Threesome Pleasures

In college my roommate and I fooled around many times. We were both bi curious and horny a lot. We met this guy and I wouldn’t say he was either of our boyfriend, he was a friend to us both and we were both attracted to him and him to us, so we asked if he might like to join us on occasion for bedroom playtime. Of course we didn’t need to ask him twice! He was game from the get go and the three of us had a lot of fun together many times. He lived in the building across the street from ours, so it wasn’t far to travel if one of us was feeling horny and wanted some company or cock.

He had a nice cock and I recall my roommate and I blowing him together countless times. He could stay hard even when he came and just keep going, so neither my roommate nor I ever went without, he could always satisfy the both of us. His cock in my pussy, stretched me out wonderfully. Many times he’d be fucking me from behind and my roommate was underneath me either licking my clit or I’d eat her out and he’d watch the show over my shoulder as he pounded my pussy.

He loved to lay on his back and have one of us ride him while the other sat on his face. He was well coordinated, and able to please the both of us at the same time, it was impressive, since a great many men have trouble pleasing one woman, let alone two at the same time. We were all young and in our early twenties with lots of energy and highly flexible and in good shape, so there was no shortage of fun had by all of us.

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Sharing the Night Together

I normally do not ever have one night stands, but I met this guy I really liked at a new club and I just didn’t feel like being alone that night. We went back to my place and I didn’t think I was going to have full on sex with him, but I knew we were going to play in some capacity and we did masturbate together and I gave him a hand job. He came on my tits and he loved watching me rub my pussy as I stroked his cock. I’m good with my hands and had one rubbing myself and the other stroking his cock.

He wanted to fuck of course, but I like to go by the old adage, “Always leave them wanting more.” So we didn’t fuck that first night, but we both certainly came and I know he’s going to call me again. He was very aroused as I stroked him over my lovely tits and I know he’s aiming to slide that dick into my pussy in the not too distant future. I want to see what that nice, thick cock will feel like spreading my pussy lips open.

I spread the precum all around his hard cock and got a good look at it close up as I was masturbating him, and although he didn’t touch my pussy as I masturbated myself, he certainly got a good look at her glistening, sexy self. I bet he just wanted to lay his tongue in between those lips and give them a big, wet French kiss. Maybe next time, loverboy! I will suck and enjoy his cock at some point, but if I gave in too quickly, why would he come back for more? Gotta tease the boys to a degree to keep them interested.

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Restaurant Fucking

My boyfriend had reserved a table at a restaurant in their private dining room. There was a public space for most of the restaurant, and the rentable private dining room with your own wait staff. It was quite expensive to get, but was popular for things like popping the question, anniversaries and things like that. I was surprised when we arrived when we were escorted to the private dining room, which I’d never been to before. It was lovely. The food was wonderful as always, and after the table was cleared the staff was nowhere to be seen.

Then he started to kiss me and touch me and I had the feeling I was about to be on top of the table. It was fun. He said no staff were going to be barging in on us and we had total privacy. I felt him lift me up to the table, and he feasted on my already wet pussy for dessert. He’s always been so good at licking me, it was divine, as always. I had to of course not make any sex noises, since we didn’t want to clue in the other patrons in the main dining room know what was going on in the next room.

He slid his cock into me and we fucked right there on the table. It was like a naughty, delicious secret having sex with likely a hundred people on the other side of the wall and just being in our own private room with no one being the wiser. I wondered if others had done this as well and if the staff really knew what people got up to behind the door. They likely did, but nothing was said. We got a slight smirk from the Maître d’ on the way out, but it might have just been his being a snob instead of actually knowing what we’d done. I’ll never know.

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Stretching Myself Out

When I was younger, I was afraid before I got my first boyfriend that sex was going to hurt a lot and I’d discussed it with a girlfriend and she told me what she’d done to prepare. She said she’d bought a few different sized dildos and trained herself on them well before she and her boyfriend actually did anything so she’d be not experiencing pain when they finally did do it. I figured it was worth a shot, so I ordered a set and did as she suggested over a few weeks. Callers will often ask about your first time and the sorts of things that happened then.

They do also like to hear about masturbation habits, so this sort of goes with both of those lines of questions. I told my boyfriend about this, since he was afraid of hurting me and he thought it was a good idea to do this as well. The big night came and my “training” had worked. I was not in any pain when we did it. I also had a set of nice dildos I used while masturbating. I was always afraid my mom would find them in my bedside table, but she never mentioned anything about them if she did see them. She was good about valuing my privacy.

I’ve loved sex toys since this, they gave me a very positive experience and have added a lot to my enjoyment of masturbation. There’s several that I have that I use depending on what I’m in the mood for. Many times my fingers alone are fine and I don’t need any toys to heighten my enjoyment, but sometimes toys are fun. Many guys call while using them as well, so everyone enjoys sex toys. They can just add some variety to your usual masturbation routine. Try a few and see which ones drive you over the edge.

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Jewish Desires

Sometimes you get a really unusual call that sticks out in your mind. I had one last night from an Orthodox Jew. You’d not think they’d be calling for phone sex, but it was very educational. Although married with three children, this man had only ever had missionary sex in total darkness with his wife, that’s it. No touching, no oral, and he didn’t even use his hands when he masturbated and said he never had, as it was forbidden. He was on his stomach dry humping and going to cum into one of his baby’s diapers to mop up the cum, it was very odd.

His life had been so sheltered, he said growing up they were not permitted a t.v., nor radio, let alone internet. Even a trip to the library was forbidden. Not until a week before his marriage at eighteen was he told anything about what happened between couples. How he ever found out about phone sex is beyond me. He fantasized about a different, normal sort of life, but would have been cut off from everyone he knew should he have left, so it was out of the question. His accent was heavy, so I asked where he was from. He said he was born and raised in New York City, but was so sheltered, he only spoke Yiddish until he was nearly twelve and then he was given limited English lessons, so he sounded like a complete foreigner even though he was not. It was pretty much home and religious school.

Sex was once a week at most, which is more than many traditional men I speak to get for sure, but most of them have had more than missionary in the dark with only one person. It’s interesting to hear such tales of isolation basically from what most would consider normal. There are many people out there among us leading very unusual, secret lives very foreign to us on every level.

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