Finally, she got off my face and the two young women positioned themselves beside me.
"That was amazing," Stephanie said. At some point Stephanie asked Abby if they could bring me with them to Corvallis (so that I could be their ***Sex Slave*** and tend to their every "need"). That had an appealing and exciting sound in the moment. I knew that wasn't going to or couldn't happen. But, I was amused at the possibility of being their sex slave (or maybe they would become mine?). There was a bit more fucking as I turned over, had them spread their legs and I went back and forth between them. I didn't cum. I just wanted us to have a few strokes before we all went to sleep.
We all fell asleep in a giant wet spot on the bed with them on each side on me. The tape finally ran out and shut down the video recorder.
I woke up fairly early and looked outside the window after heading to the bathroom. It was light and after sunrise, but a veil of clouds and mist hid the sun. Days like this could clear if it was a marine layer that could eventually burn off around noon. At that moment, though, heading back to Rooster Rock seemed doubtful due to the weather.
I crawled back into bed between them. This stirred both of them awake. "Good morning, ladies" I said to them.
"Uhhh, what time is it?" Abby asked.
"A little after 7," I said. I pulled the covers back over us and they snuggled up next to me. I drifted back to sleep until just before 9 AM. This time it was Stephanie and then Abby getting out of the bed and heading to the bathroom. I heard Stephanie say something about her hair being a well-fucked mess as she walked past the mirror over the sink. When they were both back in bed, I asked if I could get something for them. I was thinking more about the continental breakfast that was available.
"Yes," Stephanie said. "I'll have your big sausage special" as she reached down and grabbed my cock.
"I'll take some of that, too," Abby said and her hand joined Stephanie's stroking my cock. "With that special cream sauce of yours," she added.
"You've got to save some for later," I said. We snuggled and cuddled together for a while before I finally got up and went to the breakfast area to bring us something to eat in the room.
There was still a dense cloud layer and it was much cooler on this day compared to the day before (Friday). It still didn't look like this cloud layer was going to burn off.
Stephanie, Abby, and I all got in the shower together to wash off the previous night's sweat and other bodily fluids from all the fucking we engaged in (plus the funny scents on my face).
The "girls" got dressed and decided that they would go to each house to pick up a few things and to let their household know that they were still hanging out together. Later, I found out that Stephanie's parents thought that she was staying with Abby and Abby's dad thought that she was staying with Stephanie. From a certain point of view, that was true. But neither one of them told the parents that they were staying with me and fucking with me.
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By 11 AM, it seemed pretty evident that this was not going to be a great (nude) beach day. Abby and Stephanie agreed to contact Ann and Delaney to let them know that we were postponing the trip up the Gorge and that we'd meet back at my hotel room around 3:00 PM. While Stephanie and Abby were gone, I went to a nearby Fred Meyer store to pick up a few items. Housekeeping changed the sheets and towels while we were all out of the room.
I got back to the room and didn't expect any of the women back until approximately 3:00. I stripped down to some shorts and dozed off while I waited for their return. I awoke to a knock on the door and Ann arrived first (very early just before 2:00 PM). I thought that maybe she got confused about the time but we had a nice conversation while we were waiting. She told me she was nervous about what she was about to do (surrendering her anal virginity). I told her that I understood and we talked about what it was like with Abby (and with Catie) as they had been anal virgins when we met.
"But they were ready to try it," I told her. "No matter how much pressure you sense from your girlfriends, you don't have to do this and you certainly don't have to do this with me," I assured her. She wanted to know more about what we were going to do and I answered all of her questions.
"Is it going to hurt?" seemed to be the biggest concern of hers.
"Yes," I said. "It will not be painless. I will do what I can to minimize the pain as much as possible. I will have us lubricated as much as I can and go slowly and only as fast as you want. Like I told you yesterday, if you want me to to stop, I'll stop. If you want me to pause, I'll pause." I told her that's what I did with Catie and Abby, that I took it nice and slow and would stop to allow any pain associated with being stretched to subside and to allow them to become accustomed to my cock in their rectum.
"I don't know, you're pretty big," she said.
"Have you talked with Abby about this?" I asked. She had. "And what did she tell you?" I asked. Ann summarized what Abby had told her ending with "you're pretty big." But she also told me what I already knew; it turned out that Abby loved anal sex as part of what she and I explored together.
Our conversation turned away from anal sex to the previous night. She told me she really liked the experience and it was very different from her experiences with the guys she had dated and had sex with (that were her age). I inquired in what way.
