Your response to Grandpa’s Guide to Girls was so flattering that it motivated me to write this sequel. You voted your approval and made very kind comments about the story of Grandpa Frank helping young Ben woo his first girlfriend.
You need to know why I placed this sequel in the “first-time” category. Ben is not a virgin when he arrives at college, but every sex scene in this 10-part sequel has at least one character having at least one “first-time” experience. Oral. Bondage. Anal. Roleplay. Reluctance. Facials. Threesomes. New partners. The recurring theme is the gradual surrender of diverse kinds of innocence.
As you know, many stories on Literotica defy categorization. It’s almost impossible to give readers all the information they deserve while deciding what stories to read. If you’re looking for a tale of young lovers having erotic experiences for the first time, you’ll find it in Grandpa’s Guide to Women. Just know that these characters surrendered their virginity before this story begins.
Part 9 describes the big night when Ben, Julie and Sonya finally have their threesome.
All characters are adults over 18.
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My roommates were surprised when Sonya came over. They were used to seeing Julie visit. They were vaguely aware of the fact that I dated Sonya, too, but with her, I always spent the night at her sorority. This was the first time Sonya set foot in my dorm.
We met at my place because I have the biggest bed. If we planned to have a threesome, we needed the biggest mattress we could find. Julie and Sonya both sleep in single beds, while I have a full-size. It’s smaller than a double, but large enough to be comfortable with two people. We’d soon find out if it was big enough for three.
“Are you as nervous as me?” I asked.
“Of course I am,” Sonya said. “I’ve been thinking about this all day. I can’t think of anything else. How’s Julie?”
“Scared,” I said. “This is forcing Julie way out of her comfort zone. Fortunately, she enjoys doing as she’s told.”
“Good to know,” Sonya said.
“I think this will work best if you fit yourself into the roleplaying dynamic Julie and I use these days,” I said. “She calls me ‘Sir’ and I call her ‘Young lady.’ I’ll ask her to call you ‘Ma’am’ if that’s alright.
“That’s more than alright,” Sonya said. “I just got a little bit wet.”
“I’m pretty sure I understand what Julie likes when I tell her what to do. It would probably be best if you follow my lead. We’ve gotten to the point where we do some pretty kinky things, but we got here one step at a time.”
“I’ll do my best to be firm, but not overly demanding,” Sonya said. “I don’t want to frighten her.”
We talked for a little, then Julie arrived. My roommates thought it was extremely weird that both of my girlfriends were in the same room at the same time. They gave me an odd look as I closed and locked the door.
“We’re very glad to see you, young lady,” I said. “You look beautiful.”
“Thank you, sir,” Julie said. She was trembling and her voice was shaking. I suspected it took every bit of courage she had to do this.
“You’ve met Sonya, haven’t you?”
“Yes sir. Hello Sonya.”
“Hello, young lady,” Sonya said with an authoritative tone. “I’m glad to see you. You look lovely. Hot.”
“Th-th-a-ank you,” Julie said.
“It would be best if you called Sonya ‘Ma’am.’ You can do that, can’t you?” I said.
“Yes sir. Yes ma’am.”
I gave Julie a kiss and ran my hand down her back. It made her shiver. I gave her another gentle kiss, which made her shiver even more.
Sonya walked toward us. Without saying a word, she leaned forward and gave Julie a very delicate kiss. Sonya reached behind Julie, and we both ran our hands up and down her back and sides. Julie looked so frightened I felt sorry for her. I hoped I wasn’t pushing her farther than she could go.
Wrapping my other arm around Sonya, I drew all three of us into a hug. Julie closed her eyes and seemed to be hyperventilating.
“Relax. Try to relax,” I said.
“I’ll try, sir,” she said.
Sonya caressed Julie’s cheek. “It’s beautiful that you are so obedient,” she whispered. “It’s very sexy. I think you’re the sexiest girl I’ve ever met.”
“Thank you, ma’am.”
“Can you obey me the way you obey your Sir?”
“I’ll do my best, ma’am.”
Things seemed to be going well, so I pulled Julie toward me and gave her a passionate kiss that left her breathless. I nodded to Sonya, who leaned in and gave Julie a kiss that was even more soulful. Julie had been trembling; now she was shaking. But I could tell she was aroused. She had the look she always gets when she likes what I’m doing.
Sonya and I took turns kissing Julie for a while, then I kissed Sonya as Julie watched. I knew Julie was ready for more, so I took her hand, placed it on Sonya’s breast, and squeezed.
“That feels wonderful, young lady,” Sonya said breathlessly. “Do that again.” Julie squeezed Sonya’s breast by herself.
