Sean's Surprise

Another true story from my convoluted life.

I am Sean. I am a white man with very limited sexual experience.

I graduated college as a sexual virgin and married a sexual virgin who insisted on our always using a condom when we had sex (she wanted to see how much cum I produced each time), unless we were making a baby.

I blew that relationship with a one night stand who was on the pill. I felt so guilty about cheating that I told my wife immediately and she took the kids and moved back in with her parents.

I ended up living with my one night stand woman for twelve years. There are a few stories to be told. Anyway, she switched from the pill to a foam contraceptive and we always had bareback sex. We ended up living on the west coast of Florida.

I did have two brief afternoon encounters with another woman during those twelve years and there is a story there. I think she must have been on the pill because I didn't think and she didn't say anything when we went bareback.

Near the end of my twelve year one night stand, I had a few interludes with an older woman - she must have been 50 - who had had a hysterectomy.

So, here I am at 40 having fucked a total of four women.

Having finally severed my relationship with the one night stand, I would have been homeless if my friend Bill had not offered me the spare bedroom in his apartment.

We were independent and did our own thing, went to work every day and sometimes talked in the evening if we were both there.

Bill had a steady squeeze and they had sex and spent the night together regularly. Sometimes at her place, sometimes at his place. I became used to seeing her around and listening to them have sex.

You can imagine my surprise when he told me on Friday morning that his friend Helen and a friend of hers were coming from the other coast for the weekend and would be staying with us. He ask me to keep the friend busy so he and Helen could make it a sexual weekend.

I never took into consideration what the sleeping arrangements would be.

Bill and Helen had met at a training conference and exchanged phone numbers, I think this was the first time they had seen each other since the conference and several months had passed.

The women arrived about 9 PM after a 4-5 hour drive. Both said they were tired after working all day and then driving across the state. They both had an overnight bag which they dropped along the living room wall when they came in.

One woman, in her 40's, was skinny, had a pock marked face, stringy hair and, in my opinion, not at all attractive.

The other woman was a big breasted, overweight red head 30 - 35 years old.

It turns out that Helen was the skinny one and she immediately went to Bill. they kissed and she said, "I've been waiting for this all day." Bill picked up her bag and she followed him into his bedroom. They closed the door and must have begun making out immediately as we could hear them through the door. They were both being very vocal and the walls were thin. In fact the lady in the apartment next door complained to management on Monday when the office opened.

Molly and I sat on the sofa and talked for the next hour or so about nothing. About 10:30 things in Bill's room became quiet and we figured that we would not see the other two until morning.

"What are the sleeping arrangements?" Molly ask.

"We just have this sofa and my bed. You can sleep here or use half of my bed."

"I'll sleep in the bed, but no sex."

"That's fine with me."

She used the hall bathroom to change into her sleep wear which consisted of a long, oversized T-shirt and her panties. I changed in the bedroom and wore a T-shirt and my briefs. I was on my side of the bed reading a book when she came back into the room.

She pulled her book out of her bag and came to bed. We read for a while and the sounds of our friends having another sexual experience came through the walls.

Molly put her book down and said, "I'm ready to sleep if you are."

"Sounds like a good idea."

I turned off the light and decided to do the gentlemanly thing under the circumstances and kiss her good night on the cheek.

"Good night Molly."

When I rolled over to kiss her cheek I inadvertently put my hand on her breast. It took up more space than I expected and really was not on purpose.

All this time the sounds of sex in the next bedroom were getting more intense.

"Oh what the hell! I'll have sex with you if you really want it." She leaned over and gave me a full mouth kiss. I didn't say anything, I just kissed back and slid my hands under her T-shirt. Molly had big, soft, natural breasts that felt like pillows with hard nipples. I had never felt breasts like these before. She seemed willing, so I pulled her T-shirt over her head to see what was there. She had a soft, flat stomach, but not fat. She wore big, loose clothing because of her big breasts but without her clothing she was quite attractive.

We explored each others' bodies. My T-shirt came off. She pulled down my briefs and I pulled down her panties which were beginning to get a bit damp. She had a neatly trimmed mound and yes, she was a true red head.