She had watched the videos that Abby made (multiple times) and whether they were times where it was just Abby and I, or times where it was Catie, Abby and I, they made her very horny. And although she and Abby had talked about what it was like, she could only imagine (and did imagine) what it would be like.
"Was it what you expected?" I asked.
"It was so much more. You seemed so much more focused on us...on me," she said. She thought she might be more self-conscious and inhibited about being in this type of situation with her girlfriends because she wasn't as well-endowed with larger breasts or wider hips like her friends did. But, it started to feel so good that she forgot all about it.
"Oh, and that thing you do after cumming in me...in us...It felt incredible," she told me. "I couldn't believe how good it felt with Abby and I. And then, after you came in me, to have your tongue swirling inside me while you and Dee (Delaney) were fucking...." Her voice trailed off. I leaned over and gave her a hug and kisses.
She confided that she was "so wet" from talking and thinking about it and that she wanted my cock back inside her.
"Do you think that will be okay?" she asked.
"Is that what YOU want?" I asked. She told me that she did.
"Then, it will be okay," I said. I reminded her that we might get interrupted by a knock on the door or, if was Abby, she had a key to my room. But this was for her. She stripped out her clothes and then pulled my shorts off me. When she got back on the bed, she wanted me on my back so she could be on top.
She was right. She was very wet and, as she reached between her legs to position my cock to enter her, I sat up and sucked her nipples. The combination of sliding down my cock and my sucking her nipples was all it took to have her cumming. Our conversation had been our foreplay. After her first big orgasm, she continued to ride me. After a while, I had her get off me and I entered her from behind. She had a very cute ass and from this position behind her I started describing what I saw as my cock slid in and out of her. Then I started to describe what I would see if I slipped my cock into her ass. I thought she might ask me to enter her anally then. But, she did not.
I eventually turned her over on her back so that we were face to face with me on top. From this position, I could stroke her while I was upright on my knees with her legs spread wide or held by me over my arms or my shoulders. When I laid back down on her I asked her if she was ready for me to cum in her again. She said she was and she wrapped her legs around my hips as I continued to vary my strokes inside her.
I felt the sensations building towards orgasm go from a slow buildup, to a quickening buildup, to the flood of what was about to cum. I looked into her eyes and said "Here I cum!"
We kept our gaze focused on each other. As I've mentioned before, it's easy to zone out, look away, and be in my own little orgasm world. But I was both relaxed and concentrating on looking at her while I was cumming, to study her eyes and her face. Suddenly, I saw her eyes roll back as she tilted her head back, took in a little extra air through her mouth and then exhaled as she experienced the beginning her own orgasm. I loved that; not cumming at exactly the same time but one orgasm triggering the orgasm of your partner.
After our orgasms subsided, we were laying there face to face. She was smiling and told me how good it felt. I, of course, was still inside her and trying to stay in her as long as I could. She squeezed her vaginal muscles a couple of times and we both giggled at that (but I wasn't soft enough yet for her to squeeze me out). I asked if she was doing okay and she said she was and that she was glad that we got to spend this time alone together.
"When you were back there behind me, describing what you would do to me" she said, "I almost asked you to take your cock and put it in my ass."
"Why didn't you?" I asked.
"I don't know. I wish I had; I was so ready to have you take my ass," she said. I told her that if she was ready for me then, then she'd probably be ready for me later. All this talk about anal sex slowed my softening but I eventually felt myself starting to slide out of her. Before I had a chance to ask or even move, she asked that I stay there with her like we were and to feel my cum running down between her butt cheeks as it leaked out of her.
We didn't say much as we laid there. Her arms were wrapped over my shoulders, her legs were wrapped and crossed over my hips. I was surprised we hadn't been interrupted yet and it gave us time to savor our connection. She placed one of her hands behind my head and was stroking my hair.
"This is the best part about making love," she said to me. "I don't know why you guys want to jump and get away from us."
It was a very broad and general statement and I knew what she was talking about.
"Some of us don't," I said.
"You're the exception," she said. After a few more minutes of just laying there with each other, she told me that she needed to get up to pee. We disentangled and I rolled out of the way so that she could get off the bed. I watched as she disappeared around the corner to the bathroom. A minute later I heard the toilet flush and Ann returned to the bed.
"You're a cum fire truck," she said. "There's so much dripping out of me."
"Are you sure you don't want me to clean you?" I asked. She was willing but then she'd want to keep going for another round and she thought she'd wait until her friends were back.