Everything felt wonderfully erotic. We weren’t doing anything overly sexy, but we all knew where things were going. The anticipation was delicious. I pressed Julie and Sonya together so their breasts rubbed.
“You feel so soft,” Sonya whispered. “I want to touch you all over.”
It was time to get Julie out of her clothes. I’d already told Sonya that I like to stay dressed until Julie is completely naked, so we removed Julie’s outfit together. We took our time. Julie looked like she was about to panic, but she managed to hold still.
Sonya and I both made a show of looking at every part of Julie’s naked body slowly and carefully. Julie loves putting herself on display for me, and I felt sure she’d like it even more when Sonya’s gaze joined with mine.
“Get on the bed, young lady. Get on your back,” I said.
Julie kept trembling as she got in the middle of the bed. Sonya began caressing Julie’s breasts, causing her nipples to get as hard as I’d ever seen. I took off my clothes and got on one side of Julie while Sonya stripped off and got on the other. Julie seemed to be overwhelmed with sensation as both Sonya and I explored every part of her body.
We’d already agreed that since this was our first threesome, it would be all about Julie. We’d put her needs first, doing whatever seemed to please her most. If we had more threesomes in the future, we could take turns being the center of attention.
Sonya began licking and sucking one of Julie’s breasts, and I did the same to the other. “Yes… ohhhhhh… yes…” Julie said as we simultaneously sucked her nipples between our lips. That seemed like the most positive sign from her since we began. Maybe it meant that Julie was less frightened and more aroused. It must have felt good having two people stimulate her big, beautiful boobs at the same time.
I moved up so I could kiss Julie’s lips, and I saw her looking at me through half-closed eyes. “Oh, sir. Ma’am,” she said softly. “This feels good.”
It was thrilling to see how well things were going. I was so aroused I could barely control myself. My cock throbbed and ached. Sonya rose up and held her breasts over Julie’s face.
“Suck me, young lady,” Sonya said. “Suck my boobs.”
Julie responded slowly, but soon she was feasting like a starving woman, taking Julie’s breasts in her hands as she sucked and licked her nipples.
Rising up on one elbow, I reached down and spread Julie’s legs. By this time Sonya seemed to be getting impatient. Julie had gotten all the attention so far, and I think Sonya was ready for some stimulation. She got face-to-face with Julie and began rubbing their breasts together. She straddled Julie’s leg and slowly humped it.
As Sonya played with Julie’s breasts, I reached down to massage Julie’s warm, wet pussy. She began moaning softly as I ran one finger up and down between her lips. Julie jerked when I put a finger inside and began sliding in and out like a little cock. I felt a hand reach out and grip my erection, and it took a few seconds before I realized it was Julie, who seemed to be letting me know she was ready for more.
Sonya could tell what Julie wanted, so she turned about on the bed and twisted Julie’s body around until she had her in a scissors position. Sonya started grinding their pussys together, and it was pretty clear that Julie loved it. There was no way to tell that a few minutes earlier Julie had been afraid. There was no trace of fear shown in the way she moved her hips up, down, and around in response to Sonya.
It was fun to watch, but I wanted to do more myself. I stood next to the headboard and took Julie’s head in my hands.
“Open your mouth, young lady,” I said softly. Julie gave me another wide-eyed look. She knew what I wanted. She opened her mouth, and I put my cock inside. I wasn’t rough or anything, but I wanted Julie to know how it felt for me to fuck her face at the same time Sonya worked on her pussy.
I held her head gently but firmly, pulling her to me forcefully enough to shove my cock all the way to the back of her mouth. I didn’t force her to deepthroat me. That’s not what I wanted right then. I wanted Julie to feel like she was having sex with two forceful, dominant people who were both committed to doing things that would give her no choice but to enjoy it.
I guess Sonya wanted to do more for Julie because she pulled away. Soon she was between Julie’s legs, getting ready to go down on her.
“Are you ready for me to eat your pussy, young lady?” Sonya asked.
I pulled my cock from Julie’s mouth so she should answer. “Y-e-e-s-s ma’am,” she said. I’d eaten Julie’s pussy dozens of times, but she’d never felt a woman’s tongue between her legs. It made her nervous, which was adorable. I knew she’d love it. What’s not to love? It was inevitable that she would like to get that from Sonya. The only thing challenging her was the idea of being so intimate with a woman instead of a man.
Sonya was enjoying herself. There was no sign that this was her first time going down on a woman. Julie cried out in shock when Sonya began licking, sucking, and nibbling her warm wetness. It was beautiful seeing Julie squirming around on the bed as Sonya ate her pussy.