Her love honey tasted sooo good as I explored her womanhood with my tongue. I hadn't had sex in weeks and had gotten used to the situation. I had forgotten how nice it is to freely give and receive sexual pleasure.

She explored my cock, tasting the drops of pre-cum with her tongue.

I had two fingers in her and my thumb on her clit when she had her first orgasm. Molly was not a noisy partner but she was an appreciative partner. When she came I couldn't believe how wet and slippery my fingers became as they slid in and out of her pussy.

"Would you like to put my diaphragm in?"

"I have never done that. I don't know what to do."

"I'll show you." She went over to her bag and opened a small case which held something that looked like a small Frisbee. She squirted some goo on it from a tube and came back to bed. She lay down with her legs spread, squeezed the Frisbee in half and with her fingers pushed it into her vagina. She poked around a little bit, closed her legs, rolled over to me and said, "Just like that."

I was as hard as I have ever been and she was ready, so I positioned myself for missionary sex. As I slid the head of my penis into her love opening, she said, "Oh, that feels so good."

She rose to meet me as I plunged into her depths and soon we had a regular rhythm established. I guess she wanted her friend to know that we were having sex because suddenly she became much more vocal. "OH,OH. HARDER, HARDER." She had her second orgasm and I followed right after her, emptying weeks of accumulated cum deep into her open love tunnel.

In the morning we both awoke ready to resume where we had left off the night before. I had a morning woody and she had a morning itch that I didn't hesitate to take care of.

"Can we take a shower?" she asked.

We need to use the bathroom off the other bedroom. From the bacon smell it seems they are fixing breakfast and we shouldn't bother them."

She took my hand and we walked nude to the other bathroom. She wasn't shy and didn't care who saw us. I, on the other hand, was still very shy about my body and over the years very few people other than my sex partners, even on sports teams, had seen me nude.

We adjusted the water temperature and stepped into the shower. It was easily big enough for both of us, and we began soaping each other. I especially enjoyed washing her breasts and pussy with my hands. I guess she wanted to be sure she was totally clean because she washed her pussy also.

She cleaned my dick thoroughly. We kissed and hugged, full body, under the warm shower and then dried off. We hung up our shared towel and walked back to my bedroom nude. I don't know if they saw us or not because I didn't look in their direction.

We dressed and went out to the dining area for breakfast. We discussed plans for the day and decided we would tour the area on my motorcycle. She said, "I'll need to change my bra." We went into my bedroom and I sat on the bed while, with the door open, she stripped to the waist and put on what could only be described as a bullet proof bra. It was thick, heavy, and stiff, but it would prevent her breasts from bouncing around on our tour.

Molly was good at holding on and I could feel her breasts up against my back the entire time.

We stopped at a little waterfront grill for lunch and returned to the apartment in early afternoon. Our friends were still out so we had the place to ourselves.

"I need to change out of this bra."

I went into the bedroom with her and she whipped off her top and unfastened her bra. When I saw those soft pillow breasts again, I couldn't resist the temptation. While she was facing away from me to get her other bra, I put my arms around her with a hand cupping each breast. I hugged her. She turned around, kissed me with passion and said, "Let's do it now."

We both had our clothes off in moments and sank onto the bed together.

This time, after just a little kissing and hugging we joined our bodies together and experienced another nice orgasm together.

Still joined, me on top, we took a little nap until we heard our friends in the kitchen.

We reluctantly got dressed and joined our friends who were in the process of fixing dinner. We had a glass of wine and shared our experiences. No one even mentioned the good sex.

Bill and Helen were in bed when Molly and I went through to take another shower before going to bed. They were so engrossed with each other (Helen was on top) that they didn't even notice that we were nude also.

Sex with Molly was very satisfying again that night. Sometime along the way she told me that my penis was not as long as her boyfriends, but mine was nice and thick and filled her nicely.

Helen and Molly came to visit a few more times over the next months. They shared with us that on the drive over to our coast they talked about the great sex they were looking forward to.

I fell in love with my new Sally and did not see any more of Molly.