It was now just after 3:00 PM and nobody except Ann was in my room. "I wonder where everyone is?" I said/asked.
"I do, too," Ann responded. "Abby called me and told me to be here by 2:00 PM." That was odd. I thought we had agreed to 3:00 PM. Ann crawled back in bed with me and we cuddled next to each other as she told me about getting ready to go to nursing school. I knew that Abby had considered nursing as a career path. After her mom's and sister's death, she just didn't think she could do that.
I heard a key in the hotel room door at about 3:10 and the door opened. It was Abby and she walked into the room, saw us in bed together and smiled a knowing smile.
"Did you guys get started already?" she asked.
"Yes," said Ann. "We've already finished and were waiting for you!"
Ann said "I thought you were going to be here."
"I was," Abby said. "But then I thought you two needed some time together. That's why I told you that it was okay to get started without me," Abby told Ann. "Did you have a good time?" she asked. Ann replied that we did. Abby closed the door to the refrigerator and walked towards the bed. Abby was wearing a halter top and a cute pair of knit shorts that were just short enough to reveal the buttocks folds at the top of her hamstring muscles.
As she walked to the bed, she took off her top, slipped out of her shorts and panties and got on the bed next to Ann. Abby patted the bed and told me to "come on. We don't bite..." She laughed and then said, "We do, but very gently."
"That's good," I replied as I moved beside them. Ann went on to describe our sexual interlude to Abby. When she got to the point where she was describing us in the doggie position, Abby asked if we tried anal sex, then.
"No, he was telling me what he saw and what he would be doing if he was entering me anally. And I remember watching the tapes and what you told me. I wanted to so bad and now I wish I had because I wanted to feel him inside me. But I chickened out."
Ann turned to me and said "I'm sorry." I told her not to be. It was her choice when she was ready. "Remember, I'm not one of those high school boys who can't see beyond the end of his cock." Ann was still worried about the pain.
"It's like when you lost your virginity." Abby looked at me. "Excuse me, surrendered your virginity. I surrendered my vaginal and anal virginity to him so I know what he feels like that first time. I'll be here to help you through if you want any help. But he's really good at it." Abby patted me on my thigh and told me (so that Ann would see and hear) "I do like it when you're in my ass."
"I know," I said.
Ann laid back against the pillows, legs spread towards me. She was sitting on the hand towel she had brought from bathroom. Abby looked down at Ann's spread legs beside her and saw the leakage from Ann's pussy.
"Are you wet? Or are you leaking cum?" Abby asked. With a deep sigh Ann said "both."
"Me, too!" Abby said. She leaned over and said, almost in a whisper, "Soon you'll have his cum someplace new...in your ass!"
Ann had her eyes closed and let her fingers begin to trace over and around her pussy.
There was a knock on the door. I looked through the peephole and it was Stephanie and Delany.
"Ladies!" I said as I opened the door. "We've been waiting for you."
They stepped into the room and saw Abby and Ann naked on the bed. Ann had stopped rubbing herself but she was still reclined against the pillows. Stephanie got undressed and busied herself with setting up the video camera on the tripod. Delaney stripped and put her clothes on one of the chairs in the room before joining Ann and Abby on the bed. I went to the far side of the bed (away from the camera or the left side looking from the foot of the bed) and stretched out there while Stephanie finished setting up and put in a new tape.
"And action," Stephanie said. She got of the bed with the rest of us.
We reviewed the ground rules again and what the plan for the day was. Although anal play was the plan for the day, Ann had already had a vaginal filling. Abby, Stephanie, and I answered any questions that came up. Ann and Delaney had never experienced (or didn't remember) enemas. Although I would be giving them, Stephanie and Abby were willing to assist with Ann and Delaney. Abby "passed" on the first enema (and subsequent anal sex) of the day to allow Ann to go first. Stephanie got up and detached the video camera (it had a long enough cord to see around the wall that divided the bathroom area from the rest of the room) when I asked Ann to come with me to watch the enema preparation process.
Ann got up and the two of us walked to where I had one of the enema bags stored. I turned on the water in the sink to get the warm water to the faucet. Once it came up to temperature I adjusted it to maintain a constant temperature to fill the bag. I invited Ann to feel the water temperature to let her know that it was warm (but very pleasantly warm). I explained to her that we were only going to do about a quart of warm water.
"How much do you and Abby do?" Ann asked.
"It depends," I said and explained the reason for smaller enemas for basic cleansing of the rectum and lower colon.