I pulled my cock from Julie’s lips one last time and walked to the end of the bed, where Sonya was bent over. I hadn’t touched Sonya’s pussy yet. It was glistening, and it made me want to plunge my cock inside her. I’m sure you won’t be surprised to read that I didn’t do that.
You must know by now that I do everything in my power to slow down and make sex last. Instead of slamming into Sonya, I took my cock in one hand and rubbed the head up and down the length of her crease. Her mouth was clamped on Julie’s pussy, but she still managed to make sexy little sounds that let me know she enjoyed what I was doing.
Using the tips of my fingers to pull her lips apart, I guided my cock to the opening of Sonya’s passage. I teased her for a long time before I finally gave her what she wanted.
“Uuuuuummmmmmm,” she said when she felt my shaft push inside her. I felt good. I’d set this up, and like any good host, I wanted to make sure my guests were having a good time. Julie was obviously very aroused by having a woman eating her pussy. Sonya obviously enjoyed being fucked from behind by a cock while she was going down on a pussy.
The whole thing was so stimulating that I knew I had to be careful. Before this threesome even began, I realized that it would be especially challenging for me. I had to satisfy two women, not one, and they both deserved to get as much cock as they wanted. By this time I had a lot of experience delaying my orgasm, but I’d never had to delay it this much. I needed to concentrate if I expected to use my cock to give both women nice, strong orgasms. I was glad I’d remembered to masturbate earlier; that always helped me last.
After a few more minutes of this, Julie climaxed. I love how easy it is to make that girl cum. She is the most responsive woman I’ve ever known. Julie seemed to like all kinds of sex, especially role-playing where she acted like a sub. It made sense that a girl who was so naturally submissive got a special thrill from being dominated by two people at once. I’d worried that she’d have trouble responding to Sonya because she had misgivings about sharing me with her, but that didn’t seem to be interfering with her enjoyment of her very first threesome.
After Julie climaxed Sonya pulled away from Julie’s pussy and laid her head on her inner thigh so she could focus on the motion of my cock. “Ohhhh… Ben…” she said as she began to cum. I don’t know if she was more excited by the experience of eating Julie’s pussy or riding my cock, but I doubt that it makes any difference. She seemed to enjoy both of those things, and I felt confident she’d enjoy whatever happened next.
I pulled my cock from Sonya’s throbbing pussy and tried to relax. It was time to let my cock calm down. I noticed that Sonya’s face was all wet because it was covered with Julie’s pussy juice.
I moved up and began kissing her. It felt wild to taste Julie’s pussy on Sonya’s lips, and I wanted to get as much of that taste as possible. I’d never tasted anything like that before. I began licking Sonya’s face, cleaning up every drop on her cheeks, lips, and chin.
“You can be a real pig sometimes, you know that?” Sonya said, giggling. I knew it was a joke, but it was also true. Licking Julie’s juices from Sonya’s face gave me a gluttonous thrill. I hope I have many chances to do that again in the future.
I laid down on one side of Julie, and Sonya laid down on the other. We all hugged as both women recovered from their orgasms. My boner pressed into Julie’s thigh, and I hoped she wouldn’t touch it. If my cock could rest for just a few more minutes, I would be able to give at least one of the women enough attention for a final climax.
I rolled Julie over on her side so we could spoon. My cock fit perfectly in the crack of her ass. Sonya pressed her boobs into Julie’s boobs and lavished deep, soulful kisses on her lips. I could reach Sonya’s back, so I pulled her toward me until the three of us were pressed into a tight sandwich, with Julie in the middle. Sonya looked at me and smiled. It was reassuring that she was having such a nice time.
Sonya moved lower, kissing Julie’s neck, then going down even farther to caress her breasts. I heard Julie breathing deeply as Sonya treated her to increasingly intimate attention. Julie wrapped her arms around Sonya and drew her even closer.
I thought my cock was ready for more, so I moved it into position to enter Julie’s pussy from behind. I felt Julie change the angle of her bottom to make it easier for me, and I slipped my cock inside her. She let out a happy little sigh. Julie had already enjoyed one orgasm, and I was ready to give her another.
Since I had to be careful to avoid cumming too quickly, I moved in and out very carefully, going slightly deeper each time. I closed my eyes and concentrated on what I was doing. After a few moments, I felt Sonya’s hand brushing my cock. She was touching Julie’s pussy from the front, caressing her clit, and from that angle, her fingers reached my cock as I moved in and out from the back.
Julie started squirming around in ways that let us know she loved what we were doing. Of course, she enjoyed feeling Sonya lavishing attention on her breasts and clit at the same time I was pressing deeper and deeper into her pussy. It was the kind of thing Julie could not resist.
I knew it would take a lot of work to make Julie excited again, so I settled in for a long, patient push. It went on, and on, and Julie’s arousal grew with glacial slowness. My hamstrings began to ache, but that didn’t matter. I had to continue for as long as it took to make Julie cum again, even if it took every bit of endurance I had.
Julie began whimpering and letting out soft little yelps as we played with her. She moved her hips back and forth as Sonya and I kept stroking. Her motions got more energetic. More frantic. My leg muscles really began to hurt, but I kept thrusting anyway. This was our first threesome. I was going to do whatever I could to make it pleasurable.
I’m not sure how much longer this continued. I just know that I was soon covered with sweat, and my hamstrings felt like they were on fire. It was a welcome relief when Julie finally climaxed. It meant I could relax and let myself cum. I don’t think I’d ever tried to delay my orgasm that much before. Julie felt my cock throb as I came, and came, and came some more. I was overflowing with cum by then, and I’m sure Julie could tell.
Sonya felt it, too. She stopped stroking Julie’s clit and reached for my cock just in time to feel it as I climaxed. It was a powerful blend of agony and ecstasy, with my aching muscles and my overtaxed cock finally able to do what I’d wanted for so long.
I was tired. It had been an erotic marathon. I closed my eyes and fell asleep immediately. I think Sonya and Julie slept also, but they woke up again soon. I felt one of them gripping my hard cock. I don’t know if the hand I felt belonged to Julie or Sonya. All I can tell you is that we began having sex again. It felt wonderfully natural and relaxed.
We slept again, woke again, and had sex again. I’m glad we didn’t have any early classes the next morning because we needed to sleep late. We enjoyed a final session of lovemaking, then reluctantly got out of bed and put our clothes back on. My roommates were sitting in the common area when we finally exited my room. I don’t know what they expected.
They’d seen Julie and Sonya come to my room the previous evening, and they must have heard a lot of the moaning and groaning all night. They’d tried not to be too obviously envious during the nights I spent with one woman or another, but expecting them to ignore a threesome was unreasonable. I didn’t know how to react, but Sonya did.
“Yeah. We confess, guys. This is just what it looks like,” she said. “Your roommate Ben has been up all night fucking us so hard that we’re going to be walking with a limp all day. If you know any women who need to take a nice long ride on a good, hard dick, you should refer them to Ben. He’s very good at that kind of thing. Anyway, we’re going to breakfast. After burning so many calories all night, we need to put some food in our bellies. We need to hydrate. See you later, boys. I’m sure we’ll be back very soon.”
I managed to avoid laughing out loud until we were out of the room and halfway down the hall.
“Subtle,” I said.
“I hope it wasn’t too subtle,” Sonya said. “I wanted to clear up any confusion over the presence of two women in your room all night.”
“I don’t think any of them are confused,” I said. “And I have a feeling we haven’t heard the end of this.”
That turned out to be true. I got a lot of strange looks over the next few days. Once again, we were the subject of gossip in one dorm, two sororities, and with a long list of miscellaneous busybodies. The regular flirting I experienced got a little more intense.
I wondered if anyone would have the nerve to ask me about it. After thinking for a few hours, I decided what to do. I went online and downloaded a photo that ought to silence any questioners.
The guy who finally asked was my roommate, Mike.
“Alright Ben, you need to explain yourself,” Mike said. “How in the hell are you doing so well with women? I can barely get anyone to date me. I haven’t found anyone willing to spend the night. You’ve been spending the night with one woman or another for months, and now you spent the night with two. What the actual fuck, Ben?! What’s the story?”
I was glad I’d prepared an answer. I got out my telephone and swiped to the photo I’d downloaded. It was a dick pic of some porn actor who had a cock the size of my forearm. I don’t know if he was freakishly huge or if somebody used PhotoShop to make him look that way.
“A girl I know took this picture of me,” I said. “She showed it around, and now I’ve got more women chasing me than I can handle.”
I’d hoped to deliver that line well enough for Mike to believe me – at least for a bit. But he wasn’t fooled for a nanosecond. “Right. That’s you. Uh-huh. I’m sure it’s a burden carrying around a piece of meat like that.
“I can’t imagine how hard it must be finding underwear that fits.”
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It’s been a good semester for our intrepid crew. This story concludes in Part 10, when the Christmas break allows them all to go home, where Ben has a reunion with his high school girlfriend Beth.