"If we want a more thorough cleansing we'd go with a larger volume. But it takes more time and effort to have a more thorough cleanout and that's why I'm using a smaller volume," I explained.
"We can do a larger volume later if you're interested in feeling that," I offered.
After the bag was filled to the desired level, I had Ann put out her hand to carry the bag by the hook and gave her the nozzle to carry in her other hand and directed her back to the bed. She walked towards Stephanie (the video camera was on her shoulder and from my perspective, she, as a naked videographer, was quite a sight). Ann walked past Stephanie and back to the bed area. She turned to me and asked "Now, what?"
I asked my other assistant, Abby, to take the bag and the nozzle from Ann, I placed a folded towel on the bed and had Ann get on her knees on the bed above the towel.
"Spread your legs, put your head down on a pillow if you want, and get comfortable. While she was getting into position, I took a small jar of petroleum jelly and put it beside her on the bed. Stephanie had brought the camera back around to get a good view of what would be happening next.
I placed my hand on her left hip and asked if she was comfortable. She said she was nervous, but comfortable. I popped the top off the jar with my right hand and then dipped two of my fingers into the gooey jelly. I moved forward slightly so Ann could look over at me while I was explaining what I would be doing next.
"Normally, with an experienced partner, I would use a different lubricant and we'll be using that later. But this doesn't wash away so easily with water and will help you with any friction. Do you understand?"
She said she did.
"I'm going to insert my finger into your bottom to spread the jelly around. I may insert the second one depending upon how tight you are. Do you understand? " She did.
"Okay you're going to feel my finger tracing around your anus first. Are you ready?" She nodded her head. I stepped back behind her and got on the bed. I used my left hand, which had been on her left hip this enter time, to rub her buttocks as I prepared to lube her. I know that for someone who had not done this before, this was an extremely vulnerable sensation. Particularly when you know someone's finger is about to slide into your ass.
I angled my left hand to spread her cheeks a little wider and my right index finger made contact with the outer muscle ring. She jumped at the initial contact and then seemed to relax as I began to spread the petroleum jelly around the outside of her anal opening.
"Are you feeling okay?" I asked her. She answered with a rather dreamy "Umm-hmm." I continued to circle around and over the center of her anus with the flat part of my index finger while applying gentle pressure. I changed the angle so the tip was more pointed into position to enter her. I continued to move in circles with gentle but persistent pressure. The tip of my finger began to penetrate the center of the muscle ring and I told her that she should start feeling my finger slipping in as I rubbed an different set of nerves. She didn't flinch.
"The tip of my finger is in you," I said as I continued to rub the area where my finger was inserted. "Are you ready for more?" She said she was and continuing the circular motion my finger slipped into her rectum. I traced along the lower rectum walls and the inner muscle ring of her anal sphincter muscles.
"That feels good," Ann said.
"My finger is all the way in." I said as I during a slow swirl inside her rectum. The other young women were mesmerized by this and not a word was said.
"Are you ready to try a second finger?" I asked. She said she was. I pulled my index finger out just far enough to place my middle finger beside it and began the process again. She told me that it really felt good as I continued to rub the outer surface. I changed the angle and told her when I was beginning to enter her with two fingers. Again, no rush to get in but my fingers slipped in relatively easily. I turned my head back and asked Abby to purge the enema hose of air, which she did. After a minute or two of running my fingers around her rectal walls, I told her that I was going to remove my fingers and prepare to insert the enema nozzle.
I slowly withdrew my fingers and I had Abby run the nozzle across my fingers to lubricate the nozzle with any residual petroleum jelly that remained between my fingers. I took the nozzle from Abby and placed the tip against her anus. I still had my left hand at the base of her spine to spread open her cheeks.
"Ann, I'm going to insert the nozzle. It's much smaller in diameter, but will go in deeper. Are you ready?" She said she was and with a gentle push, it slipped right into her. I grabbed the base of the nozzle with my left thumb and forefinger to hold it in place. I could release the clamp with my left fingers. I stood up and took the bag from Abby.
"How are you doing? I asked.
"Fine," Ann said.
"I can control the rate of flow into you by how high I raise the bed or by how far I open the clamp. If the enema is flowing into you too fast, let me know. You're going to feel a little cool water from the hose before you feel the warm water from the bag. Are you ready?" I asked.
"Yes," Ann said. I clicked the clamp open with my left hand and the enema began to flow into Ann's rectum.
"Oh, that feels so strange."
"Are you okay?" I asked.
"Yes, keep going. It feels good. Nice and warm."